Compound ID | 1951

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Bacampicillin

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: Semisynthetic penicillin, derived from 6-aminopenicillanic acid (6-APA), ampicillin-ester. Oral application
Institute where first reported: Pfizer
Year first mentioned: 1975
Highest developmental phase: Approved by FDA in 1980
Development status: Discontinued
Chemical structure(s):
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Molecular weight: 465.52
Iso. SMILES: CCOC(=O)OC(C)OC(=O)[C@H]1C(S[C@H]2N1C(=O)[C@H]2NC(=O)[C@@H](C3=CC=CC=C3)N)(C)C
InChI Key: PFOLLRNADZZWEX-FFGRCDKISA-N
Can. SMILES: CCOC(=O)OC(C)OC(=O)[C@H]1C(C)(C)S[C@@H]2[C@@H](C(=O)N12)NC(=O)[C@@H](C3=CC=CC=C3)N
InChI: InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/441397
Guide to Pharmacology: bacampicillin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/6762528/
  • https://pubmed.ncbi.nlm.nih.gov/1211909/

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