Carindacillin

Synonym(s): Indanyl carbenicillin

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. Used for urinary tract infections.
Year first mentioned:	1972
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=C5CCCC5=C4
Isomeric SMILES:	CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C(C3=CC=CC=C3)C(=O)OC4=CC5=C(CCC5)C=C4)C(=O)O)C
InChI:	InChI=1S/C26H26N2O6S/c1-26(2)20(24(31)32)28-22(30)19(23(28)35-26)27-21(29)18(15-7-4-3-5-8-15)25(33)34-17-12-11-14-9-6-10-16(14)13-17/h3-5,7-8,11-13,18-20,23H,6,9-10H2,1-2H3,(H,27,29)(H,31,32)/t18?,19-,20+,23-/m1/s1
InChI Key:	JIRBAUWICKGBFE-MNRDOXJOSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/Carbenicillin-indanyl

External links:
Guide to Pharmacology:	carindacillin
Main Source:	https://pubmed.ncbi.nlm.nih.gov/577917/
Citations:	https://journals.asm.org/doi/pdf/10.1128/AAC.1.3.185 https://pubmed.ncbi.nlm.nih.gov/10454465/