Structure via PubChem · Public domain (PubChem)
cefoperazone
Sign in to saveAlso known as CPZ, (6R,7R)-7-({(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl}amino)-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cefoperazone is a third-generation cephalosporin antibiotic, marketed by Pfizer under the name Cefobid. It is one of few cephalosporin antibiotics effective in treating Pseudomonas bacterial infections which are otherwise resistant to these antibiotics.
Chemical data
- Formula
- C25H27N9O8S2
- Molecular weight
- 645.7 g/mol
- IUPAC name
- (6R,7R)-7-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- 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
- InChIKey
- GCFBRXLSHGKWDP-XCGNWRKASA-N
- XLogP
- -0.7
- Polar surface area
- 271 Ų
- H-bond donors
- 4
- H-bond acceptors
- 13
- Formal charge
- 0
via PubChem
Research
3,428 papers- Cefoperazone/sulbactam: New composites against multiresistant gram negative bacteria?Infection, genetics and evolution : journal of molecular epidemiology and evolutionary genetics in infectious diseases · 2021
- Cefoperazone/sulbactam-induced hemolytic anemia.Journal of postgraduate medicine · 2023
- Cefoperazone (Cefobid, Pfizer).Drug intelligence & clinical pharmacy · 1983
- Cefoperazone and sulbactam-related eosinophilic peritonitis: a case report and literature review.The Journal of international medical research · 2021
- Comparison of the efficacy of cefoperazone-sulbactam and other cephalosporins in the treatment of infections: A systematic review and meta-analysis.Medicine · 2025
via PubMed
Wikidata facts
- Mass
- 645.142
Show 6 more facts
- chemical formula
- C₂₅H₂₇N₉O₈S₂
- World Health Organisation international non-proprietary name
- cefoperazone
- canonical SMILES
- CCN1CCN(C(=O)C1=O)C(=O)NC(C2=CC=C(C=C2)O)C(=O)NC3C4N(C3=O)C(=C(CS4)CSC5=NN=NN5C)C(=O)O
- isomeric 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
- defined daily dose
- 4
- Commons category
- Cefoperazone
via Wikidata · CC0
~3 min read
Article
3 sectionsContents
- Spectrum of bacterial susceptibility
- Adverse effects
- References
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| tradename = | Drugs.com = | MedlinePlus = a601206 | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration =