9151. Tepoxalin

Nomenclature

CAS number: 103475-41-8
5-(4-Chlorophenyl)-N-hydroxy-1-(4-methoxyphenyl)-N-methyl-1H-pyrazole-3-propanamide; 3-[5-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-pyrazolyl]-N-hydroxy-N-methylpropanamide; ORF-20485; RWJ-20485; Zubrin (Schering-Plough).
C20H20ClN3O3; mol wt 385.84.
C 62.26%, H 5.22%, Cl 9.19%, N 10.89%, O 12.44%.

Description and references

Dual inhibitor of cyclooxygenase and 5-lipoxygenase. Prepn: M. P. Wachter, M. P. Ferro, EP 248594; eidem, US 4826868 (1987, 1989, both to Ortho); W. V. Murray, S. K. Hadden, J. Org. Chem. 57, 6662 (1992). LC/MS characterization of impurities and degradation products: D. J. Burinsky et al., J. Pharm. Sci. 85, 159 (1996). Mechanism of action: S. S. C. Tam et al., J. Biol. Chem. 270, 13948 (1995). Toxicity study in rats, dogs: E. V. Knight et al., Fundam. Appl. Toxicol. 33, 38 (1996). Pharmacological profile in animal models: D. C. Argentieri et al., J. Pharmacol. Exp. Ther. 271, 1399 (1994); in man: M. Depré et al., Int. J. Clin. Pharmacol. Res. 16, 1 (1996). Bioavailability in dogs: L. M. Homer et al., J. Vet. Pharmacol. Ther. 28, 287 (2005).

Chemical structure

Properties

Crystals from ethyl acetate + hexane, mp 124-126°.

Therapeutic Category (Veterinary)

Anti-inflammatory.