Title: Ribavirin
CAS Registry Number: 36791-04-5
CAS Name: 1-b-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide
Additional Names: RTCA; tribavirin
Manufacturers' Codes: ICN-1229
Trademarks: Copegus (Roche); Rebetol (Schering-Plough); Viramid (Alfa); Virazide (Valeant); Virazole (Valeant)
Molecular Formula: C8H12N4O5
Molecular Weight: 244.20
Percent Composition: C 39.35%, H 4.95%, N 22.94%, O 32.76%
Literature References: Purine nucleoside analog; inhibits inosine monophosphate dehydrogenase (IMPDH). Prepn: J. T. Witkowski, R. Robins, DE 2220246; eidem, US 3798209 (1972, 1974 both to ICN); J. T. Witkowski et al., J. Med. Chem. 15, 1150 (1972); eidem, J. Carbohydr. Nucleosides Nucleotides 5, 363 (1978). Regioselective synthesis: Y. Ito et al., Tetrahedron Lett. 1979, 2521. NMR study: G. P. Kreishman et al., J. Am. Chem. Soc. 94, 5894 (1972). Crystal structure: P. Prusiner, M. Sundaralingam, Nature New Biol. 244, 116 (1973). Teratogenicity study: D. M. Kochhar et al., Toxicol. Appl. Pharmacol. 52, 99 (1980). Review of antiviral activity: R. W. Sidwell et al., Pharmacol. Ther. 6, 123-146 (1979); of clinical experience: H. Fernandez et al., Eur. J. Epidemiol. 2, 1-14 (1986); of molecular modes of action: J. L. Patterson, R. Fernandez-Larsson, Rev. Infect. Dis. 12, 1139-1146 (1990). Clinical trial in infants with respiratory syncytial viral infection: C. B. Hall et al., N. Engl. J. Med. 308, 1443 (1983); in combination with interferon alfa-2b in hepatitis C: O. Reichard et al., Lancet 351, 83 (1998).
Properties: White to off-white powder. Freely sol in water; slightly sol in anhydrous alcohol. Exists in two polymorphic forms: mp 166-168° (aq ethanol); mp 174-176° (ethanol) (Witkowski, 1972). Also reported as mp 180-182° (Ito). [a]D25 -36.5° (c = 1 in water); [a]D20 -38° (c = 1 in water). LD50 i.p. in mice: 1.3 g/kg; orally in rats: 5.3 g/kg (Witkowski, 1972).
Melting point: mp 166-168° (aq ethanol); mp 174-176° (ethanol) (Witkowski, 1972); mp 180-182° (Ito)
Optical Rotation: [a]D25 -36.5° (c = 1 in water); [a]D20 -38° (c = 1 in water)
Toxicity data: LD50 i.p. in mice: 1.3 g/kg; orally in rats: 5.3 g/kg (Witkowski, 1972)
Therap-Cat: Antiviral.
Keywords: Antiviral; IMPDH Inhibitor. |