[{"antibiotic_name":"pyrazinamide","canonical_smiles":"C1=CN=C(C=N1)C(=O)N","cas_id":"98-96-4","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"IPEHBUMCGVEMRF-UHFFFAOYSA-N","molecular_formula":"C5H5N3O","molecular_weight":"123.115 g/mol","pubchem_cid":"1046","pubchem_cid_i":1046,"pharmacological_classes":["Established Pharmacologic Class [EPC]: Antimycobacterial"],"mechanism_of_action":["Pyrazinamide may be bacteriostatic or bactericidal in action, depending on the concentration of the drug attained at the site of the infection and the susceptibility of the infecting organism. In vitro and in vivo, the drug is active only at a slightly acidic pH. The exact mechanism of action of pyrazinamide has not been fully elucidated. The antimycobacterial activity of pyrazinamide appears to partly depend on conversion of the drug to pyrazinoic acid. Susceptible strains of Mycobacterium tuberculosis produce pyrazinamidase, an enzyme that deaminates pyrazinamide to pyrazinoic acid, and the in vitro susceptibility of a given strain of the organism appears to correspond to its pyrazinamidase activity. In vitro studies indicate that pyrazinoic acid has specific antimycobacterial activity against Mycobacterium tuberculosis. In addition, the fact that pyrazinoic acid lowers the pH of the environment below that which is necessary for growth of Mycobacterium tuberculosis appears to contribute to the drug's antimycobacterial activity in vitro.","Unknown; pyrazinamide may be bacteriostatic or bactericidal, depending on its concentration and the susceptibility of the organism. It is active in vitro at an acidic pH of 5.6 or less, similar to that found in early, active tubercular inflammatory lesions.","Pyrazinamide diffuses into M. tuberculosis, where the enzyme pyrazinamidase converts pyrazinamide to the active form pyrazinoic acid. Under acidic conditions, the pyrazinoic acid that slowly leaks out converts to the protonated conjugate acid, which is thought to diffuse easily back into the bacilli and accumulate. The net effect is that more pyrazinoic acid accumulates inside the bacillus at acid pH than at neutral pH. Pyrazinoic acid was thought to inhibit the enzyme fatty acid synthase (FAS) I, which is required by the bacterium to synthesise fatty acids. However, this theory was thought to have been discounted (PMID: 11914348). However, further studies reproduced the results of FAS I inhibition as the putative mechanism first in whole cell assay of replicating M. tuberculosis bacilli which have shown that pyrazinoic acid and its ester inhibit the synthesis of fatty acids (PMID: 17101678). This study was followed by in vitro assay of tuberculous FAS I enzyme that tested the activity with pyrazinamide, pyrazinoic acid and several classes of pyrazinamide analogs. Pyrazinamide and its analogs inhibited the activity of purified FAS I (PMID: 17485499). It has also been suggested that the accumulation of pyrazinoic acid disrupts membrane potential and interferes with energy production, necessary for survival of M. tuberculosis at an acidic site of infection. Pyrazinoic acid has also been shown to bind to the ribosomal protein S1 (RpsA) and inhibit trans-translation. This may explain the ability of the drug to kill dormant mycobacteria (PMID: 21835980)."],"synonyms":["Pyrazinamide","Tisamid"],"pharmacology":["Pyrazinamide kills or stops the growth of certain bacteria that cause tuberculosis (TB). It is used with other drugs to treat tuberculosis. It is a highly specific agent and is active only against Mycobacterium tuberculosis. In vitro and in vivo, the drug is active only at a slightly acid pH. Pyrazinamie gets activated to Pyrazinoic acid in the bacilli where it interferes with fatty acid synthase FAS I. This interferes with the bacteriums ability to synthesize new fatty acids, required for growth and replication.","Pyrazinamide is a synthetic pyrazinoic acid amide derivative with bactericidal property. Pyrazinamide is particularly active against slowly multiplying intracellular bacilli (unaffected by other drugs) by an unknown mechanism of action. Its bactericidal action is dependent upon the presence of bacterial pyrazinamidase, which removes the amide group to produce active pyrazinoic acid. Pyrazinamide is an important component of multidrug therapy for tuberculosis. (NCI04)"],"description":["A pyrazine that is used therapeutically as an antitubercular agent.","FDA Pharmacology Summary: Pyrazinamide is an Antimycobacterial.","Physical Description: PHYSICAL DESCRIPTION: White powder. Sublimes from 318°F. (NTP, 1992)","LiverTox Summary: Pyrazinamide is a first line antituberculosis medication, but is used only in combination with other antituberculosis medications such as isoniazid or rifampin. Pyrazinamide is associated with transient and asymptomatic elevations in serum aminotransferase levels and is a well known cause of clinically apparent, acute liver injury that can be severe and even fatal.","Metabolite Description: Pyrazinamide is only found in individuals that have used or taken this drug. It is a pyrazine that is used therapeutically as an antitubercular agent. Pyrazinamide is an important sterilizing prodrug that shortens tuberculosis (TB) therapy. However, the mechanism of action of pyrazinamide is poorly understood because of its unusual properties. In literature it has been written that the pyrazinoic acid (POA), the active moiety of pyrazinamide, disrupted membrane energetics and inhibited membrane transport function at acid pH in < i> Mycobacterium tuberculosis< /i> . The antimycobacterial activity appears to partly depend on conversion of the drug to POA. Susceptible strains of < i> M. tuberculosis< /i> produce pyrazinamidase, an enzyme that deaminates pyrazinamide to POA, and the vitro susceptibility of a given strain of the organism appears to correspond to its pyrazinamidase activity. Experimental evidence suggests that pyrazinamide diffuses into < i> M. tuberculosis< /i> in a passive manner, is converted into POA by pyrazinamidase, and because of an inefficient efflux system, accumulates in huge amounts in the bacterial cytoplasm. The accumulation of POA lowers the intracellular pH to a suboptimal level that is likely to inactivate a vital target enzyme such as fatty acid synthase. Recent studies (2007) demonstrated that pyrazinamide and its analogs inhibit the activity of purified FAS I.","Pharmacology: Pyrazinamide is a synthetic pyrazinoic acid amide derivative with bactericidal property. Pyrazinamide is particularly active against slowly multiplying intracellular bacilli (unaffected by other drugs) by an unknown mechanism of action. Its bactericidal action is dependent upon the presence of bacterial pyrazinamidase, which removes the amide group to produce active pyrazinoic acid. Pyrazinamide is an important component of multidrug therapy for tuberculosis. (NCI04)","A pyrazine that is used therapeutically as an antitubercular agent."],"atc_classification":["Antiinfectives for systemic use","Antimycobacterials","Drugs for treatment of tuberculosis","Other drugs for treatment of tuberculosis","Pyrazinamide"],"_version_":1809284005011390500},{"antibiotic_name":"bacitracin","canonical_smiles":"CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCCCCC(C(=O)NC(C(=O)N1)CCCN)NC(=O)C(C(C)CC)NC(=O)C(CCC(=O)O)NC(=O)C(CC(C)C)NC(=O)C2CSC(=N2)C(C(C)CC)N)CC(=O)N)CC(=O)O)CC3=CN=CN3)CC4=CC=CC=C4","cas_id":"22601-59-8","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"CLKOFPXJLQSYAH-ABRJDSQDSA-N","isomeric_smiles":"CC[C@H](C)[C@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)NCCCC[C@@H](C(=O)N[C@@H](C(=O)N1)CCCN)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]2CSC(=N2)[C@H]([C@@H](C)CC)N)CC(=O)N)CC(=O)O)CC3=CN=CN3)CC4=CC=CC=C4","molecular_formula":"C66H103N17O16S","molecular_weight":"1422.713 g/mol","pubchem_cid":"10909430","pubchem_cid_i":10909430,"mechanism_of_action":["Bacitracin intereferes with the dephosphorylation of the 55-carbon, biphosphate lipid transport molecule C55-isoprenyl pyrophosphate (undecaprenyl pyrophosphate), which carries the building blocks of the peptidoglycan bacterial cell wall outside the inner membrane for construction. Bacitracin binds divalent transition metal ions (Mn(II), Co(II), Ni(II), Cu(II), and Zn(II)) which binds and oxidatively cleave DNA.","Bacitracin interferes with bacterial cell wall synthesis and is active against many gram positive bacteria including staphylococci, streptococci, clostridia and Corynebacterium diphtheriae; It is also active against Treponema pallidum and some gram negative cocci.","Bacitracin may be bactericidal or bacteriostatic in action, depending on the concentration of the drug attained at the site of infection and the susceptibility of the infecting organism. Bacitracin inhibits bacterial cell wall synthesis by preventing the incorporation of amino acids and nucleotides into the cell wall. The drug probably interferes with the final dephosphorylation step in the phospholipid carrier cycle and in this manner bacitracin prevents the transfer of the mucopeptide to the growing cell wall. Bacitracin also damages the bacterial plasma membrane and is active against protoplasts."],"synonyms":["bacitracin A"],"pharmacology":["Bacitracin is a mixture of related cyclic polypeptides produced by organisms of the licheniformis group of Bacillus subtilis var Tracy. As a polypeptide, toxic, and difficult to use chemical, bacitracin doesn't work well orally, however is very effective topically. Bacitracin exerts pronounced antibacterial action in vitro against a variety of gram-positive and a few gram-negative organisms. However, among systemic diseases, only staphylococcal infections qualify for consideration of bacitracin therapy."],"description":["Bacitracin is a mixture of related cyclic polypeptides produced by organisms of the licheniformis group of Bacillus subtilis var Tracy. Its unique name derives from the fact that the bacillus producing it was first isolated in 1943 from a knee scrape from a girl named Margaret Tracy. As a toxic and difficult-to-use antibiotic, bacitracin doesn't work well orally. However, it is very effective topically. Bacitracin is synthesised via the so-called nonribosomal peptide synthetases (NRPSs), which means that ribosomes are not involved in its synthesis.","Metabolite Description: Bacitracin is a mixture of related cyclic polypeptides produced by organisms of the licheniformis group of Bacillus subtilis var Tracy. Its unique name derives from the fact that the bacillus producing it was first isolated in 1943 from a knee scrape from a girl named Margaret Tracy. As a toxic and difficult-to-use antibiotic, bacitracin doesn't work well orally. However, it is very effective topically. Bacitracin is synthesised via the so-called nonribosomal peptide synthetases (NRPSs), which means that ribosomes are not involved in its synthesis."],"_version_":1809284005049139200},{"antibiotic_name":"ampicillin/sulbactam","canonical_smiles":"CC1(C(C2C(S1(=O)=O)CC2=O)C(=O)O)C.CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C","cas_id":"94935-63-4","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"KMEGBUCIGMEPME-LQYKFRDPSA-N","isomeric_smiles":"CC1([C@@H](C2[C@H](S1(=O)=O)CC2=O)C(=O)O)C.CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)C","molecular_formula":"C25H31N3O9S2","molecular_weight":"581.655 g/mol","pubchem_cid":"119561","pubchem_cid_i":119561,"synonyms":["sulacillin"],"description":["LiverTox Summary: The combination of ampicillin and sulbactam sodium combines a third generation aminopenicillin and a beta-lactamase inhibitor and is used to treat serious bacterial infections due to susceptible organisms. Given parenterally, ampicillin and sulbactam can cause mild transient aminotransferase