Compound ID | 1907

Cefixime

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
Year first mentioned: 1984
Development status: Approved, off-patent
Chemical structure(s):
Canonical SMILES: C=CC1=C(C(=O)O)N2C(=O)[C@H]([C@H]2SC1)NC(=O)/C(=N\OCC(=O)O)/C3=CSC(=N3)N
Isomeric SMILES: C=CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OCC(=O)O)/C3=CSC(=N3)N)SC1)C(=O)O
InChI: InChI=1S/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/b20-9-/t10-,14-/m1/s1
InChI Key: OKBVVJOGVLARMR-QSWIMTSFSA-N
Structure link: https://pubchem.ncbi.nlm.nih.gov/compound/5362065
External links:
Guide to Pharmacology: cefixime
Main Source: https://pubmed.ncbi.nlm.nih.gov/11330356/
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3909252/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6124830/
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