Compound ID | 1919

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Cefepime

Synonym(s): BMY-28142

Class: Beta-lactam (cephalosporin, fourth 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-negative bacteria but vulnerable to higher levels of extended-spectum beta-lactamases (ESBL) and high resistance rates in Pseudomonas aeruginosa
Description: Semisynthetic Cephalosporine, derived from Cephalosporin C. Fixed combination with several beta-lactamase inhibitors (taniborbactam, zidebactam, enmetazobactam, tazobactam)
Year first mentioned: 1982
Highest developmental phase: Approved by FDA in 1996
Development status: Approved
Chemical structure(s):
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Molecular weight: 480.56
Iso. SMILES: C[N+]1(CCCC1)CC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)/C(=N\OC)/C4=CSC(=N4)N)SC2)C(=O)[O-]
InChI Key: HVFLCNVBZFFHBT-ZKDACBOMSA-N
Can. SMILES: C[N+]1(CCCC1)CC2=C(C(=O)[O-])N3C(=O)[C@H]([C@H]3SC2)NC(=O)/C(=N\OC)/C4=CSC(=N4)N
InChI: InChI=1S/C19H24N6O5S2/c1-25(5-3-4-6-25)7-10-8-31-17-13(16(27)24(17)14(10)18(28)29)22-15(26)12(23-30-2)11-9-32-19(20)21-11/h9,13,17H,3-8H2,1-2H3,(H3-,20,21,22,26,28,29)/b23-12-/t13-,17-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5479537
Guide to Pharmacology: cefepime
Citations:
  • https://linkinghub.elsevier.com/retrieve/pii/S1473309907701093
  • https://pubmed.ncbi.nlm.nih.gov/29166830/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8502754/
  • https://pubmed.ncbi.nlm.nih.gov/8150771/

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