elevations and has been linked to very rare instances of acute liver injury."],"_version_":1809284005051236400},{"antibiotic_name":"teicoplanin","canonical_smiles":"CCCCCCCCCC(=O)NC1C(C(C(OC1OC2=C3C=C4C=C2OC5=C(C=C(C=C5)C(C6C(=O)NC(C7=CC(=CC(=C7C8=C(C=CC(=C8)C(C(=O)N6)NC(=O)C4NC(=O)C9C1=CC(=CC(=C1)O)OC1=C(C=CC(=C1)C(C(=O)NC(CC1=CC(=C(O3)C=C1)Cl)C(=O)N9)N)O)O)OC1C(C(C(C(O1)CO)O)O)O)O)C(=O)O)OC1C(C(C(C(O1)CO)O)O)NC(=O)C)Cl)CO)O)O","cas_id":"61036-62-2","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"BJNLLBUOHPVGFT-QRZIFLFXSA-N","isomeric_smiles":"CCCCCCCCCC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=C3C=C4C=C2OC5=C(C=C(C=C5)[C@H]([C@H]6C(=O)N[C@H](C7=CC(=CC(=C7C8=C(C=CC(=C8)[C@H](C(=O)N6)NC(=O)[C@@H]4NC(=O)[C@@H]9C1=CC(=CC(=C1)O)OC1=C(C=CC(=C1)[C@H](C(=O)N[C@H](CC1=CC(=C(O3)C=C1)Cl)C(=O)N9)N)O)O)O[C@@H]1[C@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)C(=O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)NC(=O)C)Cl)CO)O)O","molecular_formula":"C88H97Cl2N9O33","molecular_weight":"1879.674 g/mol","pubchem_cid":"16131923","pubchem_cid_i":16131923,"mechanism_of_action":["Teicoplanin inhibits peptidoglycan polymerization, resulting in inhibition of bacterial cell wall synthesis and cell death."],"synonyms":["Targocid","Teichomycin","Teichomycin A2","Teicoplanin"],"pharmacology":["Teicoplanin is an antibiotic used in the prophylaxis and treatment of serious infections caused by Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus and Enterococcus faecalis. It is a glycopeptide antiobiotic extracted from Actinoplanes teichomyceticus, with a similar spectrum of activity to vancomycin. Its mechanism of action is to inhibit bacterial cell wall synthesis. Oral teicoplanin has been demonstrated to be effective in the treatment of pseudomembranous colitis and Clostridium difficile-associated diarrhoea, with comparable efficacy to vancomycin."],"description":["Teicoplanin is a glycopeptide antibiotic. It is a mixture of several compounds, five major (named teicoplanin A2-1 through A2-5) and four minor (named teicoplanin RS-1 through RS-4). All teicoplanins share a same glycopeptide core, termed teicoplanin A3-1, a fused ring structure to which two carbohydrates (mannose and N-acetylglucosamine) are attached. The major and minor components also contain a third carbohydrate moiety, ?-D-glucosamine, and differ only by the length and conformation of a side chain attached to it. [Wikipedia]","Glycopeptide antibiotic complex from Actinoplanes teichomyceticus active against gram-positive bacteria. It consists of five major components each with a different fatty acid moiety."],"atc_classification":["Antiinfectives for systemic use","Antibacterials for systemic use","Other antibacterials","Glycopeptide antibacterials","Teicoplanin"],"_version_":1809284005052285000},{"antibiotic_name":"piperacillin/tazobactam","canonical_smiles":"CCN1CCN(C(=O)C1=O)C(=O)NC(C2=CC=CC=C2)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)[O-].CC1(C(N2C(S1(=O)=O)CC2=O)C(=O)O)CN3C=CN=N3.[Na+]","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"TUPFOYXHAYOHIB-WZGOVNIISA-M","isomeric_smiles":"CCN1CCN(C(=O)C1=O)C(=O)N[C@@H](C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)[O-].C[C@@]1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)O)CN3C=CN=N3.[Na+]","molecular_formula":"C33H38N9NaO12S2","molecular_weight":"839.828 g/mol","pubchem_cid":"23724843","pubchem_cid_i":23724843,"_version_":1809284005054382000},{"antibiotic_name":"cefixime","canonical_smiles":"C=CC1=C(N2C(C(C2=O)NC(=O)C(=NOCC(=O)O)C3=CSC(=N3)N)SC1)C(=O)O","cas_id":"79350-37-1","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"OKBVVJOGVLARMR-QSWIMTSFSA-N","isomeric_smiles":"C=CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\\OCC(=O)O)/C3=CSC(=N3)N)SC1)C(=O)O","molecular_formula":"C16H15N5O7S2","molecular_weight":"453.444 g/mol","pubchem_cid":"5362065","pubchem_cid_i":5362065,"pharmacological_classes":["Established Pharmacologic Class [EPC]: Cephalosporin Antibacterial","Chemical/Ingredient structural concept [Chemical/Ingredient]: Cephalosporins"],"mechanism_of_action":["Like all beta-lactam antibiotics, cefixime binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefixime interferes with an autolysin inhibitor."],"synonyms":["Anhydrous, Cefixime","Cefixime","Cefixime Anhydrous","Cefixime Trihydrate","FK 027","FK-027","FK027","FR 17027","FR-17027","FR17027","Suprax","Trihydrate, Cefixime"],"pharmacology":["Cefixime, an antibiotic, is a third-generation cephalosporin like ceftriaxone and cefotaxime. Cefixime is highly stable in the presence of beta-lactamase enzymes. As a result, many organisms resistant to penicillins and some cephalosporins due to the presence of beta-lactamases, may be susceptible to cefixime. The antibacterial effect of cefixime results from inhibition of mucopeptide synthesis in the bacterial cell wall."],"description":["Cefixime, an antibiotic, is a third-generation cephalosporin like ceftriaxone and cefotaxime. Cefixime is highly stable in the presence of beta-lactamase enzymes. As a result, many organisms resistant to penicillins and some cephalosporins due to the presence of beta-lactamases, may be susceptible to cefixime. The antibacterial effect of cefixime results from inhibition of mucopeptide synthesis in the bacterial cell wall.","FDA Pharmacology Summary: Cefixime anhydrous is a Cephalosporin Antibacterial. The chemical classification of cefixime anhydrous is Cephalosporins.","Metabolite Description: Cefixime, an antibiotic, is a third-generation cephalosporin like ceftriaxone and cefotaxime. Cefixime is highly stable in the presence of beta-lactamase enzymes. As a result, many organisms resistant to penicillins and some cephalosporins due to the presence of beta-lactamases, may be susceptible to cefixime. The antibacterial effect of cefixime results from inhibition of mucopeptide synthesis in the bacterial cell wall.","A third-generation cephalosporin antibiotic that is stable to hydrolysis by beta-lactamases."],"atc_classification":["Antiinfectives for systemic use","Antibacterials for systemic use","Other beta-lactam antibacterials","Third-generation cephalosporins","Cefixime"],"_version_":1809284005054382000},{"antibiotic_name":"oxytetracycline","canonical_smiles":"CC1(C2C(C3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O)O","cas_id":"79-57-2","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"OWFJMIVZYSDULZ-PXOLEDIWSA-N","isomeric_smiles":"C[C@@]1([C@H]2[C@@H]([C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O)O","molecular_formula":"C22H24N2O9","molecular_weight":"460.439 g/mol","pubchem_cid":"54675779","pubchem_cid_i":54675779,"pharmacological_classes":["Established Pharmacologic Class [EPC]: Tetracycline-class Antimicrobial","Chemical/Ingredient structural concept [Chemical/Ingredient]: Tetracyclines"],"mechanism_of_action":["Tetracyclines inhibit bacterial protein synthesis by binding to the 30 S bacterial ribosome and preventing access of aminoacyl tRNA to the acceptor (A) site on the mRNA-ribosome complex. They enter gram-negative bacteria by passive diffusion through the hydrophilic channels formed by the porin proteins of the outer cell membrane, and active transport by an energy-dependent system that pumps all tetracyclines across cytoplasmic membrane. Although permeation of these drugs into gram-positive bacteria is less well understood, it also is energy requiring. At high concn, these cmpd impair protein synthesis in mammalian cells. However, because mammalian cells lack the active transport system found in bacteria, and the ribosomal target is less sensitive, tetracyclines are selectively active against bacteria. /Tetracyclines/","The tetracycline antibiotics ... can produce neuromuscular blockade, possibly by chelation of Ca+2. /Tetracyclines/","Oxytetracycline inhibits cell growth by inhibiting translation. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. The binding is reversible in nature. Oxytetracycline is lipophilic and can easily pass through the cell membrane or passively diffuses through porin channels in the bacterial membrane."],"synonyms":["Anhydrous Oxytetracycline","Anhydrous, Oxytetracycline","Bisolvomycin","Calcium, Oxytetracycline","Dihydrate, Oxytetracycline","Geomycin","Hydrochloride, Oxytetracycline","Hydroxytetracycline","Monohydrochloride, Oxytetracycline","Oxyterracin","Oxyterracine","Oxytetracid","Oxytetracycline","Oxytetracycline Anhydrous","Oxytetracycline Calcium","Oxytetracycline Dihydrate","Oxytetracycline Hydrochloride","Oxytetracycline Monohydrochloride","Oxytetracycline Sulfate (2:1)","Oxytetracycline, (4a beta,5 beta,5a beta,12a beta)-Isomer","Oxytetracycline, (5 beta)-Isomer","Oxytetracycline, Anhydrous","Oxytetracycline, Calcium (1:1) Salt","Oxytetracycline, Disodium Salt, Dihydrate","Oxytetracycline, Sodium Salt","Sodium Salt Oxytetracycline","Terramycin"],"pharmacology":["Oxytetracycline is known as a broad-spectrum antibiotic due to its activity against such a wide range of infections. It was the second of the tetracyclines to be discovered. Oxytetracycline, like other tetracyclines, is used to treat many infections common and rare. Its better absorption profile makes it preferable to tetracycline for moderately severe acne, but alternatives sould be sought if no improvement occurs by 3 months."],"description":["A tetracycline analog isolated from the actinomycete streptomyces rimosus and used in a wide variety of clinical conditions. [PubChem]","FDA Pharmacology Summary: Oxytetracycline anhydrous is a Tetracycline-class Antimicrobial. The chemical classification of oxytetracycline anhydrous is Tetracyclines.","Physical Description: PHYSICAL DESCRIPTION: Odorless fluffy yellow solid or yellow powder. Bitter taste. (NTP, 1992)","A TETRACYCLINE analog isolated from the actinomycete STREPTOMYCES rimosus and used in a wide variety of clinical conditions."],"atc_classification":["Dermatologicals","Antibiotics and chemotherapeutics for dermatological use","Antibiotics for topical use","Tetracycline and derivatives","Oxytetracycline","Genito urinary system and sex hormones","Gynecological antiinfectives and antiseptics","Antiinfectives and antiseptics, excl. combinations with corticosteroids","Antibiotics","Oxytetracycline","Antiinfectives for systemic use","Antibacterials for systemic use","Tetracyclines","Tetracyclines","Oxytetracycline","Sensory organs","Ophthalmologicals","Antiinfectives","Antibiotics","Oxytetracycline"],"_version_":1809284005057527800},{"antibiotic_name":"cefpodoxime proxetil","canonical_smiles":"CC(C)OC(=O)OC(C)OC(=O)C1=C(CSC2N1C(=O)C2NC(=O)C(=NOC)C3=CSC(=N3)N)COC","cas_id":"87239-81-4","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"LTINZAODLRIQIX-FBXRGJNPSA-N","isomeric_smiles":"CC(C)OC(=O)OC(C)OC(=O)C1=C(CS[C@H]2N1C(=O)[C@H]2NC(=O)/C(=N\\OC)/C3=CSC(=N3)N)COC","molecular_formula":"C21H27N5O9S2","molecular_weight":"557.593 g/mol","pubchem_cid":"6526396","pubchem_cid_i":6526396,"synonyms":["1-(isopropoxycarbonyloxy)ethyl-7-(2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetamido)-3-methoxymethyl-8-oxo-5-thia-1-azabicyclo(4,2,0)-oct-2-ene-2-carboxylate","cefpodoxime proxetil","cephalosporin 807","CS 807","CS-807","Doxef","U 76252","U-76,252","Vantin"],"_version_":1809284005059625000},{"antibiotic_name":"doripenem","canonical_smiles":"CC1C2C(C(=O)N2C(=C1SC3CC(NC3)CNS(=O)(=O)N)C(=O)O)C(C)O","cas_id":"148016-81-3","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"AVAACINZEOAHHE-VFZPANTDSA-N","isomeric_smiles":"C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)CNS(=O)(=O)N)C(=O)O)[C@@H](C)O","molecular_formula":"C15H24N4O6S2","molecular_weight":"420.499 g/mol","pubchem_cid":"73303","pubchem_cid_i":73303,"pharmacological_classes":["Chemical/Ingredient structural concept [Chemical/Ingredient]: