Compound ID | 1925

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Ampicillin

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). Oral (bacampicillin, pivampicillin) and parenteral application. Fixed combination with sulbactam available.
Institute where first reported: Sandoz
Year first mentioned: 1953
Highest development stage: Approved by FDA in 1971
Development status: Approved, off-patent
Chemical structure(s):
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Molecular weight: 349.41
Iso. SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)C
InChI Key: AVKUERGKIZMTKX-NJBDSQKTSA-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
InChI: InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6249
Guide to Pharmacology: ampicillin
Citations:
  • https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1742-1241.1962.tb06419.x
  • https://bpspubs.onlinelibrary.wiley.com/doi/abs/10.1111/j.1476-5381.1962.tb01416.x?sid=nlm%3Apubmed
  • https://pmc.ncbi.nlm.nih.gov/articles/PMC1243665/
  • https://www.nature.com/articles/183257b0

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