3887. Etoricoxib

Nomenclature

CAS number: 202409-33-4
5-Chloro-6′-methyl-3-[4-(methylsulfonyl)phenyl]-2,3′-bipyridine; 5-chloro-3-(4-methylsulfonyl)phenyl-2-(2-methyl-5-pyridinyl)pyridine; MK-663; MK-0663; Arcoxia (Merck & Co.).
C18H15ClN2O2S; mol wt 358.84.
C 60.25%, H 4.21%, Cl 9.88%, N 7.81%, O 8.92%, S 8.94%.

Description and references

Selective cyclooxygenase-2 (COX-2) inhibitor. Prepn: D. Dube et al., WO 9803484; eidem, US 5861419 (1998, 1999 both to Merck Frosst); R. W. Friesen et al., Bioorg. Med. Chem. Lett. 8, 2777 (1998). Practical synthesis: I. W. Davies et al., J. Org. Chem. 65, 8415 (2000). HPLC determn in urine and plasma: C. Z. Matthews et al., J. Chromatogr. B 751, 237 (2001). Pharmacology: D. Riendeau et al., J. Pharmacol. Exp. Ther. 296, 558 (2001); A. Dallob et al., J. Clin. Pharmacol. 43, 573 (2003). Clinical comparison with indomethacin in acute gouty arthritis: H. R. Schumacher, Jr. et al., Br. Med. J. 324, 1488 (2002). Clinical trial in rheumatoid arthritis: A. K. Matsumoto et al., J. Rheumatol. 29, 1623 (2002); in osteoarthritis: S. P. Curtis et al., BMC Musculoskelet. Disord. 6, 58 (2005); in ankylosing spondylitis: D. van der Heijde et al., Arthritis Rheum. 52, 1205 (2005). Gastrointestinal safety profile in inflammatory bowel diseases: Y. El Miedany et al., Am. J. Gastroenterol. 101, 311 (2006). Review of pharmacology and clinical development: P. Patrignani et al., Expert Opin. Pharmacother. 4, 265-284 (2003).

Chemical structure

Properties

White solid, mp 127-128°. pKa 4.5. uv max (acetonitrile-phosphate buffer): 238, 280 nm.

Therapeutic Category

Anti-inflammatory.

Keywords

Anti-inflammatory (Nonsteroidal); Cyclooxygenase-2 Selective Inhibitor