Carbapenems","Established Pharmacologic Class [EPC]: Penem Antibacterial"],"mechanism_of_action":["Doripenem is a broad-spectrum carbapenem antibiotic with activity against many gram-positive and gram-negative aerobic bacteria, as well as a variety of anaerobes. Like other beta-lactam antibiotics, doripenem's bactericidal mechanism of action is mostly due to cell death after inhibition of bacterial enzymes called penicillin-bindng proteins (PBPs), which are responsible for peptidoglycan cross-linking during the synthesis of the bacterial cell wall. Carbapenems mainly have high affinity for PBPs 1a, 1b, 2 and 3. Inhibition of each PBP usually results in a different inactivating mechanism. Inhibition of PBPs 1a and 1b results in fast bacterial killing through the formation of spheroplasts, inhibition of PBP 2 results in rod-shaped bacteria to become spherical, and inhibition of PBP 3 results in filamentous-shaped organisms. The PBPs preferentially bound by different carbapenems depend on the organism. In E.coli and P.aeruginosa, doripenem binds to PBP 2, which is involved in the maintenance of cell shape, as well as to PBPs 3 and 4. Doripenem has a 1-beta-methyl side chain, which allows it to be relatively resistant to dehydropeptidase, as well as a trans-alpha-1-hydroxyethyl group at position 6 which provides beta-lactamase resistance. Like other carbapenems, doripenem is different from most beta-lactams due to its stability against hydrolysis by most beta-lactamases, including penicillinases, cephalosporinases, ESBL, and Amp-C producing enterobacteriaceae."],"synonyms":["2-(5-sulfamoylaminomethylpyrrolidin-3-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylic acid","doripenem","S 4661","S-4661"],"pharmacology":["Similar to other beta-lactam antimicrobial agents, the time that unbound plasma concentration of doripenem exceeds the MIC (T>MIC) of the infecting organism has been shown to best correlate with efficacy in animal models of infection.","Doripenem is a broad-spectrum, carbapenem antibiotic with bactericidal and beta-lactamase resistant activities. Doripenem binds to penicillin binding proteins (PBPs) located on the bacterial cell wall, particularly PBPs 2 and 3, thereby inhibiting the final transpeptidation step in the synthesis of peptidoglycan, an essential component of the bacterial cell wall. Inhibition results in a weakening and eventually lysis of the bacterial cell wall. This agent is two- to 16-fold more potent than imipenem and comparable to ertapenem and meropenem."],"description":["Doripenem is a broad-spectrum, carbapenem antibiotic marketed under the brand name Doribax by Janssen. Doripenem injection was approved by the FDA in 2007 to treat complicated urinary tract and intra-abdominal infections. In a clinical trial of doripenem treatment in ventilator associated pneumonia (vs. imipenem and cilastatin), it was found that doripenem carried an increased risk of death and lower clinical cure rates, resulting in a premature termination of the trial. The FDA revised the doripenem label in 2014 to include a warning against use in ventilator-associated pneumonia and to reiterate its safety and efficacy for its approved indications.","FDA Pharmacology Summary: Doripenem is a Penem Antibacterial. The chemical classification of doripenem is Carbapenems.","LiverTox Summary: Doripenem is a broad spectrum carbapenem antibiotic used primarily for the treatment of aerobic gram-negative bacterial infections. Doripenem, like other carbapenems, is associated with transient and asymptomatic elevations in serum enzymes. The carbapenems have also been linked to rare instances of clinically apparent, acute cholestatic liver injury.","Pharmacology: Doripenem is a broad-spectrum, carbapenem antibiotic with bactericidal and beta-lactamase resistant activities. Doripenem binds to penicillin binding proteins (PBPs) located on the bacterial cell wall, particularly PBPs 2 and 3, thereby inhibiting the final transpeptidation step in the synthesis of peptidoglycan, an essential component of the bacterial cell wall. Inhibition results in a weakening and eventually lysis of the bacterial cell wall. This agent is two- to 16-fold more potent than imipenem and comparable to ertapenem and meropenem."],"atc_classification":["Antiinfectives for systemic use","Antibacterials for systemic use","Other beta-lactam antibacterials","Carbapenems","Doripenem"],"_version_":1809284005060673500},{"antibiotic_name":"imipenem","canonical_smiles":"CC(C1C2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O","cas_id":"74431-23-5","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"ZSKVGTPCRGIANV-ZXFLCMHBSA-N","isomeric_smiles":"C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O","molecular_formula":"C12H17N3O4S","molecular_weight":"299.345 g/mol","pubchem_cid":"104838","pubchem_cid_i":104838,"pharmacological_classes":["Chemical/Ingredient structural concept [Chemical/Ingredient]: Carbapenems","Established Pharmacologic Class [EPC]: Penem Antibacterial"],"mechanism_of_action":["Imipenem acts as an antimicrobial through the inhibition of cell wall synthesis of various gram-positive and gram-negative bacteria. This inhibition of cell wall synthesis in gram-negative bateria is attained by binding to pencillin binding proteins (PBPs). In E. coli and selected strains of P. aeruginosa, imipenem has shown to have the highest affinity to PBP-2, PBP-1a, and PBP-1b. This preferential binding to PBP-2 and PBP-1b results in the direct conversion of the individual cell to a spheroblast, which leads to rapid cell lysis and death without filament formation."],"synonyms":["Anhydrous Imipenem","Anhydrous, Imipenem","Imipemide","Imipenem","Imipenem Anhydrous","Imipenem, Anhydrous","MK 0787","MK-0787","MK0787","N Formimidoylthienamycin","N-Formimidoylthienamycin"],"pharmacology":["Imipenem is a beta-lactam antibiotic belongings to the subgroup of carbapenems. Imipenem has a broad spectrum of activity against aerobic and anaerobic Gram positive as well as Gram negative bacteria. It is particularly important for its activity against Pseudomonas aeruginosa and the Enterococcus species. Imipenem is rapidly degraded by the renal enzyme dehydropeptidase when administered alone, and is always co-administered with cilastatin to prevent this inactivation."],"description":["Semisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many multiresistant strains. It is stable to beta-lactamases. Clinical studies have demonstrated high efficacy in the treatment of infections of various body systems. Its effectiveness is enhanced when it is administered in combination with cilastatin, a renal dipeptidase inhibitor. [PubChem]","FDA Pharmacology Summary: Imipenem anhydrous is a Penem Antibacterial. The chemical classification of imipenem anhydrous is Carbapenems.","LiverTox Summary: Imipenem is a broad spectrum carbapenem antibiotic which is used for severe bacterial infections caused by susceptible organisms. Because imipenem is rapidly inactivated by renal dehydropeptidase I (DHP-1), it is given in combination with cilastatin, a DHP-I inhibitor which increases half-life and tissue penetration of imipenem. Parenterally administered imipenem/cilastatin has been associated with transient, mild serum aminotransferase elevations, but it is a rare cause of clinically apparent liver disease with jaundice.","Metabolite Description: Semisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many multiresistant strains. It is stable to beta-lactamases. Clinical studies have demonstrated high efficacy in the treatment of infections of various body systems. Its effectiveness is enhanced when it is administered in combination with cilastatin, a renal dipeptidase inhibitor. [PubChem]","Semisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many multiresistant strains. It is stable to beta-lactamases. Clinical studies have demonstrated high efficacy in the treatment of infections of various body systems. Its effectiveness is enhanced when it is administered in combination with CILASTATIN, a renal dipeptidase inhibitor."],"_version_":1809284005063819300},{"antibiotic_name":"florfenicol","canonical_smiles":"CS(=O)(=O)C1=CC=C(C=C1)C(C(CF)NC(=O)C(Cl)Cl)O","cas_id":"73231-34-2","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"AYIRNRDRBQJXIF-NXEZZACHSA-N","isomeric_smiles":"CS(=O)(=O)C1=CC=C(C=C1)[C@H]([C@@H](CF)NC(=O)C(Cl)Cl)O","molecular_formula":"C12H14Cl2FNO4S","molecular_weight":"358.205 g/mol","pubchem_cid":"114811","pubchem_cid_i":114811,"synonyms":["3-fluorothiamphenicol","chloramphen","florfenicol","florphenicol","Sch 25298","Sch-25298","thiamphenicol, 3-fluoro"],"_version_":1809284005065916400},{"antibiotic_name":"synercid","canonical_smiles":"CCC1C(=O)N2CCCC2C(=O)N(C(C(=O)N3CC(C(=O)CC3C(=O)NC(C(=O)OC(C(C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CSC6CN7CCC6CC7)CC8=CC=C(C=C8)N(C)C)C.CCN(CC)CCS(=O)(=O)C1CCN2C1C(=O)OC(C(C=CC(=O)NCC=CC(=CC(CC(=O)CC3=NC(=CO3)C2=O)O)C)C)C(C)C","cas_id":"126602-89-9","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"PPKJUHVNTMYXOD-GKSTYDNOSA-N","isomeric_smiles":"CC[C@@H]1C(=O)N2CCC[C@H]2C(=O)N([C@H](C(=O)N3C[C@H](C(=O)CC3C(=O)N[C@H](C(=O)O[C@@H]([C@@H](C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CS[C@@H]6CN7CCC6CC7)CC8=CC=C(C=C8)N(C)C)C.CCN(CC)CCS(=O)(=O)[C@@H]1CCN2[C@H]1C(=O)O[C@@H]([C@@H](/C=C/C(=O)NC/C=C/C(=C/[C@H](CC(=O)CC3=NC(=CO3)C2=O)O)/C)C)C(C)C","molecular_formula":"C87H117N13O19S2","molecular_weight":"1713.085 g/mol","pubchem_cid":"11979418","pubchem_cid_i":11979418,"synonyms":["quinupristin-dalfopristin","RP 59500","RP-59500","Synercid"],"description":["LiverTox Summary: Quinupristin and dalfopristin are intravenously administered, streptogramin antibiotics used in fixed combination to treat severe bacterial infections due to susceptible organisms including methicillin resistant Staphylococcus aureus (MRSA). The fixed combination of quinupristin and dalfopristin is associated with a low rate of serum enzyme elevations during therapy but has not been convincingly linked to instances of clinically apparent liver injury."],"_version_":1809284005065916400},{"antibiotic_name":"erythromycin","canonical_smiles":"CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)O)(C)O","cas_id":"114-07-8","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"ULGZDMOVFRHVEP-RWJQBGPGSA-N","isomeric_smiles":"CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O","molecular_formula":"C37H67NO13","molecular_weight":"733.937 g/mol","pubchem_cid":"12560","pubchem_cid_i":12560,"pharmacological_classes":["Physiologic Effects [PE]: Decreased Sebaceous Gland Activity","Established Pharmacologic Class [EPC]: Macrolide","Established Pharmacologic Class [EPC]: Macrolide Antimicrobial","Chemical/Ingredient structural concept [Chemical/Ingredient]: Macrolides"],"mechanism_of_action":["Macrolide antibiotics are bacteriostatic agents that inhibit protein synthesis by binding reversibly to 50S ribosomal subunits of sensitive microorganisms, at or very near the site that binds chloramphenicol. Erythromycin does not inhibit peptide bond formation per se, but rather inhibits the translocation step wherein a newly synthesized peptidyl tRNA molecule moves from the acceptor site on the ribosome to the peptidyl donor site. Gram-positive bacteria accumulate about 100 times more erythromycin than do gram-negative bacteria. Cells are considerably more permeable to the un-ionized form of the drug, which probably explains the increased antimicrobial activity at alkaline pH.","... /Erythromycin/ inhibits the growth of susceptible organisms (principally Propionibacterium acnes) on the surface of the skin and reduces the concn of free fatty acids in sebum ... The reduction in free fatty acids in sebum may be an indirect result