5826. Meloxicam

Nomenclature

CAS number: 71125-38-7
4-Hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide; Metacam (Boehringer, Ing.); Mobec (Boehringer, Ing.); Mobic (Boehringer, Ing.); Mobicox (Boehringer, Ing.); Movalis (Boehringer, Ing.); Movatec (Boehringer, Ing.); Parocin (Almirall).
C14H13N3O4S2; mol wt 351.40.
C 47.85%, H 3.73%, N 11.96%, O 18.21%, S 18.25%.

Description and references

Preferential cyclooxygenase (COX-2) inhibitor. Prepn: G. Trummlitz et al., DE 2756113 (1979 to Thomae); eidem, US 4233299 (1980 to Boehringer Ingelheim). Pharmacology in horses: P. Lees et al., Br. Vet. J. 147, 97 (1991). Physicochemical properties: R.-S. Tsai et al., Helv. Chim. Acta 76, 842 (1993). Veterinary trial in dogs: A. J. Henderson et al., Prakt. Tierarzt 75, 179 (1994). Series of articles on pharmacology, mechanism of action and clinical efficacy: Br. J. Rheumatol. 35, Suppl. 1, 1-77 (1996). Clinical trials of GI tolerability in arthritis: C. Hawkey et al., ibid. 37, 937 (1998); J. Dequeker et al., ibid. 946. Review of clinical experience: R. Fleischmann et al., Expert Opin. Pharmacother. 3, 1501-1512 (2002).

Chemical structure

Properties

Crystals from ethylene chloride, mp 254° (dec). pKa: 4.08 in water; 4.24 ± 0.01 in water/ethanol (1:1); 4.63 ± 0.03 in water/ethanol (1:4). Log P (octanol/water): 3.02. LD50 orally in mice: 470 mg/kg (Trummlitz, 1980).

Therapeutic Category

Anti-inflammatory.

Therapeutic Category (Veterinary)

Anti-inflammatory.

Keywords

Anti-inflammatory (Nonsteroidal); Thiazinecarboxamides