CHEBI:3493 - cefoperazone

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ChEBI Name cefoperazone
ChEBI ID CHEBI:3493
Definition A semi-synthetic parenteral cephalosporin with a tetrazolyl moiety that confers beta-lactamase resistance.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:258120
Supplier Information ChemicalBook:CB4752040, eMolecules:3715751, Selleckchem:cefoperazone-cefobid, ZINC000003830432
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Wikipedia License
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. It was patented in 1974 and approved for medical use in 1981. Cefoperazone/sulbactam (Sulperazon) is a co-formulation with sulbactam.
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Formula C25H27N9O8S2
Net Charge 0
Average Mass 645.66700
Monoisotopic Mass 645.14240
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
InChIKey GCFBRXLSHGKWDP-XCGNWRKASA-N
SMILES CCN1CCN(C(=O)N[C@@H](C(=O)N[C@H]2[C@H]3SCC(CSc4nnnn4C)=C(N3C2=O)C(O)=O)c2ccc(O)cc2)C(=O)C1=O
Roles Classification
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
drug allergen
Any drug which causes the onset of an allergic reaction.
(via cephalosporin )
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
drug allergen
Any drug which causes the onset of an allergic reaction.
(via cephalosporin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cefoperazone (CHEBI:3493) has role antibacterial drug (CHEBI:36047)
cefoperazone (CHEBI:3493) is a cephalosporin (CHEBI:23066)
IUPAC Names
(6R,7R)-7-{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
7β-{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetyl]amino}-3-[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl-3,4-didehydrocepham-4-carboxylic acid
INNs Sources
cefoperazone ChemIDplus
cefoperazono ChemIDplus
cefoperazonum ChemIDplus
Synonyms Sources
(6R,7R)-7-((R)-2-(4-Ethyl-2,3-dioxo-1-piperazinylcarboxamido)-2-(4-hydroxyphenyl)acetamido)-3-((1-methyl-1H-tetrazol-5-yl)thiomethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure ChemIDplus
(6R,7R)-7-[[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 DrugBank
cefobid ChEBI
cefoperazon ChEBI
Cefoperazone KEGG COMPOUND
CPZ KEGG DRUG
Manual Xrefs Databases
1836 VSDB
543 DrugCentral
C06883 KEGG COMPOUND
Cefoperazone Wikipedia
D07645 KEGG DRUG
DB01329 DrugBank
LSM-15520 LINCS
View more database links
Registry Numbers Types Sources
6050252 Reaxys Registry Number Reaxys
62893-19-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
18 July 2017