9148. Tenoxicam

Nomenclature

CAS number: 59804-37-4
4-Hydroxy-2-methyl-N-2-pyridinyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide; Ro-12-0068; Alganex (Roche); Dolmen (Sigma-Tau); Liman (Kali-Chemie); Mobiflex (Roche); Rexalgan (Dompé); Tilatil (Roche); Tilcotil (Roche).
C13H11N3O4S2; mol wt 337.37.
C 46.28%, H 3.29%, N 12.46%, O 18.97%, S 19.01%.

Description and references

Nonsteroidal anti-inflammatory agent. Prepn: O. Hromatka et al., DE 2537070 (1976 to Hoffmann-La Roche), C.A. 85, 63077 (1976). Pharmacology: Y. Tanaka et al., Nippon Yakurigaku Zasshi 77, 531 (1981), C.A. 95, 35473 (1981). HPLC determn in plasma: M. E. Pickup et al., J. Chromatogr. 225, 493 (1981). Comparative study vs aspirin in normal volunteers: H. A. Bird et al., Curr. Med. Res. Opin. 8, 9 (1982). Preliminary review of pharmacology, therapeutic efficacy and mechanism of action: J. P. Gonzalez, P. A. Todd, Drugs 34, 289-310 (1987). Comprehensive description: A. M. Al-Obaid, M. S. Mian, Anal. Profiles Drug Subs. Excip. 22, 431-459 (1993).

Chemical structure

Properties

Crystals from xylene, mp 209-213° (dec). Soly (mg/ml): water 0.045; ethanol <1; methanol <1; acetone 2; dichloromethane 10; chloroform 8; DMSO 63. uv max (ethanol): 205, 265, 360 nm (ε 16422.12, 10127.42, 12544.21). pKa1 5.3, pKa2 1.1. Partition coefficient (octanol/water): 0.3 (pH 7.4); 3.5 (pH 1.2).

Therapeutic Category

Anti-inflammatory.

Keywords

Anti-inflammatory (Nonsteroidal); Thiazinecarboxamides