Cefoperazone

Cefoperazone

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601206
ATC code	J01DD12 (WHO) Template:ATCvet
Pharmacokinetic data
Excretion	Hepatic
Identifiers
IUPAC name (6R,7R)-7-[(2R)-2-{[(4-Ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetamido]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number	62893-19-0 Y
PubChem CID	44185
DrugBank	DB01329 Y
ChemSpider	40206 Y
UNII	7U75I1278D
KEGG	D07645 Y
ChEMBL	ChEMBL507674 Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C25H27N9O8S2
Molar mass	645.67 g/mol
3D model (JSmol)	Interactive image
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@@H](c3ccc(O)cc3)NC(=O)N4C(=O)C(=O)N(CC)CC4)CSc5nnnn5C)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 Y Key:GCFBRXLSHGKWDP-XCGNWRKASA-N Y
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Cefoperazone is a third-generation cephalosporin antibiotic, marketed by Pfizer under the name Cefobid, and also marked by Pharco B International under the name Cefazone and also marketed by Sigmatec Pharmaceuticals under the name Cefoperazone. It is one of few cephalosporin antibiotics effective in treating Pseudomonas bacterial infections which are otherwise resistant to these antibiotics. Cefina-SB is a combination of sulbactam and cefoperazone. Cefoperazone exerts its bactericidal effect by inhibiting the bacterial cell wall synthesis, and sulbactam acts as a beta-lactamase inhibitor, to increase the antibacterial activity of cefoperazone against beta-lactamase-producing organisms. In some countries, the combination is sold as Sulperazone. Gepach International markets this combination of cefoperazone with sulbactam under the brand name Bacperazone.In India and SriLanka (Cefoperazone-Sulbactam) is manufacterd by Pfizer under the brand name of Magnex/Magnex-Forte depending on the Cefoperazone-Sulbactam ratio.

Spectrum of bacterial susceptibility

Cefoperazone has a broad spectrum of activity and has been used to target bacteria responsible for causing infections of the respiratory and urinary tract, skin, and the female genital tract. The following represents MIC susceptibility data for a few medically significant microorganisms.

• Haemophilus influenzae: 0.12 - 0.25 µg/ml
• Staphylococcus aureus: 0.125 - 32 µg/ml
• Streptococcus pneumoniae: ≤0.007 - 1 µg/ml

Adverse effects

Cefoperazone contains an N-methylthiotetrazole (NMTT or 1-MTT) side chain. As the antibiotic is broken down in the body, it releases free NMTT, which can cause hypoprothrombinemia (likely due to inhibition of the enzyme vitamin K epoxide reductase) and a reaction with ethanol similar to that produced by disulfiram (Antabuse), due to inhibition of aldehyde dehydrogenase.