Cefoperazone

Title: Cefoperazone
CAS Registry Number: 62893-19-0
CAS Name: (6R,7R)-7-[[(2R)-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino](4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Additional Names: 7-[D-(-)-a-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-a-(4-hydroxyphenyl)acetamido]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-3-cephem-4-carboxylic acid
Molecular Formula: C25H27N9O8S2
Molecular Weight: 645.67
Percent Composition: C 46.50%, H 4.21%, N 19.52%, O 19.82%, S 9.93%
Literature References: Broad spectrum third generation cephalosporin antibiotic. Prepn: I. Saikawa et al., BE 837682; eidem, US 4410522 (1976, 1983 both to Toyama); eidem, Yakugaku Zasshi 99, 929 (1979). Stability in aq soln: eidem, ibid. 1207. In vitro activity: M. V. Borobio et al., Antimicrob. Agents Chemother. 17, 129 (1980). Kinetics in rats: J. Fabre et al., Schweiz. Med. Wochenschr. 110, 264 (1980); in humans: A. F. Allaz, ibid. 109, 1999 (1979). Review of pharmacology and therapeutic efficacy: R. N. Brogden et al., Drugs 22, 423-460 (1981). Symposium on clinical studies: ibid. Suppl. 1, 1-124.
Properties: Crystals from acetonitrile/water, mp 169-171° (hydrated). Stable at pH 4.0-7.0; slightly unstable in acid; highly unstable in alkaline soln.
Melting point: mp 169-171° (hydrated)
Derivative Type: Sodium salt
CAS Registry Number: 62893-20-3
Manufacturers' Codes: CP-52640-2; T-1551
Trademarks: Bioperazone (Biopharma); Cefazone (Firma); Cefobid (Pfizer); Cefobine (Pfizer); Cefobis (Pfizer); Cefogram (Metapharma); Cefoneg (Tosi); Cefosint (Proter); Dardum (Lisapharma); Farecef (Lafare); Kefazon (Esseti); Novobiocyl (Francia); Pathozone (Pfizer); Peracef (Pfizer); Perocef (Pulitzer); Tomabef (Aandersen)
Molecular Formula: C25H26N9NaO8S2
Molecular Weight: 667.65
Percent Composition: C 44.97%, H 3.93%, N 18.88%, Na 3.44%, O 19.17%, S 9.61%
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.
Ceforanide Cefoselis Cefotetan Cefotiam Cefoxitin

Cefoperazone
Cefoperazone.svg
Cefoperazone ball-and-stick.png
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
Legal status  ?
Pharmacokinetic data
Excretion Hepatic
Identifiers
CAS number 62893-19-0 YesY
ATC code J01DD12 QJ51DD12
PubChem CID 44185
DrugBank DB01329
ChemSpider 40206 YesY
UNII 7U75I1278D YesY
KEGG D07645 YesY
ChEMBL CHEMBL507674 YesY
Chemical data
Formula C25H27N9O8S2 
Mol. mass 645.67 g/mol
 YesY (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