Compound ID | 1944

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Carindacillin

Synonym(s): Indanyl carbenicillin  |  Carbenicillin indanyl

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
Highest developmental phase: Approved by FDA in 1972
Development status: Discontinued
Chemical structure(s):
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Molecular weight: 494.56
Iso. 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 Key: JIRBAUWICKGBFE-MNRDOXJOSA-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=C5CCCC5=C4
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/Carbenicillin-indanyl
Guide to Pharmacology: carindacillin
Citations:
  • https://journals.asm.org/doi/pdf/10.1128/AAC.1.3.185
  • https://pubmed.ncbi.nlm.nih.gov/10454465/
  • https://pubmed.ncbi.nlm.nih.gov/577917/

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