Cefoperazone

Cefoperazone

Systematic (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
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601206
Pregnancy cat.	?
Legal status	?
Pharmacokinetic data
Excretion	Hepatic
Identifiers
CAS number	62893-19-0
ATC code	J01DD12 QJ51DD12
PubChem	CID 44185
DrugBank	DB01329
ChemSpider	40206 Y
UNII	7U75I1278D Y
KEGG	D07645 Y
ChEMBL	CHEMBL507674 Y
Chemical data
Formula	C25H27N9O8S2
Mol. mass	645.67 g/mol
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
Y (what is this?)  (verify)

Cefoperazone is a third generation cephalosporin antibiotic, marketed by Pfizer under the name Cefobid, and also marked by pharco B international under the name of Cefazone and also marketed by "sigmatec" 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

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.