Cefoperazone

Cefoperazone
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601206
ATC code	J01DD12 (WHO) QJ51DD12 (WHO);
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 ;
PubChem CID	44185;
DrugBank	DB01329 ;
ChemSpider	40206 ;
UNII	7U75I1278D;
KEGG	D07645 ;
ChEMBL	ChEMBL507674 ;
CompTox Dashboard (EPA)	DTXSID2022759 ;
ECHA InfoCard	100.057.936
Chemical and physical data
Formula	C25H27N9O8S2
Molar mass	645.67 g·mol−1
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 ; Key:GCFBRXLSHGKWDP-XCGNWRKASA-N ;
	(verify)

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.[1] Cefoperazone/sulbactam (Sulperazon) is a co-formulation with sulbactam.

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[2]

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 effect), due to inhibition of aldehyde dehydrogenase.[3]

Mechanism of action

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.

References

Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 494. ISBN 9783527607495.
"Cefoperazone (Cefobid) - The Antimicrobial Index Knowledgebase - TOKU-E". antibiotics.toku-e.com.
Stork CM (2006). "Antibiotics, antifungals, and antivirals". In Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.). Goldfrank's toxicologic emergencies. New York: McGraw-Hill. p. 847. ISBN 0-07-143763-0. Retrieved 2009-07-03.

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[Fis2006-1] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 494. ISBN 9783527607495.

[2] "Cefoperazone (Cefobid) - The Antimicrobial Index Knowledgebase - TOKU-E". antibiotics.toku-e.com.

[Goldfrank-3] Stork CM (2006). "Antibiotics, antifungals, and antivirals". In Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.). Goldfrank's toxicologic emergencies. New York: McGraw-Hill. p. 847. ISBN 0-07-143763-0. Retrieved 2009-07-03.