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36791-04-5 , Ribavirin, CAS:36791-04-5

36791-04-5, Ribavirin,
CAS:36791-04-5
C8H12N4O5 / 244.20
MFCD00058564

Ribavirin, 利巴韦林

Ribavirin is an antiviral agent used for the treatment of hepatitis C, respiratory syncytial virus infection and influenza. It is a monocarboxylic acid derived from vitamin B2. Ribavirin inhibits viral replication by interfering with the function of RNA polymerase. Ribavirin also has immunosuppressive properties that can be useful in treating autoimmune disorders such as systemic lupus erythematosus and it has been approved by the FDA for treatment of chronic hepatitis C virus (HCV) genotype 1 infection with compensated liver disease or decompensated liver disease with or without HCV genotype 3 infection. The antiviral activity of ribavirin against other viruses, including HIV-1, herpes simplex virus type 2, varicella zoster virus, cytomegalovirus, respiratory syncytial virus, influenza A and B viruses has been reported but not largely studied.

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.

CAS Number36791-04-5
Product NameRibavirin
IUPAC Name1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide
Molecular FormulaC8H12N4O5
Molecular Weight244.20 g/mol
InChIInChI=1S/C8H12N4O5/c9-6(16)7-10-2-12(11-7)8-5(15)4(14)3(1-13)17-8/h2-5,8,13-15H,1H2,(H2,9,16)/t3-,4-,5-,8-/m1/s1
InChI KeyIWUCXVSUMQZMFG-AFCXAGJDSA-N
SMILESO=C(C1=NN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=N1)N
Solubilitygreater than or equal to 100 mg/mL at 66° F (NTP, 1992)
Soluble
0.58 M
Water-soluble
Slightly soluble in alcohol.
In water, 142 mg/mL at 25 °C
3.32e+01 g/L
SynonymsICN 1229, ICN-1229, ICN1229, Rebetol, Ribamide, Ribamidil, Ribamidyl, Ribasphere, Ribavirin, Ribovirin, Tribavirin, Vilona, Viramide, Virazide, Virazole
Canonical SMILESC1=NC(=NN1C2C(C(C(O2)CO)O)O)C(=O)N
Isomeric SMILESC1=NC(=NN1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)N
CAS No: 36791-04-5 Synonyms: 1-b-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamideViramidVirazole MDL No: MFCD00058564 Chemical Formula: C8H12N4O5 Molecular Weight: 244.20
References: 1. Crotty S, Maag D, Arnold JJ, Zhong W, Lau JYN, et al., Nature Medicine 2000, 6, 1375-1379


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