Compound ID | 1933

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Methicillin

Synonym(s): Meticillin

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
Year first mentioned: 1960
Highest development stage: Approved by FDA in 1971
Development status: Withdrawn
Reason dropped: Due to associated side effects
Chemical structure(s):
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Molecular weight: 380.42
Iso. SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C3=C(C=CC=C3OC)OC)C(=O)O)C
InChI Key: RJQXTJLFIWVMTO-TYNCELHUSA-N
Can. SMILES: CC1(C)[C@H](C(=O)O)N2C(=O)[C@H]([C@H]2S1)NC(=O)C3=C(C=CC=C3OC)OC
InChI: InChI=1S/C17H20N2O6S/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23)/t11-,12+,15-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6087
Guide to Pharmacology: methicillin
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC124322/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6939889/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1482072/

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