4103. Floctafenine

Nomenclature

CAS number: 23779-99-9
2-[[8-(Trifluoromethyl)-4-quinolinyl]amino]benzoic acid 2,3-dihydroxypropyl ester; N-[8-(trifluoromethyl)-4-quinolyl]anthranilic acid 2,3-dihydroxypropyl ester; 4-[o-(2′,3′-dihydroxypropyloxycarbonyl)phenyl]amino-8-trifluoromethylquinoline; 8-trifluoromethyl-7-deschloroglafenine; R-4318; RU-15750; Idalon (HMR); Idarac (HMR); Novodolan (HMR).
C20H17F3N2O4; mol wt 406.36.
C 59.11%, H 4.22%, F 14.03%, N 6.89%, O 15.75%.

Description and references

Prepn: A. Allais, J. Meier, DE 1815467; eidem, US 3644368 (1969, 1972, both to Roussel-UCLAF); G. Mouzin et al., Synthesis 1980, 54. Analgesic activity: Allais et al., Chim. Ther. 8, 154 (1973); M. Peterfalvi et al., Arch. Int. Pharmacodyn. Ther. 216, 97 (1975). Clinical investigation: Stenport, Curr. Ther. Res. 18, 303 (1975). Toxicology: R. Glomot et al., Toxicol. Appl. Pharmacol. 36, 173 (1976). Metabolism: R. K. Lynn et al., J. Clin. Pharmacol. 19, 20 (1979).

Chemical structure

Properties

Crystals from methanol, mp 179-180°. Sol in alcohol, acetone; very slightly sol in ether, chloroform, methylene chloride. Insol in water. LD50 in male mice, rats (mg/kg): 3400, 960 orally; 180, 160 i.v. (Glomot).

Therapeutic Category

Analgesic.

Keywords

Analgesic; Non-opioids; Anthranilic Acid Derivatives