of the inhibition of lipase-producing organisms which convert triglycerides into free fatty acids or may be a direct result of interference with lipase production in these organisms. /In acne treatment regimens/","Although stromal-derived factor-1 (SDF-1) via its cognate receptor CXCR4 is assumed to play a critical role in migration of endothelial cells during new vessel formation after tissue injury, CXCR4 expression on endothelial cells is strictly regulated. Erythromycin (EM), a 14-membered ring macrolide, has an anti-inflammatory effect that may account for its clinical benefit in the treatment of chronic inflammatory diseases. However, the effects of EM on endothelial cells and especially their expression of CXCR4 have not been fully evaluated. In this study, we demonstrated that EM markedly induced CXCR4 surface expression on microvascular endothelial cells in vitro and lung capillary endothelial cells in vivo. This ability to induce CXCR4 surface expression on endothelial cells was restricted to 14-membered ring macrolides and was not observed in other antibiotics including a 16-membered ring macrolide, josamycin. Furthermore, this EM-induced expression of CXCR4 on endothelial cells was functionally significant as demonstrated by chemotaxis assays in vitro. These findings suggest that EM-induced CXCR4 surface expression on endothelial cells may promote migration of CXCR4-expressing endothelial cells into sites of tissue injury, which may be associated with the known anti-inflammatory activity of this macrolide.","Erythromycin acts by penetrating the bacterial cell membrane and reversibly binding to the 50 S subunit of bacterial ribosomes or near the “P” or donor site so that binding of tRNA (transfer RNA) to the donor site is blocked. Translocation of peptides from the “A” or acceptor site to the “P” or donor site is prevented, and subsequent protein synthesis is inhibited. Erythromycin is effective only against actively dividing organisms. The exact mechanism by which erythmromycin reduces lesions of acne vulgaris is not fully known: however, the effect appears to be due in part to the antibacterial activity of the drug."],"synonyms":["Erycette","Erymax","Erythromycin","Erythromycin A","Erythromycin C","Erythromycin Lactate","Erythromycin Phosphate","Ilotycin","Lactate, Erythromycin","Phosphate, Erythromycin","T Stat","T-Stat","TStat"],"pharmacology":["Erythromycin is produced by a strain of Streptomyces erythraeus and belongs to the macrolide group of antibiotics. After absorption, erythromycin diffuses readily into most body fluids. In the absence of meningeal inflammation, low concentrations are normally achieved in the spinal fluid, but the passage of the drug across the blood-brain barrier increases in meningitis. Erythromycin is excreted in breast milk. The drug crosses the placental barrier with fetal serum drug levels reaching 5 - 20% of maternal serum concentrations. Erythromycin is not removed by peritoneal dialysis or hemodialysis.","Erythromycin is a broad-spectrum, macrolide antibiotic with antibacterial activity. Erythromycin diffuses through the bacterial cell membrane and reversibly binds to the 50S subunit of the bacterial ribosome. This prevents bacterial protein synthesis. Erythromycin may be bacteriostatic or bactericidal in action, depending on the concentration of the drug at the site of infection and the susceptibility of the organism involved."],"description":["Erythromycin is a macrolide antibiotic produced by Streptomyces erythreus. It inhibits bacterial protein synthesis by binding to bacterial 50S ribosomal subunits; binding inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins. Erythromycin may be bacteriostatic or bactericidal depending on the organism and drug concentration.","FDA Pharmacology Summary: Erythromycin is a Macrolide and Macrolide Antimicrobial. The physiologic effect of erythromycin is by means of Decreased Sebaceous Gland Activity. The chemical classification of erythromycin is Macrolides.","Physical Description: PHYSICAL DESCRIPTION: Fluffy colorless powder or fine white powder. (NTP, 1992)","LiverTox Summary: Erythromycin is an oral macrolide antibiotic that has been in common use since the 1950s. Erythromycin has been linked to rare instances of acute liver injury that are usually self-limited, but can result in severe injury and death.","Metabolite Description: Erythromycin is a macrolide antibiotic produced by Streptomyces erythreus. It inhibits bacterial protein synthesis by binding to bacterial 50S ribosomal subunits; binding inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins. Erythromycin may be bacteriostatic or bactericidal depending on the organism and drug concentration.","Pharmacology: Erythromycin is a broad-spectrum, macrolide antibiotic with antibacterial activity. Erythromycin diffuses through the bacterial cell membrane and reversibly binds to the 50S subunit of the bacterial ribosome. This prevents bacterial protein synthesis. Erythromycin may be bacteriostatic or bactericidal in action, depending on the concentration of the drug at the site of infection and the susceptibility of the organism involved.","A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins."],"atc_classification":["Dermatologicals","Anti-acne preparations","Anti-acne preparations for topical use","Antiinfectives for treatment of acne","Erythromycin","Antiinfectives for systemic use","Antibacterials for systemic use","Macrolides, lincosamides and streptogramins","Macrolides","Erythromycin","Sensory organs","Ophthalmologicals","Antiinfectives","Antibiotics","Erythromycin"],"_version_":1809284005066965000},{"antibiotic_name":"ethambutol","canonical_smiles":"CCC(CO)NCCNC(CC)CO","cas_id":"74-55-5","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"AEUTYOVWOVBAKS-UWVGGRQHSA-N","isomeric_smiles":"CC[C@@H](CO)NCCN[C@@H](CC)CO","molecular_formula":"C10H24N2O2","molecular_weight":"204.314 g/mol","pubchem_cid":"14052","pubchem_cid_i":14052,"pharmacological_classes":["Established Pharmacologic Class [EPC]: Antimycobacterial"],"mechanism_of_action":["Ethambutol is bacteriostatic in action. Although the exact mechanism of action has not been fully elucidated, the drug appears to inhibit the synthesis of one or more metabolites in susceptible bacteria resulting in impairment of cellular metabolism, arrest of multiplication, and cell death. Ethambutol is active against susceptible bacteria only when they are undergoing cell division.","Ethambutol inhibits arabinosyl transferases which is involved in cell wall biosynthesis. By inhibiting this enzyme, the bacterial cell wall complex production is inhibited. This leads to an increase in cell wall permeability."],"synonyms":["Dexambutol","EMB Fatol","EMB Hefa","EMB-Fatol","EMB-Hefa","Etambutol Llorente","Ethambutol","Ethambutol Hydrochloride","Etibi","Hydrochloride, Ethambutol","Llorente, Etambutol","Miambutol","Myambutol"],"pharmacology":["Ethambutol is an oral chemotherapeutic agent which is specifically effective against actively growing microorganisms of the genus Mycobacterium, including M. tuberculosis. Ethambutol inhibits RNA synthesis and decreases tubercle bacilli replication. Nearly all strains of M. tuberculosis and M. kansasii as well as a number of strains of MAC are sensitive to ethambutol.","Ethambutol is an antibiotic with bacteriostatic, antimicrobial and antitubercular properties. Ethambutol interferes with the biosynthesis of arabinogalactan, a major polysaccharide of the mycobacterial cell wall. It inhibits the polymerization of cell wall arabinan of arabinogalactan and lipoarabinomannan by blocking arabinosyl transferases and induces the accumulation of D-arabinofuranosyl-P-decaprenol, an intermediate in arabinan biosynthesis. This results in halting bacterial growth."],"description":["An antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect. (From Smith and Reynard, Textbook of Pharmacology, 1992, p863)","FDA Pharmacology Summary: Ethambutol is an Antimycobacterial.","LiverTox Summary: Ethambutol is a first line but adjunctive antituberculosis medication which is used only in combination with other agents such as isoniazid and rifampin. Ethambutol therapy has been associated with minor, transient and asymptomatic elevations in serum aminotransferase levels, but is a rare cause of clinically apparent acute liver injury.","Metabolite Description: An antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect. (From Smith and Reynard, Textbook of Pharmacology, 1992, p863)","Pharmacology: Ethambutol is an antibiotic with bacteriostatic, antimicrobial and antitubercular properties. Ethambutol interferes with the biosynthesis of arabinogalactan, a major polysaccharide of the mycobacterial cell wall. It inhibits the polymerization of cell wall arabinan of arabinogalactan and lipoarabinomannan by blocking arabinosyl transferases and induces the accumulation of D-arabinofuranosyl-P-decaprenol, an intermediate in arabinan biosynthesis. This results in halting bacterial growth.","An antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect. (From Smith and Reynard, Textbook of Pharmacology, 1992, p863)"],"atc_classification":["Antiinfectives for systemic use","Antimycobacterials","Drugs for treatment of tuberculosis","Other drugs for treatment of tuberculosis","Ethambutol"],"_version_":1809284005070110700},{"antibiotic_name":"levofloxacin","canonical_smiles":"CC1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O","cas_id":"100986-85-4","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"GSDSWSVVBLHKDQ-JTQLQIEISA-N","isomeric_smiles":"C[C@H]1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O","molecular_formula":"C18H20FN3O4","molecular_weight":"361.373 g/mol","pubchem_cid":"149096","pubchem_cid_i":149096,"mechanism_of_action":["Levofloxacin is the L-isomer of the racemate, ofloxacin, a quinolone antimicrobial agent. The antibacterial activity of ofloxacin resides primarily in the L-isomer. The mechanism of action of levofloxacin and other fluoroquinolone antimicrobials involves inhibition of bacterial topoisomerase IV and DNA gyrase (both of which are type II topoisomerases), enzymes required for DNA replication, transcription, repair and recombination.","Fluoroquinolones prolong the QT interval by blocking voltage-gated potassium channels, especially the rapid component of the delayed rectifier potassium current I(Kr), expressed by HERG (the human ether-a-go-go-related gene). According to the available case reports and clinical studies, moxifloxacin carries the greatest risk of QT prolongation from all available quinolones in clinical practice and it should be used with caution in patients with predisposing factors for Torsades de pointes (TdP).","Levofloxacin inhibits bacterial type II topoisomerases, topoisomerase IV and DNA gyrase. Levofloxacin, like other fluoroquinolones, inhibits the A subunits of DNA gyrase, two subunits encoded by the gyrA gene. This results in strand breakage on a bacterial chromosome, supercoiling, and resealing; DNA replication and transcription is inhibited."],"synonyms":["Anhydrous, Levofloxacin","Levaquin","Levofloxacin","Levofloxacin Anhydrous","Ofloxacin, (S)-Isomer","Quixin"],"pharmacology":["Levofloxacin, a fluoroquinolone antiinfective, is the optically active L-isomer of ofloxacin. Levofloxacin is used to treat bacterial conjunctivitis, sinusitis, chronic bronchitis, community-acquired pneumonia and pneumonia caused by penicillin-resistant strains of Streptococcus pneumoniae, skin and skin structure infections, complicated urinary tract infections and acute pyelonephritis."],"description":["A synthetic fluoroquinolone (fluoroquinolones) antibacterial agent that inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication. [PubChem]","LiverTox