Compound ID | 1913

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Ceftibuten

Class: Beta-lactam (cephalosporin, third generation)

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 against many Enterobacteriaceae but vulnerable to extended-spectum beta-lactamases (ESBL)
Description: Semisynthetic Cephalosporine, derived from Cephalosporin C. Oral application. Fixed combination with the beta-lactamase inhibitor VNRX-7145 (Ledaborbactam etzadroxil) in clinical development
Year first mentioned: 1987
Highest developmental phase: Approved by FDA in 1995
Development status: Discontinued
Chemical structure(s):
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Molecular weight: 410.43
Iso. SMILES: C1C=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)/C(=C\CC(=O)O)/C3=CSC(=N3)N)C(=O)O
InChI Key: UNJFKXSSGBWRBZ-BJCIPQKHSA-N
Can. SMILES: C(=C(\C1=CSC(=N1)N)/C(=O)N[C@@H]2C(=O)N3C(=CCS[C@H]23)C(=O)O)/CC(=O)O
InChI: InChI=1S/C15H14N4O6S2/c16-15-17-7(5-27-15)6(1-2-9(20)21)11(22)18-10-12(23)19-8(14(24)25)3-4-26-13(10)19/h1,3,5,10,13H,2,4H2,(H2,16,17)(H,18,22)(H,20,21)(H,24,25)/b6-1-/t10-,13-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5282242
Guide to Pharmacology: ceftibuten
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7922365/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8865001/
  • https://pubmed.ncbi.nlm.nih.gov/9250548/

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