1950. Ceftiofur

Nomenclature

CAS number: 80370-57-6
(6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[[(2-furanylcarbonyl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-3-(mercaptomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 72-(Z)-(O-methyloxime) 2-furoate (ester); Excede (Pfizer).
C19H17N5O7S3; mol wt 523.56.
C 43.59%, H 3.27%, N 13.38%, O 21.39%, S 18.37%.

Description and references

Broad spectrum, third generation cephalosporin antibiotic. Prepn: B. Labeeuw, A. Salhi, EP 36812; eidem, US 4464367 (1981, 1984 both to Sanofi). In vivo and in vitro antibacterial activity and β-lactamase stability: R. J. Yancey et al., Am. J. Vet. Res. 48, 1050 (1987). HPLC determn in swine tissue: M. G. Beconi-Barker et al., J. Chromatogr. B 673, 231 (1995); in bovine plasma: G. A. Jacobson et al., J. Pharm. Biomed. Anal. 40, 1249 (2006). Safety assessment in horses: C. R. Mahrt, Am. J. Vet. Res. 53, 2201 (1992). Review of use in food animals: R. E. Hornish, S. F. Kotarski, Curr. Top. Med. Chem. 2, 717-731 (2002).

Chemical structure

Derivative

Monosodium salt.

Nomenclature

CAS number: 104010-37-9
CM-31916; U-64279E; Naxcel (Pfizer); Spectramast (Pfizer).
C19H16N5NaO7S3; mol wt 545.54.
C 41.83%, H 2.96%, N 12.84%, Na 4.21%, O 20.53%, S 17.63%.

Derivative

Monohydrochloride.

Nomenclature

CAS number: 103980-44-5
U-67279A; Excenel (Pfizer).
C19H17N5O7S3.HCl; mol wt 560.02.
C 40.75%, H 3.24%, N 12.51%, O 20.00%, S 17.18%, Cl 6.33%.

Therapeutic Category (Veterinary)

Antibacterial.