Summary: Levofloxacin is a third generation fluoroquinolone that is widely used in the treatment of mild-to-moderate respiratory and urinary tract infections due to sensitive organisms. Levofloxacin has been linked to rare instances of clinically apparent hepatic injury marked by a short latency period and a hepatocellular pattern of enzyme elevations, similar to what has been described with ciprofloxacin.","Metabolite Description: Levofloxacin is a synthetic fluoroquinolone antibacterial agent that inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication. Levofloxacin is marketed by Ortho-McNeil under the trade name Levaquin. Chemically, levofloxacin is the S-enantiomer (L-isomer) of ofloxacin. -- Wikipedia.","The L-isomer of Ofloxacin."],"atc_classification":["Antiinfectives for systemic use","Antibacterials for systemic use","Quinolone antibacterials","Fluoroquinolones","Levofloxacin","Sensory organs","Ophthalmologicals","Antiinfectives","Fluoroquinolones","Levofloxacin"],"_version_":1809284005072208000},{"antibiotic_name":"vancomycin","canonical_smiles":"CC1C(C(CC(O1)OC2C(C(C(OC2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)C(C(C(=O)NC(C(=O)NC5C(=O)NC7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9C(NC(=O)C(C(C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)O)O)CC(=O)N)NC(=O)C(CC(C)C)NC)O)Cl)CO)O)O)(C)N)O","cas_id":"1404-90-6","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"MYPYJXKWCTUITO-LYRMYLQWSA-N","isomeric_smiles":"C[C@H]1[C@H]([C@@](C[C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H]5C(=O)N[C@@H]7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9[C@H](NC(=O)[C@H]([C@@H](C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl)CO)O)O)(C)N)O","molecular_formula":"C66H75Cl2N9O24","molecular_weight":"1449.265 g/mol","pubchem_cid":"14969","pubchem_cid_i":14969,"pharmacological_classes":["Established Pharmacologic Class [EPC]: Glycopeptide Antibacterial","Chemical/Ingredient structural concept [Chemical/Ingredient]: Glycopeptides"],"mechanism_of_action":["Vancomycin is bactericidal and appears to bind to the bacterial cell wall causing blockage of glycopeptide polymerization. This effect, which occurs at a site different from that affected by the penicillins, produces immediate inhibition of cell wall synthesis and secondary damage to the cytoplasmic membrane. Magnesium, manganese, calcium, and ferrous ions reduce the degree of adsorption of vancomycin to the cell wall, but the in vivo importance of this interaction is unknown.","The bactericidal action of vancomycin results primarily from inhibition of cell-wall biosynthesis. In addition, vancomycin alters bacterial-cell-membrane permeability and RNA synthesis.","The bactericidal action of vancomycin results primarily from inhibition of cell-wall biosynthesis. Specifically, vancomycin prevents incorporation of N-acetylmuramic acid (NAM)- and N-acetylglucosamine (NAG)-peptide subunits from being incorporated into the peptidoglycan matrix; which forms the major structural component of Gram-positive cell walls. The large hydrophilic molecule is able to form hydrogen bond interactions with the terminal D-alanyl-D-alanine moieties of the NAM/NAG-peptides. Normally this is a five-point interaction. This binding of vancomycin to the D-Ala-D-Ala prevents the incorporation of the NAM/NAG-peptide subunits into the peptidoglycan matrix. In addition, vancomycin alters bacterial-cell-membrane permeability and RNA synthesis. There is no cross-resistance between vancomycin and other antibiotics. Vancomycin is not active in vitro against gram-negative bacilli, mycobacteria, or fungi."],"synonyms":["AB-Vancomycin","Diatracin","Hydrochloride, Vancomycin","Sulfate, Vancomycin","Vanco Azupharma","VANCO-cell","Vanco-saar","Vancocin","Vancocin HCl","Vancocine","Vancomicina Abbott","Vancomicina Chiesi","Vancomicina Combino Phar","Vancomicina Norman","Vancomycin","Vancomycin Hexal","Vancomycin Hydrochloride","Vancomycin Lilly","Vancomycin Phosphate (1:2)","Vancomycin Phosphate (1:2), Decahydrate","Vancomycin Sulfate","Vancomycin-ratiopharm","Vancomycine Dakota"],"pharmacology":["Vancomycin is a branched tricyclic glycosylated nonribosomal peptide produced by the fermentation of the Actinobacteria species Amycolatopsis orientalis (formerly Nocardia orientalis). It is often reserved as the \"drug of last resort\", used only after treatment with other antibiotics had failed. Vancomycin has been shown to be active against most strains of the following microorganisms, both in vitro and in clinical infections: Listeria monocytogenes, Streptococcus pyogenes, Streptococcus pneumoniae (including penicillin-resistant strains), Streptococcus agalactiae, Actinomyces species, and Lactobacillus species. The combination of vancomycin and an aminoglycoside acts synergistically in vitro against many strains of Staphylococcus aureus, Streptococcus bovis, enterococci, and the viridans group streptococci.","Vancomycin is a branched tricyclic glycosylated peptide with bactericidal activity against most organisms and bacteriostatic effect on enterococci. At a site different from that of penicillins and cephalosporins, vancomycin binds tightly to the D-alanyl-D-alanine portion of cell wall precursors, thereby interfering with bacterial cell wall synthesis. This leads to activation of bacterial autolysins that destroy the cell wall by lysis. Vancomycin may also alter the permeability of bacterial cytoplasmic membranes and may selectively inhibit RNA synthesis."],"description":["Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to ristocetin that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear. [PubChem]","FDA Pharmacology Summary: Vancomycin is a Glycopeptide Antibacterial. The chemical classification of vancomycin is Glycopeptides.","LiverTox Summary: Information Vancomycin is a broad spectrum antibiotic that has activity against methicillin-resistant strains of Staphylococcus aureus and is generally reserved for serious drug resistant gram-positive infections. Vancomycin therapy has been linked many to instances of hypersensitivity with fever, rash and eosinophilia that can be associated with mild hepatic injury, but despite over 50 years of use, it has not been linked to cases of serious hepatotoxicity.","Metabolite Description: Vancomycin is only found in individuals that have used or taken this drug. It is an antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to ristocetin that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear. [PubChem]The bactericidal action of vancomycin results primarily from inhibition of cell-wall biosynthesis. Specifically, vancomycin prevents incorporation of N-acetylmuramic acid (NAM)- and N-acetylglucosamine (NAG)-peptide subunits from being incorporated into the peptidoglycan matrix; which forms the major structural component of Gram-positive cell walls. The large hydrophilic molecule is able to form hydrogen bond interactions with the terminal D-alanyl-D-alanine moieties of the NAM/NAG-peptides. Normally this is a five-point interaction. This binding of vancomycin to the D-Ala-D-Ala prevents the incorporation of the NAM/NAG-peptide subunits into the peptidoglycan matrix. In addition, vancomycin alters bacterial-cell-membrane permeability and RNA synthesis. There is no cross-resistance between vancomycin and other antibiotics. Vancomycin is not active in vitro against gram-negative bacilli, mycobacteria, or fungi.","Pharmacology: Vancomycin is a branched tricyclic glycosylated peptide with bactericidal activity against most organisms and bacteriostatic effect on enterococci. At a site different from that of penicillins and cephalosporins, vancomycin binds tightly to the D-alanyl-D-alanine portion of cell wall precursors, thereby interfering with bacterial cell wall synthesis. This leads to activation of bacterial autolysins that destroy the cell wall by lysis. Vancomycin may also alter the permeability of bacterial cytoplasmic membranes and may selectively inhibit RNA synthesis.","Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to RISTOCETIN that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear."],"atc_classification":["Alimentary tract and metabolism","Antidiarrheals, intestinal antiinflammatory/antiinfective agents","Intestinal antiinfectives","Antibiotics","Vancomycin","Antiinfectives for systemic use","Antibacterials for systemic use","Other antibacterials","Glycopeptide antibacterials","Vancomycin"],"_version_":1809284005074305000},{"antibiotic_name":"ertapenem","canonical_smiles":"CC1C2C(C(=O)N2C(=C1SC3CC(NC3)C(=O)NC4=CC=CC(=C4)C(=O)O)C(=O)O)C(C)O","cas_id":"153832-46-3","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"JUZNIMUFDBIJCM-ANEDZVCMSA-N","isomeric_smiles":"C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)NC4=CC=CC(=C4)C(=O)O)C(=O)O)[C@@H](C)O","molecular_formula":"C22H25N3O7S","molecular_weight":"475.516 g/mol","pubchem_cid":"150610","pubchem_cid_i":150610,"pharmacological_classes":["Chemical/Ingredient structural concept [Chemical/Ingredient]: Carbapenems","Established Pharmacologic Class [EPC]: Penem Antibacterial"],"mechanism_of_action":["Ertapenem is a synthetic carbapenem beta-lactam antibiotic that is structurally and pharmacologically related to imipenem and meropenem. Like meropenem but unlike imipenem, ertapenem has a methyl group at position 1 of the 5-membered ring, which confers stability against hydrolysis by dehydropeptidase 1 (DHP 1) present on the brush border of proximal renal tubular cells, and therefore does not require concomitant administration with a DHP-1 inhibitor such as cilastatin.","Ertapenem has in vitro activity against Gram-positive and Gram-negative aerobic and anaerobic bacteria. The bactericidal activity of ertapenem results from the inhibition of cell wall synthesis and is mediated through ertapenem binding to penicillin binding proteins (PBPs). In Escherichia coli, it has strong affinity toward PBPs 1a, 1b, 2, 3, 4 and 5 with preference for PBPs 2 and 3.","Antimicrobials are the most frequently implicated class of drugs in drug-induced seizure, with beta-lactams being the class of antimicrobials most often implicated. The seizure-inducing potential of the carbapenem subclass may be directly related to their beta-lactam ring structure. Data on individual carbapenems and seizure activity are scarce. To evaluate the available evidence on the association between carbapenem agents and seizure activity, /investigators/ conducted a literature search of the MEDLINE (1966-May 2010), EMBASE (1974-May 2010), and International Pharmaceutical Abstracts (1970-May 2010) databases. Reference citations from the retrieved articles were also reviewed. Mechanistically, seizure propensity of the beta-lactams is related to their binding to gamma-aminobutyric acid (GABA) receptors. There are numerous reports of seizure activity associated with imipenem-cilastatin, with seizure rates ranging from 3-33%. For meropenem, doripenem, and ertapenem, the seizure rate for each agent is reported as less than 1%. However, as their use increases and expands into new patient populations, the rate of seizures with these agents may increase. High-dose therapy, especially in patients with renal dysfunction, preexisting central nervous system abnormalities, or a seizure history increases the likelihood of seizure activity. ...","The bactericidal activity of ertapenem results from the inhibition of cell wall synthesis and is mediated through ertapenem binding to penicillin binding proteins (PBPs). In Escherichia coli, it has strong affinity toward PBPs 1a, 1b, 2, 3, 4 and 5 with preference for PBPs 2 and 3. Ertapenem is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases. Ertapenem is hydrolyzed by metallo-beta-lactamases."],"synonyms":["ertapenem","ertapenem