Compound ID | 1945

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Carfecillin

Class: Beta-lactam (carboxypenicillin)

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 and some Gram-negative bacteria including Pseudomonas aeruginosa, but vulnerable to beta-lactamases
Description: Semisynthetic penicillin, derived from 6-aminopenicillanic acid (6-APA). Oral prodrug of carbenicillin (Carbenicillin phenyl ester). Used for urinary tract infections.
Year first mentioned: 1974
Development status: Unknown
Chemical structure(s):
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Molecular weight: 454.5
Iso. SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C(C3=CC=CC=C3)C(=O)OC4=CC=CC=C4)C(=O)O)C
InChI Key: NZDASSHFKWDBBU-KVMCETHSSA-N
Can. SMILES: CC1(C)[C@H](C(=O)O)N2C(=O)[C@H]([C@H]2S1)NC(=O)C(C3=CC=CC=C3)C(=O)OC4=CC=CC=C4
InChI: InChI=1S/C23H22N2O6S/c1-23(2)17(21(28)29)25-19(27)16(20(25)32-23)24-18(26)15(13-9-5-3-6-10-13)22(30)31-14-11-7-4-8-12-14/h3-12,15-17,20H,1-2H3,(H,24,26)(H,28,29)/t15?,16-,17+,20-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/33672
Guide to Pharmacology: carfecillin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/21771/
  • https://academic.oup.com/jac/article-abstract/2/2/175/753476

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