Title: Valdecoxib
CAS Registry Number: 181695-72-7
CAS Name: 4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide
Manufacturers' Codes: SC-65872
Trademarks: Bextra (Pharmacia & Upjohn)
Molecular Formula: C16H14N2O3S
Molecular Weight: 314.36
Percent Composition: C 61.13%, H 4.49%, N 8.91%, O 15.27%, S 10.20%
Literature References: Selective cyclooxygenase-2 (COX-2) inhibitor. Active metabolite of parecoxib,
q.v. Prepn: J. J. Talley
et al., WO 9625405 (1996 to Searle);
eidem, US 5633272 (1997); and activity:
eidem,
J. Med. Chem. 43, 775 (2000). Chromatographic determn of purity: D. A. Roston
et al., J. Pharm. Biomed. Anal. 26, 339 (2001). Gastrointestinal tolerability study: G. M. Eisen
et al., Aliment. Pharmacol. Ther. 21, 591 (2005). Clinical trial in hip arthroplasty: F. Camu
et al., Am. J. Ther. 9, 43 (2002). Clinical comparison with oxycodone/acetominophen in dental pain: S. E. Daniels
et al., J. Am. Dent. Assoc. 133, 611 (2002). Clinical trial in migraine: D. Kudrow
et al., Headache 45, 1151 (2005). Review of clinical experience: M. Goldman, S. Schutzer,
Formulary 37, 68-77 (2002); of clinical efficacy and safety: G. P. Joshi,
Expert Rev. Neurother. 5, 11-24 (2005).
Properties: Crystals, mp 155-157°. Soly at 25°(mg/ml): water 10 (pH 7.0). Sol in methanol, ethanol; freely sol in organic solvents and alkaline (pH = 12) aqueous solns.
Melting point: mp 155-157°
Therap-Cat: Anti-inflammatory; analgesic.
Keywords: Anti-inflammatory (Nonsteroidal); Cyclooxygenase-2 Selective Inhibitor; Analgesic (Non-Narcotic).
