4147. Flunixin

Nomenclature

CAS number: 38677-85-9
2-[[2-Methyl-3-(trifluoromethyl)phenyl]amino]-3-pyridinecarboxylic acid; 2-(2-methyl-3-trifluoromethylanilino)nicotinic acid; 2-(α3,α3,α3-trifluoro-2,3-xylidino)nicotinic acid; Sch-14714.
C14H11F3N2O2; mol wt 296.24.
C 56.76%, H 3.74%, F 19.24%, N 9.46%, O 10.80%.

Description and references

Cyclooxygenase inhibitor. Prepn: M. H. Sherlock, N. Sperber, BE 679271; eidem, US 3337570 (1966, 1967 both to Schering). Prepn of the acid and meglumine salt: M. H. Sherlock, BE 812772; idem, US 3839344 (both 1974 to Schering). Pharmacodynamics in horses: M. M. Hardee, J. N. Moore, Res. Vet. Sci. 40, 152 (1986); and pharmacokinetics: L. R. Soma et al., J. Vet. Pharmacol. Ther. 15, 292 (1992). GC determn in urine: M. Johansson, E. -L. Anlér, J. Chromatogr. 427, 55 (1988). Clinical evaluation in horses: J. W. Houdeshell, P. W. Hennessey, J. Equine Med. Surg. 1, 57 (1977). Experimental use in food-producing animals: M. Kopcha, A. S. Ahl, J. Am. Vet. Med. Assoc. 194, 45 (1989). Comparative toxicological study in horses: C. G. MacAllister et al., ibid. 202, 71 (1993).

Chemical structure

Properties

Crystals from acetone/hexane, mp 226-228°. pKa′ 5.82.

Derivative

Meglumine salt.

Nomenclature

CAS number: 42461-84-7
Banamine (Schering-Plough); Binixin (Bayer); Finadyne (Fisons).
C14H11F3N2O2.C7H17NO5; mol wt 491.46.
C 51.32%, H 5.74%, F 11.60%, N 8.55%, O 22.79%.

Properties

Colorless cryst from ethanol/ether, mp 135-137°. Crystals from acetonitrile, mp 136-139°. Sol in water.

Therapeutic Category (Veterinary)

Anti-inflammatory; analgesic; antipyretic.