sodium","Invanoz","Invanz"],"pharmacology":["Ertapenem has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria.","Ertapenem is a 1-beta-methyl carbapenem and broad-spectrum beta-lactam antibiotic with bactericidal property. Ertapenem binds to penicillin binding proteins (PBPs) located on the bacterial cell wall, in particular PBPs 2 and 3, thereby inhibiting the final transpeptidation step in the synthesis of peptidoglycan, an essential component of the bacterial cell wall. Inhibition results in a weakening and subsequent lysis of the cell wall leading to cell death of Gram-positive and Gram-negative aerobic and anaerobic pathogens. This agent is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, cephalosporinases and extended-spectrum beta-lactamases."],"description":["Ertapenem is a carbapenem antibiotic marketed by Merck as Invanz®. It is structurally very similar to meropenem in that it possess a 1-beta-methyl group. [Wikipedia]","FDA Pharmacology Summary: Ertapenem is a Penem Antibacterial. The chemical classification of ertapenem is Carbapenems.","LiverTox Summary: Ertapenem is a broad spectrum carbapenem antibiotic used primarily for the treatment of aerobic gram-negative bacterial infections. Ertapenem, like other carbapenems, is associated with transient and asymptomatic elevations in serum enzymes. The carbapenems have also been linked to rare instances of clinically apparent, acute cholestatic liver injury.","Metabolite Description: Ertapenem is only found in individuals that have used or taken this drug. It is a carbapenem antibiotic marketed by Merck as Invanz& reg. It is structurally very similar to meropenem in that it possess a 1-beta-methyl group. [Wikipedia]The bactericidal activity of ertapenem results from the inhibition of cell wall synthesis and is mediated through ertapenem binding to penicillin binding proteins (PBPs). In < i> Escherichia coli< /i> , it has strong affinity toward PBPs 1a, 1b, 2, 3, 4 and 5 with preference for PBPs 2 and 3. Ertapenem is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases. Ertapenem is hydrolyzed by metallo-beta-lactamases.","Pharmacology: Ertapenem is a 1-beta-methyl carbapenem and broad-spectrum beta-lactam antibiotic with bactericidal property. Ertapenem binds to penicillin binding proteins (PBPs) located on the bacterial cell wall, in particular PBPs 2 and 3, thereby inhibiting the final transpeptidation step in the synthesis of peptidoglycan, an essential component of the bacterial cell wall. Inhibition results in a weakening and subsequent lysis of the cell wall leading to cell death of Gram-positive and Gram-negative aerobic and anaerobic pathogens. This agent is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, cephalosporinases and extended-spectrum beta-lactamases."],"atc_classification":["Antiinfectives for systemic use","Antibacterials for systemic use","Other beta-lactam antibacterials","Carbapenems","Ertapenem"],"_version_":1809284005079548000},{"antibiotic_name":"moxifloxacin","canonical_smiles":"COC1=C2C(=CC(=C1N3CC4CCCNC4C3)F)C(=O)C(=CN2C5CC5)C(=O)O","cas_id":"354812-41-2","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"FABPRXSRWADJSP-MEDUHNTESA-N","isomeric_smiles":"COC1=C2C(=CC(=C1N3C[C@@H]4CCCN[C@@H]4C3)F)C(=O)C(=CN2C5CC5)C(=O)O","molecular_formula":"C21H24FN3O4","molecular_weight":"401.438 g/mol","pubchem_cid":"152946","pubchem_cid_i":152946,"pharmacological_classes":["Established Pharmacologic Class [EPC]: Quinolone Antimicrobial","Chemical/Ingredient structural concept [Chemical/Ingredient]: Quinolones"],"mechanism_of_action":["The bactericidal action of moxifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV. DNA gyrase is an essential enzyme that is involved in the replication, transcription and repair of bacterial DNA. Topoisomerase IV is an enzyme known to play a key role in the partitioning of the chromosomal DNA during bacterial cell division.","The fluoroquinolone antibiotic moxifloxacin has been associated with the acquired long QT syndrome and is used as a positive control in the evaluation of the QT-interval prolonging potential of new drugs. In common with other QT-prolonging agents, moxifloxacin is known to inhibit the hERG potassium K+ channel, but at present there is little mechanistic information available on this action. This study was conducted in order to characterise the inhibition of hERG current (I(hERG)) by moxifloxacin, and to determine the role in drug binding of the S6 aromatic amino-acid residues Tyr652 and Phe656. hERG currents were studied using whole-cell patch clamp (at room temperature and at 35-37 degrees C) in an HEK293 cell line stably expressing hERG channels. Moxifloxacin reversibly inhibited currents in a dose-dependent manner. We investigated the effects of different voltage commands to elicit hERG currents on moxifloxacin potency. Using a 'step-ramp' protocol, the IC50 was 65 uM at room temperature and 29 microM at 35 degrees C. When a ventricular action potential waveform was used to elicit currents, the IC50 was 114 microM. Block of hERG by moxifloxacin was found to be voltage-dependent, occurred rapidly and was independent of stimulation frequency. Mutagenesis of the S6 helix residue Phe656 to Ala failed to eliminate or reduce the moxifloxacin-mediated block whereas mutation of Tyr652 to Ala reduced moxifloxacin block by approximately 66%. Our data demonstrate that moxifloxacin blocks the hERG channel with a preference for the activated channel state. The Tyr652 but not Phe656 S6 residue is involved in moxifloxacin block of hERG, concordant with an interaction in the channel inner cavity.[Alexandrou AJ et al; Br J Pharmacol 147 (8): 905-16 (2006)] Full text: PMC1760709","The bactericidal action of moxifloxacin results from inhibition of the topoisomerase II (DNA gyrase) and topoisomerase IV required for bacterial DNA replication, transcription, repair, and recombination. It appears that the C8-methoxy moiety contributes to enhanced activity and lower selection of resistant mutants of Gram-positive bacteria compared to the C8-H moiety. The presence of the bulky bicycloamine substituent at the C-7 position prevents active efflux, associated with the NorA or pmrA genes seen in certain Gram-positive bacteria.","Torsade de pointes (TdP) is increasingly recognized as a complication of drug therapy. The most common cause of drug-induced QT prolongation is inhibition of the rapidly activating component of the delayed potassium current (I(Kr)). Moxifloxacin, a widely used fluoroquinolone, is a weak I(Kr) inhibitor and has been associated with QT prolongation.","Fluoroquinolones prolong the QT interval by blocking voltage-gated potassium channels, especially the rapid component of the delayed rectifier potassium current I(Kr), expressed by HERG (the human ether-a-go-go-related gene). According to the available case reports and clinical studies, moxifloxacin carries the greatest risk of QT prolongation from all available quinolones in clinical practice and it should be used with caution in patients with predisposing factors for Torsades de pointes (TdP)."],"synonyms":["1-cyclopropyl--7-(2,8-diazabicyclo(4.3.0)non-8-yl)-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid","Actira","Avalox","Avelox","BAY 12-8039","BAY 128039","BAY-12-8039","BAY-128039","Izilox","moxifloxacin","moxifloxacin hydrochloride","Octegra","Proflox"],"pharmacology":["Moxifloxacin is a quinolone/fluoroquinolone antibiotic. Moxifloxacin can be used to treat infections caused by the following bacteria: Aerobic Gram-positive microorganisms: Corynebacterium species, Micrococcus luteus, Staphylococcus aureus, Staphylococcus epidermidis, Staphylococcus haemolyticus, Staphylococcus hominis, Staphylococcus warneri, Streptococcus pneumoniae, and Streptococcus viridans group. Aerobic Gram-negative microorganisms: Acinetobacter lwoffii, Haemophilus influenzae, and Haemophilus parainfluenzae. Other microorganisms: Chlamydia trachomatis.
Moxifloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase, which allows the untwisting required to replicate one DNA double helix into two. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian. Moxifloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria.","Moxifloxacin Base is a fluoroquinolone antibiotic with antibacterial activity. Moxifloxacin binds to and inhibits the bacterial enzymes DNA gyrase (topoisomerase II) and topoisomerase IV, resulting in inhibition of DNA replication and repair and cell death in sensitive bacterial species."],"description":["Moxifloxacin is a synthetic fluoroquinolone antibiotic agent. Bayer AG developed the drug (initially called BAY 12-8039) and it is marketed worldwide (as the hydrochloride) under the brand name Avelox (in some countries also Avalox) for oral treatment.","FDA Pharmacology Summary: Moxifloxacin is a Quinolone Antimicrobial. The chemical classification of moxifloxacin is Quinolones.","Metabolite Description: Moxifloxacin is only found in individuals that have used or taken this drug. It is a synthetic fluoroquinolone antibiotic agent. Bayer AG developed the drug (initially called BAY 12-8039) and it is marketed worldwide (as the hydrochloride) under the brand name Avelox (in some countries also Avalox) for oral treatment. The bactericidal action of moxifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV. DNA gyrase is an essential enzyme that is involved in the replication, transcription and repair of bacterial DNA. Topoisomerase IV is an enzyme known to play a key role in the partitioning of the chromosomal DNA during bacterial cell division.","LiverTox Summary: Moxifloxacin is a fourth generation fluoroquinolone with expanded activity against gram-positive bacteria as well as atypical pathogens. Moxifloxacin has been linked to mild ALT elevations during therapy and to rare instances of idiosyncratic acute liver injury with symptoms and jaundice.","Pharmacology: Moxifloxacin Base is a fluoroquinolone antibiotic with antibacterial activity. Moxifloxacin binds to and inhibits the bacterial enzymes DNA gyrase (topoisomerase II) and topoisomerase IV, resulting in inhibition of DNA replication and repair and cell death in sensitive bacterial species."],"atc_classification":["Antiinfectives for systemic use","Antibacterials for systemic use","Quinolone antibacterials","Fluoroquinolones","Moxifloxacin","Sensory organs","Ophthalmologicals","Antiinfectives","Fluoroquinolones","Moxifloxacin"],"_version_":1809284005082693600},{"antibiotic_name":"spectinomycin","canonical_smiles":"CC1CC(=O)C2(C(O1)OC3C(C(C(C(C3O2)NC)O)NC)O)O","cas_id":"1695-77-8","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"UNFWWIHTNXNPBV-WXKVUWSESA-N","isomeric_smiles":"C[C@@H]1CC(=O)[C@]2([C@@H](O1)O[C@@H]3[C@H]([C@@H]([C@@H]([C@@H]([C@H]3O2)NC)O)NC)O)O","molecular_formula":"C14H24N2O7","molecular_weight":"332.353 g/mol","pubchem_cid":"15541","pubchem_cid_i":15541,"mechanism_of_action":["Spectinomycin is an inhibitor of protein synthesis in the bacterial cell; the site of action is the 30S ribosomal subunit. It is bactericidal in its action."],"synonyms":["Actinospectacin","Adspec","Anhydrous Spectinomycin Dihydrochloride","Ferkel Spectam","Kempi","Prospec","Salmosan T","Salmosan-T","SalmosanT","Spectam","Spectam, Ferkel","Spectinomycin","Spectinomycin Dihydrochloride, Anhydrous","Spectinomycin Dihydrochloride, Pentahydrate","Spectinomycin Hydrochloride","Stanilo","Trobicin"],"pharmacology":["Spectinomycin is an aminocyclitol antibiotic produced by a species of soil microorganism designated as Streptomyces spectabilis. In vitro studies have shown spectinomycin to be active against most strains of Neisseria gonorrhoeae (minimum inhibitory concentration <7.5 to 20 mcg/mL). Footprint studies indicate that