Compound ID | 1909

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Cefoperazone

Synonym(s): Sulperazon (sulbactam sodium/cefoperazone sodium)

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 some Enterobacteriaceae and Pseudomonas aeruginosa but high resistance rates
Description: Semisynthetic Cephalosporine, derived from Cephalosporin C. Fixed combination with sulbactam available in some countries
Institute where first reported: Pfizer
Year first mentioned: 1974
Highest developmental phase: Approved by FDA in 1982
Development status: Approved (only in combination with sulbactam)
Reason Dropped: Discontinued in US
Chemical structure(s):
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Molecular weight: 645.67
Iso. SMILES: CCN1CCN(C(=O)C1=O)C(=O)N[C@H](C2=CC=C(C=C2)O)C(=O)N[C@H]3[C@@H]4N(C3=O)C(=C(CS4)CSC5=NN=NN5C)C(=O)O
InChI Key: GCFBRXLSHGKWDP-XCGNWRKASA-N
Can. SMILES: CCN1CCN(C(=O)C1=O)C(=O)N[C@H](C2=CC=C(C=C2)O)C(=O)N[C@@H]3C(=O)N4C(=C(CS[C@H]34)CSC5=NN=NN5C)C(=O)O
InChI: InChI=1S/C25H27N9O8S2/c1-3-32-8-9-33(21(39)20(32)38)24(42)27-15(12-4-6-14(35)7-5-12)18(36)26-16-19(37)34-17(23(40)41)13(10-43-22(16)34)11-44-25-28-29-30-31(25)2/h4-7,15-16,22,35H,3,8-11H2,1-2H3,(H,26,36)(H,27,42)(H,40,41)/t15-,16-,22-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/44187
Guide to Pharmacology: cefoperazone
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4990596/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6304247/
  • https://pubmed.ncbi.nlm.nih.gov/32129861/

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