587. Ampiroxicam

Nomenclature

CAS number: 99464-64-9
Carbonic acid ethyl 1-[[2-methyl-1,1-dioxido-3-[(2-pyridinylamino)carbonyl]-2H-1,2-benzothiazin-4-yl]oxy]ethyl ester; carbonic acid ethyl 1-[[2-methyl-3-[(2-pyridinylamino)carbonyl]-2H-1,2-benzothiazin-4-yl]oxy]ethyl ester S,S-dioxide; (±)-4-(1-hydroxyethoxy)-2-methyl-N-2-pyridyl-2H-1,2-benzothiazine-3-carboxamide ethyl carbonate (ester) 1,1-dioxide; 4-[1-(ethoxycarbonyloxy)ethoxy]-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide; CP-65703; Flucam (Pfizer).
C20H21N3O7S; mol wt 447.46.
C 53.68%, H 4.73%, N 9.39%, O 25.03%, S 7.17%.

Description and references

Prodrug of piroxicam, q.v. Prepn: A. Marfat, EP 147177; idem, US 4551452 (both 1985 to Pfizer). Clinical pharmacokinetics: F. C. Falkner et al., Xenobiotica 20, 645 (1990). Toxicity study: M. Iijima et al., Oyo Yakuri 43, 1 (1992); C.A. 116, 187689k (1992). Pharmacology: T. J. Carty et al., Agents Actions 39, 157 (1993). Clinical trial in oral postoperative pain: K. Kurita et al., Oral. Ther. Pharmacol. 10, 138 (1991); in rheumatoid arthritis: S. Irimajiri et al., Jpn. J. Inflammation 12, 81 (1992).

Chemical structure

Properties

White crystals from toluene, mp 159-161°. LD50 orally in male, female rats: 1798, 747 mg/kg (Iijima).

Therapeutic Category

Anti-inflammatory.

Keywords

Anti-inflammatory (Nonsteroidal); Thiazinecarboxamides