3948. Febuxostat

Nomenclature

CAS number: 144060-53-7
2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methyl-5-thiazolecarboxylic acid; 2-(3-cyano-4-isobutyloxyphenyl)-4-methyl-5-thiazolecarboxylic acid; TEI-6720; TMX-67.
C16H16N2O3S; mol wt 316.37.
C 60.74%, H 5.10%, N 8.85%, O 15.17%, S 10.14%.

Description and references

Xanthine oxidase/xanthine dehydrogenase inhibitor. Prepn: S. Kondo et al., EP 513379; eidem, US 5614520 (1992, 1997 both to Teijin). Synthesis: M. Hasegawa, Heterocycles 47, 857 (1998). Mechanism of action and crystal structure study: K. Okamoto et al., J. Biol. Chem. 278, 1848 (2003). Pharmacology: Y. Osada et al., Eur. J. Pharmacol. 241, 183 (1993). Clinical pharmacokinetics: M. D. Mayer et al., Am. J. Ther. 12, 22 (2005). Clinical evaluation in hyperuricemia and gout: M. A. Becker et al., N. Engl. J. Med. 353, 2450 (2005). Review of clinical development: B. Tomlinson, Curr. Opin. Investig. Drugs 6, 1168-1178 (2005).

Chemical structure

Properties

Crystals from ethanol, mp 238-239° (dec). Also reported as crystals from acetone, mp 201-202° (Hasegawa).

Therapeutic Category

Treatment of hyperuricemia and chronic gout.

Keywords

Antigout; Xanthine Oxidase Inhibitor