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:	Approved, off-patent, not available in most countries

Chemical structure(s):
Canonical 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
Isomeric 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:	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
InChI Key:	NZDASSHFKWDBBU-KVMCETHSSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/33672

External links:
Guide to Pharmacology:	carfecillin
Main Source:	https://academic.oup.com/jac/article-abstract/2/2/175/753476
Citation:	https://pubmed.ncbi.nlm.nih.gov/21771/