Compound ID | 3678

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Ceftizoxime

Synonym(s): Ceftizoxima  |  Ceftizoximum  |  Cefizox  |  FK-749  |  FK749  |  Epocelin

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Cell wall synthesis inhibitor. Binds penicillin-binding proteins and inhibits the final transpeptidation step of peptidoglycan synthesis, thereby inhibiting bacterial cell-wall formation.
Target Pathogen: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pneumoniae, Streptococcus pyogenes, Streptococcus agalactiae, Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Enterobacter aerogenes, Citrobacter freundii, Serratia marcescens, Proteus mirabilis, Proteus vulgaris, Morganella morganii, Providencia rettgeri, Haemophilus influenzae, Neisseria gonorrhoeae, Acinetobacter calcoaceticus, Pseudomonas aeruginosa
Description: Semisynthetic third-generation cephalosporin antibacterial that inhibits bacterial cell-wall synthesis; approved in Japan in 1982 and by the US FDA in 1983.
Institute where first reported: Fujisawa Pharmaceutical Co., Ltd., Japan
Year first mentioned: 1978
Highest development stage: Approved
Development status: Approved
Chemical structure(s):
Click here for structure editor
Molecular weight:
Iso. SMILES: CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=CCS3)C(=O)O
InChI Key: NNULBSISHYWZJU-LLKWHZGFSA-N
Can. SMILES: CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@@H]2C(=O)N3C(=CCS[C@H]23)C(=O)O
InChI: InChI=1S/C13H13N5O5S2/c1-23-17-7(5-4-25-13(14)15-5)9(19)16-8-10(20)18-6(12(21)22)2-3-24-11(8)18/h2,4,8,11H,3H2,1H3,(H2,14,15)(H,16,19)(H,21,22)/b17-7-/t8-,11-/m1/s1
External links:
Structure link: https://pubchem.ncbi.nlm.nih.gov/compound/6533629
Guide to Pharmacology: ceftizoxime
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/525994/
  • https://journals.asm.org/doi/10.1128/aac.17.4.583
  • https://doi.org/10.7164/antibiotics.32.1319
    • Patents:
  • JPS53137988A
  • GB1600735A
  • US4425341A
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