6343. Nabumetone

Nomenclature

CAS number: 42924-53-8
4-(6-Methoxy-2-naphthalenyl)-2-butanone; 4-(6-methoxy-2-naphthyl)-butan-2-one; BRL-14777; Arthaxan (GSK); Balmox (GSK); Consolan (Novo); Nabuser (Geymonat); Relafen (GSK); Relifen (GSK); Relifex (GSK).
C15H16O2; mol wt 228.29.
C 78.92%, H 7.06%, O 14.02%.

Description and references

Nonacidic, lipophillic prodrug; metabolized in vivo to 6-methoxy-2-naphthylacetic acid which inhibits prostaglandin synthesis. Prepn: A. W. Lake, C. J. Rose, DE 2442305; eidem, US 4061779 (1975, 1977 both to Beecham); A. C. Goudie et al., J. Med. Chem. 21, 1260 (1978). Pharmacology: E. A. Boyle et al., J. Pharm. Pharmacol. 34, 562 (1982); B. Nunn, P. D. Chamberlain, ibid. 576. Metabolism: R. E. Haddock et al., Xenobiotica 14, 327 (1984). HPLC determn in plasma: J. E. Ray, R. O. Day, J. Chromatogr. 336, 234 (1984). Symposia on pharmacology, pharmacokinetics and clinical efficacy: Int. Congr. Symp. Ser. - R. Soc. Med. 69, 1-215 (1985); J. Rheumatol. 19, Suppl. 36, 1-91 (1992). Review: S. L. Dahl, Ann. Pharmacother. 27, 456-463 (1993).

Chemical structure

Properties

Crystals from ethanol, mp 80°.

Therapeutic Category

Anti-inflammatory; analgesic.

Keywords

Anti-inflammatory (Nonsteroidal)