1930. Cefoperazone

Nomenclature

CAS number: 62893-19-0
(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; 7-[d-(-)-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-α-(4-hydroxyphenyl)acetamido]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-3-cephem-4-carboxylic acid.
C25H27N9O8S2; mol wt 645.67.
C 46.50%, H 4.21%, N 19.52%, O 19.82%, S 9.93%.

Description and 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.

Chemical structure

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.

Derivative

Sodium salt.

Nomenclature

CAS number: 62893-20-3
CP-52640-2; T-1551; 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).
C25H26N9NaO8S2; mol wt 667.65.
C 44.97%, H 3.93%, N 18.88%, Na 3.44%, O 19.17%, S 9.61%.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephalosporins