Compound ID | 1940

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Metampicillin

Synonym(s): Methylenampicillin

Class: Beta-lactam (aminopenicillin)

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Binds to bacterial penicillin-binding proteins (PBP) and interferes with bacterial cell wall integrity and synthesis. Active against Gram-positive bacteria and some Enterobacteriaceae, but vulnerable to penicillinases produced by staphylococci and E. coli
Description: Prodrug of ampicillin
Year first mentioned: 1969
Highest developmental phase: Approved
Development status: Approved
Chemical structure(s):
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Molecular weight: 361.42
Iso. SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N=C)C(=O)O)C
InChI Key: FZECHKJQHUVANE-MCYUEQNJSA-N
Can. SMILES: CC1(C)[C@H](C(=O)O)N2C(=O)[C@H]([C@H]2S1)NC(=O)[C@@H](C3=CC=CC=C3)N=C
InChI: InChI=1S/C17H19N3O4S/c1-17(2)12(16(23)24)20-14(22)11(15(20)25-17)19-13(21)10(18-3)9-7-5-4-6-8-9/h4-8,10-12,15H,3H2,1-2H3,(H,19,21)(H,23,24)/t10-,11-,12+,15-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6713928
Guide to Pharmacology: metampicillin
Citations:
  • https://www.nature.com/articles/s41598-020-74990-1
  • https://doi.org/10.1159/000220849
  • https://doi.org/10.1159/000220849

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