Compound ID | 1928

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Cloxacillin

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Cell wall synthesis inhibitor. Binds to bacterial penicillin-binding proteins (PBP); PBP inhibitor
Target Pathogen: Active against Gram-positive bacteria, especially staphylococci including penicillinase producing strains
Description: Semisynthetic penicillin, derived from 6-aminopenicillanic acid (6-APA); parenteral application; an isoxazolylpenicillin-type
Year first mentioned: 1963
Highest development stage: Approved by FDA in 1971
Development status: Approved
Reason dropped: Discontinued/Withdrawn in many countries
Chemical structure(s):
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Molecular weight: 435.88
Iso. SMILES: CC1=C(C(=NO1)C2=CC=CC=C2Cl)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
InChI Key: LQOLIRLGBULYKD-JKIFEVAISA-N
Can. SMILES: CC1=C(C(=NO1)C2=C(C=CC=C2)Cl)C(=O)N[C@@H]3C(=O)N4[C@@H](C(=O)O)C(C)(C)S[C@H]34
InChI: InChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6098
Guide to Pharmacology: cloxacillin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/22542764/
  • https://pubmed.ncbi.nlm.nih.gov/4919148/

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