Compound ID | 1891

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Cefmetazole

Class: Beta-lactam (cephalosporin, second 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; less vulnerable to extended-spectum beta-lactamases (ESBL)
Description: Semisynthetic Cephalosporin (cephamycin), derived from Cephalosporin C
Year first mentioned: 1979
Highest developmental phase: Approved by FDA in 1989
Development status: Discontinued
Chemical structure(s):
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Molecular weight: 471.54
Iso. SMILES: CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@](C3=O)(NC(=O)CSCC#N)OC)SC2)C(=O)O
InChI Key: SNBUBQHDYVFSQF-HIFRSBDPSA-N
Can. SMILES: CN1C(=NN=N1)SCC2=C(C(=O)O)N3C(=O)[C@]([C@H]3SC2)(NC(=O)CSCC#N)OC
InChI: InChI=1S/C15H17N7O5S3/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/t13-,15+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/42008
Guide to Pharmacology: cefmetazole
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/2020609/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4991070/
  • https://pubmed.ncbi.nlm.nih.gov/2692950/

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