spectinomycin exerts regional effects on ribosomal structure.","Spectinomycin is an aminocyclitol aminoglycoside antibiotic derived from Streptomyces spectabilis with bacteriostatic activity. Spectinomycin binds to the bacterial 30S ribosomal subunit. As a result, this agent interferes with the initiation of protein synthesis and with proper protein elongation. This eventually leads to bacterial cell death."],"description":["An antibiotic produced by Streptomyces spectabilis. It is active against gram-negative bacteria and used for the treatment of gonorrhea.","Metabolite Description: Spectinomycin is only found in individuals that have used or taken this drug. It is an antibiotic produced by Streptomyces spectabilis. It is active against gram-negative bacteria and used for the treatment of gonorrhea. Spectinomycin is an inhibitor of protein synthesis in the bacterial cell; the site of action is the 30S ribosomal subunit. It is bactericidal in its action.","Pharmacology: Spectinomycin is an aminocyclitol aminoglycoside antibiotic derived from Streptomyces spectabilis with bacteriostatic activity. Spectinomycin binds to the bacterial 30S ribosomal subunit. As a result, this agent interferes with the initiation of protein synthesis and with proper protein elongation. This eventually leads to bacterial cell death.","An antibiotic produced by Streptomyces spectabilis. It is active against gram-negative bacteria and used for the treatment of gonorrhea."],"atc_classification":["Antiinfectives for systemic use","Antibacterials for systemic use","Other antibacterials","Other antibacterials","Spectinomycin"],"_version_":1809284005085839400},{"antibiotic_name":"tilmicosin","canonical_smiles":"CCC1C(C=C(C=CC(=O)C(CC(C(C(C(CC(=O)O1)O)C)OC2C(C(C(C(O2)C)O)N(C)C)O)CCN3CC(CC(C3)C)C)C)C)COC4C(C(C(C(O4)C)O)OC)OC","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"JTSDBFGMPLKDCD-NXYWBGGVSA-N","isomeric_smiles":"CC[C@H]1[C@H](/C=C(\\C=C\\C(=O)[C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)O)C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O)N(C)C)O)CCN3C[C@@H](C[C@@H](C3)C)C)C)/C)CO[C@H]4[C@@H]([C@@H]([C@@H]([C@H](O4)C)O)OC)OC","molecular_formula":"C46H80N2O13","molecular_weight":"869.147 g/mol","pubchem_cid":"16667713","pubchem_cid_i":16667713,"mechanism_of_action":["Tilmicosin has in vitro activity against gram-positive organisms and mycoplasma and is active against certain gram-negative organisms, such as Hemophilus somnus, Mannheimia (Pasteurella) hemolytica, and Pasteurella multocida. However, M. hemolytica is more sensitive than P. multocida to tilmicosin. Other gram-negative organisms tested, including Enterobacter aerogenes, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Salmonella, and Serratia species, are very resistant to tilmicosin. Some strains of Actinomyces also are extremely resistant to tilmicosin.","The antimicrobial mechanism seems to be the same for all of the macrolides. They interfere with protein synthesis by reversibly binding to the 50 S subunit of the ribosome. They appear to bind at the donor site, thus preventing the translocation necessary to keep the peptide chain growing. The effect is essentially confined to rapidly dividing bacteria and mycoplasmas. Macrolides are regarded as being bacteriostatic, ... . Macrolides are significantly more active at higher pH ranges (7.8-8). /Macrolides/","Macrolides have been reported to modify the host immune and inflammatory responses both in vivo and in vitro. /The authors/ examined the in vitro effect of the macrolides tilmicosin and tylosin, which are only used in the veterinary clinic, on the production of nitric oxide (NO), prostaglandin E2 (PGE2) and cytokines by lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages and mouse peripheral blood mononuclear cells (PBMCs). Compared with 5 ug/mL, tilmicosin and tylosin concentrations of 10 ug/mL and 20 ug/mL significantly decreased the production of 6-keto-prostaglandin F1alpha (6-keto-PGF1alpha), PGE2, NO, tumor necrosis factor-alpha (TNF-alpha), interleukin (IL)-1beta and IL-6, and increased IL-10 production. Cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) gene expression were also significantly reduced. These results support the opinion that macrolides may exert an anti-inflammatory effect through modulating the synthesis of several mediators and cytokines involved in the inflammatory process."],"synonyms":["20-deoxo-20-(3,5-dimethylpiperidin-1-yl)desmycosin","EL 870","EL-870","MICOTIL 300","tilmicosin"],"_version_":1809284005086888000},{"antibiotic_name":"dicloxacillin","canonical_smiles":"CC1=C(C(=NO1)C2=C(C=CC=C2Cl)Cl)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O","cas_id":"3116-76-5","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"YFAGHNZHGGCZAX-JKIFEVAISA-N","isomeric_smiles":"CC1=C(C(=NO1)C2=C(C=CC=C2Cl)Cl)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O","molecular_formula":"C19H17Cl2N3O5S","molecular_weight":"470.321 g/mol","pubchem_cid":"18381","pubchem_cid_i":18381,"pharmacological_classes":["Established Pharmacologic Class [EPC]: Penicillin-class Antibacterial","Chemical/Ingredient structural concept [Chemical/Ingredient]: Penicillins"],"mechanism_of_action":["ISOXAZOLYL PENICILLINS ARE POTENT INHIBITORS OF GROWTH OF MOST PENICILLINASE-PRODUCING STAPHYLOCOCCI. THIS IS THEIR VALID CLINICAL USE. DICLOXACILLIN...MORE POTENT THAT OXACILLIN & CLOXACILLIN... /ISOXAZOLYL PENICILLINS/","Dicloxacillin exerts a bactericidal action against penicillin-susceptible microorganisms during the state of active multiplication. All penicillins inhibit the biosynthesis of the bacterial cell wall. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, dicloxacillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that dicloxacillin interferes with an autolysin inhibitor."],"synonyms":["Alphapharm Brand of Dicloxacillin Sodium","Antibioticos Brand of Dicloxacillin Sodium","Bristol Myers Squibb Brand of Dicloxacillin Sodium","Bristol-Myers Squibb Brand of Dicloxacillin Sodium","Cilpen","Dichloroxacillin","Diclocil","Dicloxaciclin","Dicloxacillin","Dicloxacillin Sodium","Dicloxacillin, Monosodium Salt, Anhydrous","Dicloxacillin, Monosodium Salt, Mono-Hydrate","Dicloxacycline","Dicloxsig","Distaph","Ditterolina","Dycill","Dynapen","Fustery Brand of Dicloxacillin Sodium","Geneva Brand of Dicloxacillin Sodium","Infectopharm Brand of Dicloxacillin Sodium","InfectoStaph","Pathocil","Posipen","Sanfer Brand of Dicloxacillin Sodium","Sigma Brand of Dicloxacillin Sodium","SmithKline Beecham Brand of Dicloxacillin Sodium","Sodium, Dicloxacillin","Wyeth Brand of Dicloxacillin Sodium"],"pharmacology":["Dicloxacillin is a beta-lactamase resistant penicillin similar to oxacillin. Dicloxacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of dicloxacillin results from the inhibition of cell wall synthesis and is mediated through dicloxacillin binding to penicillin binding proteins (PBPs). Dicloxacillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.","Dicloxacillin is a broad-spectrum, semi-synthetic, beta-lactam, penicillin antibiotic with bactericidal and beta-lactamase resistant activity. Dicloxacillin binds to penicillin binding proteins (PBP) located on the inner membrane of the bacterial cell wall. It also inhibits the cross-linkage of peptidoglycan, a critical component of bacterial cell walls. This leads to the inhibition of bacterial cell wall synthesis and eventually causes cell lysis."],"description":["One of the penicillins which is resistant to penicillinase. [PubChem]","FDA Pharmacology Summary: Dicloxacillin is a Penicillin-class Antibacterial. The chemical classification of dicloxacillin is Penicillins.","LiverTox Summary: Dicloxacillin is an oral, second generation penicillin antibiotic that is used to treat bacterial infections caused by penicillinase-resistant staphylococci. Dicloxacillin has been linked to rare instances of clinically apparent, idiosyncratic liver injury.","Metabolite Description: Dicloxacillin is only found in individuals that have used or taken this drug. It is one of the penicillins which is resistant to penicillinase. [PubChem]Dicloxacillin exerts a bactericidal action against penicillin-susceptible microorganisms during the state of active multiplication. All penicillins inhibit the biosynthesis of the bacterial cell wall. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, dicloxacillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that dicloxacillin interferes with an autolysin inhibitor.","Pharmacology: Dicloxacillin is a broad-spectrum, semi-synthetic, beta-lactam, penicillin antibiotic with bactericidal and beta-lactamase resistant activity. Dicloxacillin binds to penicillin binding proteins (PBP) located on the inner membrane of the bacterial cell wall. It also inhibits the cross-linkage of peptidoglycan, a critical component of bacterial cell walls. This leads to the inhibition of bacterial cell wall synthesis and eventually causes cell lysis.","One of the PENICILLINS which is resistant to PENICILLINASE."],"atc_classification":["Antiinfectives for systemic use","Antibacterials for systemic use","Beta-lactam antibacterials, penicillins","Beta-lactamase resistant penicillins","Dicloxacillin"],"_version_":1809284005088985000},{"antibiotic_name":"streptomycin","canonical_smiles":"CC1C(C(C(O1)OC2C(C(C(C(C2O)O)N=C(N)N)O)N=C(N)N)OC3C(C(C(C(O3)CO)O)O)NC)(C=O)O","cas_id":"57-92-1","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"UCSJYZPVAKXKNQ-HZYVHMACSA-N","isomeric_smiles":"C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)N=C(N)N)O)N=C(N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)NC)(C=O)O","molecular_formula":"C21H39N7O12","molecular_weight":"581.58 g/mol","pubchem_cid":"19649","pubchem_cid_i":19649,"pharmacological_classes":["Established Pharmacologic Class [EPC]: Aminoglycoside Antibacterial","Chemical/Ingredient structural concept [Chemical/Ingredient]: Aminoglycosides","Established Pharmacologic Class [EPC]: Antimycobacterial"],"mechanism_of_action":["The primary intracellular site of action of the aminoglycosides is the 30 S ribosomal subunit, which consists of 21 proteins and a single 16 S molecule of RNA. at least three of these proteins and perhaps the 16 S ribosomal RNA as well contribute to the streptomycin binding site, and alterations of these molecules markedly affect the binding and subsequent action of streptomycin. For example, a single amino acid substitution of asparagine for lysine at position 42 of one ribosomal protein (S12) prevents binding of the drug; the resultant mutant is totally resistant to streptomycin. Another mutant, in which glutamine is the amino acid at this position, is dependent on streptomycin.","STREPTOMYCIN DEPRESSED NEUROMUSCULAR TRANSMISSION IN THE RAT SCIATIC NERVE GASTROCNEMIUS MUSCLE PREPN, BUT DID NOT DEPRESS THE DIRECTLY-EVOKED TWITCH IN CHRONICALLY DENERVATED GASTROCNEMIUS MUSCLE. IN THE ISOLATED SCIATIC NERVE, STREPTOMYCIN DECR THE AMPLITUDE OF ACTION POTENTIALS. STREPTOMYCIN ALSO SUPPRESSED POST-TETANIC POTENTIATION IN THE NERVE-MUSCLE PREPN. STREPTOMYCIN INHIBITED MUSCLE CONTRACTION INDUCED BY ACETYLCHOLINE. THUS, STREPTOMYCIN MAY INHIBIT NEUROMUSCULAR TRANSMISSION BY COMPETING WITH ACETYLCHOLINE FOR CHOLINERGIC RECEPTOR SITES, BY DECREASING ENDPLATE SENSITIVITY, OR BY A PRESYNAPTIC ACTION BY INTERACTING WITH CALCIUM.","Streptomycin has a neuromuscular blocking effect and decreases indirectly stimulated contractions of the gastrocnemius muscle in anaesthetized piglets and lambs ... .","Aminoglycosides like Streptomycin \"irreversibly\" bind to specific 30S-subunit proteins and 16S rRNA. Specifically Streptomycin binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes."],"synonyms":["Estreptomicina CEPA","Estreptomicina Clariana","Estreptomicina