Compound ID | 1908

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Cefmenoxime

Synonym(s): Bestron  |  Cefmax  |  SCE-1365

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. Available for ocular application in some countries.
Institute where first reported: Tap Pharmaceuticals
Year first mentioned: 1980
Highest developmental phase: Approved by FDA in 1987
Development status: Approved
Reason Dropped: Discontinued in the US
Chemical structure(s):
Click here for structure editor
Molecular weight: 511.56
Iso. SMILES: CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)/C(=N\OC)/C4=CSC(=N4)N)SC2)C(=O)O
InChI Key: HJJDBAOLQAWBMH-YCRCPZNHSA-N
Can. SMILES: CN1C(=NN=N1)SCC2=C(C(=O)O)N3C(=O)[C@H]([C@H]3SC2)NC(=O)/C(=N\OC)/C4=CSC(=N4)N
InChI: InChI=1S/C16H17N9O5S3/c1-24-16(20-22-23-24)33-4-6-3-31-13-9(12(27)25(13)10(6)14(28)29)19-11(26)8(21-30-2)7-5-32-15(17)18-7/h5,9,13H,3-4H2,1-2H3,(H2,17,18)(H,19,26)(H,28,29)/b21-8-/t9-,13-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/9570757
Guide to Pharmacology: cefmenoxime
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8779982/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC181357/

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