Normon","Strepto Fatol","Strepto Hefa","Strepto-Fatol","Strepto-Hefa","Streptomycin","Streptomycin Grünenthal","Streptomycin Sulfate","Streptomycin Sulfate (2:3) Salt","Streptomycin Sulphate","Streptomycine Panpharma"],"pharmacology":["Streptomycin is an aminoglycoside antibiotic. Aminoglycosides work by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA, leaving the bacterium unable to synthesize proteins vital to its growth. Aminoglycosides are useful primarily in infections involving aerobic, Gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter. In addition, some mycobacteria, including the bacteria that cause tuberculosis, are susceptible to aminoglycosides. Infections caused by Gram-positive bacteria can also be treated with aminoglycosides, but other types of antibiotics are more potent and less damaging to the host. In the past the aminoglycosides have been used in conjunction with penicillin-related antibiotics in streptococcal infections for their synergistic effects, particularly in endocarditis. Aminoglycosides are mostly ineffective against anaerobic bacteria, fungi and viruses.","Streptomycin is an aminoglycoside antibiotic derived from Streptomyces griseus with antibacterial activity. Streptomycin irreversibly binds to the 16S rRNA and S12 protein within the bacterial 30S ribosomal subunit. As a result, this agent interferes with the assembly of initiation complex between mRNA and the bacterial ribosome, thereby inhibiting the initiation of protein synthesis. In addition, streptomycin induces misreading of the mRNA template and causes translational frameshift, thereby results in premature termination. This eventually leads to bacterial cell death."],"description":["Streptomycin is an aminoglycoside antibiotic produced by the soil actinomycete Streptomyces griseus. It acts by binding to the 30S ribosomal subunit of susceptible organisms and disrupting the initiation and elongation steps in protein synthesis. It is bactericidal due to effects that are not fully understood.","FDA Pharmacology Summary: Streptomycin is an Aminoglycoside Antibacterial and Antimycobacterial. The chemical classification of streptomycin is Aminoglycosides.","Physical Description: Streptomycin sulfate (2:3) (salt) is an antibacterial. White to light gray or pale buff powder with faint amine-like odor.","LiverTox Summary: Streptomycin is a broad spectrum aminoglycoside antibiotic typically used for treatment of active tuberculosis, always in combination with other antituberculosis agents. Streptomycin is usually used in combination with agents that are known to be hepatotoxic and the role of streptomycin in liver injury has been difficult to assess, but most information suggests that streptomycin is not hepatotoxic.","Metabolite Description: Streptomycin is an aminoglycoside antibiotic produced by the soil actinomycete Streptomyces griseus. It acts by binding to the 30S ribosomal subunit of susceptible organisms and disrupting the initiation and elongation steps in protein synthesis. It is bactericidal due to effects that are not fully understood.","Pharmacology: Streptomycin is an aminoglycoside antibiotic derived from Streptomyces griseus with antibacterial activity. Streptomycin irreversibly binds to the 16S rRNA and S12 protein within the bacterial 30S ribosomal subunit. As a result, this agent interferes with the assembly of initiation complex between mRNA and the bacterial ribosome, thereby inhibiting the initiation of protein synthesis. In addition, streptomycin induces misreading of the mRNA template and causes translational frameshift, thereby results in premature termination. This eventually leads to bacterial cell death.","An antibiotic produced by the soil actinomycete Streptomyces griseus. It acts by inhibiting the initiation and elongation processes during protein synthesis."],"atc_classification":["Alimentary tract and metabolism","Antidiarrheals, intestinal antiinflammatory/antiinfective agents","Intestinal antiinfectives","Antibiotics","Streptomycin","Antiinfectives for systemic use","Antibacterials for systemic use","Aminoglycoside antibacterials","Streptomycins","Streptomycin"],"_version_":1809284005091082200},{"antibiotic_name":"daptomycin","canonical_smiles":"CCCCCCCCCC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CC(=O)N)C(=O)NC(CC(=O)O)C(=O)NC3C(OC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC3=O)CCCN)CC(=O)O)C)CC(=O)O)CO)C(C)CC(=O)O)CC(=O)C4=CC=CC=C4N)C","cas_id":"103060-53-3","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"DOAKLVKFURWEDJ-QCMAZARJSA-N","isomeric_smiles":"CCCCCCCCCC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@H](CC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H]3[C@H](OC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC3=O)CCCN)CC(=O)O)C)CC(=O)O)CO)[C@H](C)CC(=O)O)CC(=O)C4=CC=CC=C4N)C","molecular_formula":"C72H101N17O26","molecular_weight":"1620.693 g/mol","pubchem_cid":"21585658","pubchem_cid_i":21585658,"pharmacological_classes":["Established Pharmacologic Class [EPC]: Lipopeptide Antibacterial","Chemical/Ingredient structural concept [Chemical/Ingredient]: Lipopeptides"],"mechanism_of_action":["Daptomycin appears to bind or insert into the outer membrane of gram positive bacteria. The binding and integration of daptomycin into the cell membrane is calcium dependent. Calcium ions cause a conformational change in daptomycin, augmenting its amphipathicity (hydrophilic head group and hydrophobic tail group), leading to incorporation into the cell membrane. This binding causes rapid depolarisation, resulting in a loss of membrane potential leading to inhibition of protein, DNA and RNA synthesis, which results in bacterial cell death. The bactericidal activity of daptomycin is concentration-dependent. There is in vitro evidence of synergy with ?-lactam antibiotics."],"synonyms":["Cubicin","Daptomycin","Daptomycin, 9 L beta Aspartic Acid","Daptomycin, 9-L beta-Aspartic Acid","Deptomycin","LY 146032","LY-146032","LY146032"],"pharmacology":["Daptomycin is a 13 member amino acid cyclic lipopeptide antibiotic active against Gram-positive bacteria only. It has proven in vitro activity against enterococci (including glycopeptide-resistant Enterococci (GRE)), staphylococci (including methicillin-resistant Staphylococcus aureus), streptococci and corynebacteria. Daptomycin is derived from the fermentation product of Streptomyces roseosporus.","Daptomycin is a semi-synthetic cyclic lipopeptide antibiotic isolated form the bacterium Streptomyces roseosporus with broad-spectrum antibiotic activity against Gram-positive bacteria. Daptomycin has a distinct mechanism of action, in which it binds to bacterial membrane and causes rapid depolarization of the cell membrane due to calcium-dependant potassium efflux; the loss of membrane potential leads to inhibition of DNA, RNA and protein synthesis, resulting in bacterial cell death. This agent does not penetrate the outer membrane of gram-negative bacteria."],"description":["Daptomycin is a lipopeptide antibiotic that kills susceptible gram positive bacteria by disrupting their membrane potential. It is a naturally-occurring compound found in the soil bacterium Streptomyces roseosporus. Antibiotics are used in the treatment of infections caused by bacteria. They work by killing bacteria or preventing their growth. Daptomycin will not work for colds, flu, or other virus infections. It was approved in September 2003 for the treatment of complicated skin and soft tissue infections. It has a safety profile similar to other agents commonly administered to treat gram-positive infections.","FDA Pharmacology Summary: Daptomycin is a Lipopeptide Antibacterial. The chemical classification of daptomycin is Lipopeptides.","LiverTox Summary: Daptomycin is an intravenously administered, broad spectrum antibiotic used to treat complex skin and tissue infections, endocarditis and bacteremia. Daptomycin is associated with a low to modest rate of serum enzyme elevations during therapy, but is a very rare cause of clinically apparent liver injury.","Pharmacology: Daptomycin is a semi-synthetic cyclic lipopeptide antibiotic isolated form the bacterium Streptomyces roseosporus with broad-spectrum antibiotic activity against Gram-positive bacteria. Daptomycin has a distinct mechanism of action, in which it binds to bacterial membrane and causes rapid depolarization of the cell membrane due to calcium-dependant potassium efflux; the loss of membrane potential leads to inhibition of DNA, RNA and protein synthesis, resulting in bacterial cell death. This agent does not penetrate the outer membrane of gram-negative bacteria.","A cyclic lipopeptide antibiotic that inhibits GRAM-POSITIVE BACTERIA."],"atc_classification":["Antiinfectives for systemic use","Antibacterials for systemic use","Other antibacterials","Other antibacterials","Daptomycin"],"_version_":1809284005093179400},{"antibiotic_name":"amoxicillin/clavulanic acid","canonical_smiles":"CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)C(=O)O)C.C1C2N(C1=O)C(C(=CCO)O2)C(=O)[O-].[K+]","cas_id":"74469-00-4","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"DWHGNUUWCJZQHO-ZVDZYBSKSA-M","isomeric_smiles":"CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)N)C(=O)O)C.C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)[O-].[K+]","molecular_formula":"C24H27KN4O10S","molecular_weight":"602.656 g/mol","pubchem_cid":"23665637","pubchem_cid_i":23665637,"synonyms":["Amox clav","Amox-clav","Amoxi Clavulanate","Amoxi-Clavulanate","Amoxicillin Clavulanic Acid","Amoxicillin Potassium Clavulanate Combination","Amoxicillin-Clavulanic Acid","Amoxicillin-Potassium Clavulanate Combination","Amoxycillin Clavulanic Acid","Amoxycillin, Clavulanate Potentiated","Amoxycillin-Clavulanic Acid","Augmentin","BRL 25000","BRL-25000","BRL25000","Clavulanate Potentiated Amoxycillin","Clavulanate-Amoxicillin Combination, Potassium","Clavulin","Co amoxiclav","Co-amoxiclav","Coamoxiclav","Combination, Potassium Clavulanate-Amoxicillin","Potassium Clavulanate Amoxicillin Combination","Potassium Clavulanate-Amoxicillin Combination","Potentiated Amoxycillin, Clavulanate","Spektramox","Synulox"],"description":["A fixed-ratio combination of amoxicillin trihydrate and potassium clavulanate."],"_version_":1809284005094228000},{"antibiotic_name":"quinupristin/dalfopristin","canonical_smiles":"CCC1C(=O)N2CCCC2C(=O)N(C(C(=O)N3CC(C(=O)CC3C(=O)NC(C(=O)OC(C(C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CSC6CN7CCC6CC7)CC8=CC=C(C=C8)N(C)C)C.CCN(CC)CCS(=O)(=O)C1CCN2C1C(=O)OC(C(C=CC(=O)NCC=CC(=CC(CC(=O)CC3=NC(=CO3)C2=O)O)C)C)C(C)C","date_inserted":"2019-04-24T15:29:45.812Z","date_modified":"2019-04-24T15:29:45.812Z","inchi_key":"PPKJUHVNTMYXOD-HVWWIRKTSA-N","isomeric_smiles":"CC[C@@H]1C(=O)N2CCC[C@H]2C(=O)N([C@H](C(=O)N3CC(C(=O)CC3C(=O)N[C@H](C(=O)O[C@@H]([C@@H](C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CS[C@@H]6CN7CCC6CC7)CC8=CC=C(C=C8)N(C)C)C.CCN(CC)CCS(=O)(=O)[C@@H]1CCN2C1C(=O)O[C@@H]([C@@H](/C=C/C(=O)NC/C=C/C(=C/[C@H](CC(=O)CC3=NC(=CO3)C2=O)O)/C)C)C(C)C","molecular_formula":"C87H117N13O19S2","molecular_weight":"1713.085 g/mol","pubchem_cid":"23724510","pubchem_cid_i":23724510,"synonyms":["quinupristin-dalfopristin","RP 59500","RP-59500","Synercid"],"description":["LiverTox Summary: Quinupristin and dalfopristin are intravenously administered, streptogramin antibiotics used in fixed combination to treat severe bacterial infections due to susceptible organisms including methicillin resistant Staphylococcus aureus (MRSA). The fixed combination of quinupristin and dalfopristin is associated with a low rate of serum enzyme elevations during therapy but has not been convincingly linked to instances of clinically apparent liver injury."],"_version_":1809284005095276500}]