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Also known as: 36791-04-5, Tribavirin, Rebetol, Virazole, Copegus, Ribasphere
Molecular Formula
C8H12N4O5
Molecular Weight
244.20  g/mol
InChI Key
IWUCXVSUMQZMFG-AFCXAGJDSA-N
FDA UNII
49717AWG6K

Ribavirin
A nucleoside antimetabolite antiviral agent that blocks nucleic acid synthesis and is used against both RNA and DNA viruses.
Ribavirin is a Nucleoside Analog Antiviral.
1 2D Structure

Ribavirin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide
2.1.2 InChI
InChI=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
2.1.3 InChI Key
IWUCXVSUMQZMFG-AFCXAGJDSA-N
2.1.4 Canonical SMILES
C1=NC(=NN1C2C(C(C(O2)CO)O)O)C(=O)N
2.1.5 Isomeric SMILES
C1=NC(=NN1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)N
2.2 Other Identifiers
2.2.1 UNII
49717AWG6K
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Icn 1229

2. Icn-1229

3. Icn1229

4. Rebetol

5. Ribamide

6. Ribamidil

7. Ribamidyl

8. Ribasphere

9. Ribovirin

10. Tribavirin

11. Vilona

12. Viramide

13. Virazide

14. Virazole

2.3.2 Depositor-Supplied Synonyms

1. 36791-04-5

2. Tribavirin

3. Rebetol

4. Virazole

5. Copegus

6. Ribasphere

7. Vilona

8. Ribavirine

9. Viramid

10. Rtca

11. Cotronak

12. Ribamide

13. Ribamidil

14. Ribavirina

15. Ribavirinum

16. Ribavirine [inn-french]

17. Ribavirinum [inn-latin]

18. Icn-1229

19. Ribavirina [inn-spanish]

20. 1-beta-d-ribofuranosyl-1,2,4-triazole-3-carboxamide

21. Ribavirin Mylan

22. Ribavirin Teva

23. 1-beta-d-ribofuranosyl-1h-1,2,4-triazole-3-carboxamide

24. Ribavirin Biopartners

25. Sch 18908

26. 1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1h-1,2,4-triazole-3-carboxamide

27. Rbv

28. Ribamidyl

29. Ribavirin (copegus)

30. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide

31. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1h-1,2,4-triazole-3-carboxamide

32. Rebetron

33. Varazid

34. Nsc-163039

35. Ribavirin Capsules

36. 1h-1,2,4-triazole-3-carboxamide, 1-beta-d-ribofuranosyl-

37. Chebi:63580

38. 49717awg6k

39. Sch-18908

40. 1-(beta-d-ribofuranosyl)-1h-1,2,4-triazole-3-carboxamide

41. Rebretron

42. Virazid

43. Virazide

44. 1h-1,2,4-triazole-3-carboxamide, 1-.beta.-d-ribofuranosyl-

45. Ribav

46. Mfcd00058564

47. Dsstox_cid_3557

48. Dsstox_rid_77081

49. Dsstox_gsid_23557

50. Rtc

51. Ravanex

52. Ribacine

53. C-virin

54. Drg-0028

55. Ribasphere (tn)

56. Virazole (tn)

57. Smr000058315

58. Copegus (tn)

59. Rebetol (tn)

60. Hsdb 6513

61. Sr-01000076112

62. Brn 0892462

63. Ribavirin Teva Pharma B.v.

64. Unii-49717awg6k

65. Ribavirine;

66. Nsc163039

67. Ribavirin [usan:usp:inn:ban]

68. Ribavirin,(s)

69. Ncgc00015904-02

70. Ribavirin, Antiviral

71. Cas-36791-04-5

72. Rg-964

73. Ro-20-9963

74. Spectrum_001826

75. 4pb1

76. Ribavirin [inn]

77. Ribavirin [jan]

78. Ribavirin [mi]

79. Ribofluranosyl Carboxamide

80. Ribavirin [hsdb]

81. Ribavirin [usan]

82. Prestwick3_000993

83. Spectrum3_001876

84. Spectrum4_001252

85. Spectrum5_002075

86. Ribavirin [vandf]

87. R-964

88. Ribavirin [mart.]

89. R 9644

90. Ribavirin [usp-rs]

91. Ribavirin [who-dd]

92. Schembl3727

93. 1-.beta.-d-ribofuranosyl-1h-1,2,4-triazole-3-carboxamide

94. Chembl1643

95. Lopac0_001063

96. Bspbio_001085

97. Bspbio_003352

98. Kbiogr_001804

99. Kbioss_002331

100. Ribavirin [ema Epar]

101. Cid_37542

102. Mls000028486

103. Mls002222317

104. Divk1c_000782

105. Spectrum1503938

106. Ribavirin (jp17/usp/inn)

107. Bpbio1_001195

108. Gtpl6842

109. Ribavirin [orange Book]

110. 1,2,4-triazole-3-carboxamide, 1-beta-d-ribofuranosyl-

111. 1-(beta-d-ribofuranosyl)-1,2,4-triazole-3-carboxamide

112. 1-.beta.-d-ribofuranosyl-1,2,4-triazolo-3-carboxamide

113. Dtxsid8023557

114. Ribavirin [ep Monograph]

115. Hms502h04

116. Kbio1_000782

117. Kbio2_002328

118. Kbio2_004896

119. Kbio2_007464

120. Kbio3_002854

121. Ribavirin [usp Monograph]

122. Ninds_000782

123. Hms2090l15

124. Hms2094o09

125. Hms2098g07

126. Hms2232p07

127. Hms3263e08

128. Hms3715g07

129. Pharmakon1600-01503938

130. 66510-90-5

131. Hy-b0434

132. Zinc1035331

133. Tox21_110259

134. Tox21_200967

135. Tox21_501063

136. Bdbm50154375

137. Ccg-38985

138. Nsc758650

139. S2504

140. Ribavirin 100 Microg/ml In Methanol

141. Akos001715163

142. Tox21_110259_1

143. Db00811

144. Gs-3572

145. Lp01063

146. Nsc-758650

147. Sdccgsbi-0051033.p004

148. Idi1_000782

149. Smp1_000261

150. Ncgc00090726-01

151. Ncgc00090726-03

152. Ncgc00090726-04

153. Ncgc00090726-05

154. Ncgc00090726-06

155. Ncgc00090726-07

156. Ncgc00090726-08

157. Ncgc00090726-09

158. Ncgc00090726-12

159. Ncgc00090726-25

160. Ncgc00090726-30

161. Ncgc00258520-01

162. Ncgc00261748-01

163. 252269-50-4

164. As-34178

165. Bcp0726000138

166. Ribavirin Component Of Peginterferon

167. Sbi-0051033.p003

168. Ab00430481

169. Eu-0101063

170. R0077

171. En300-59237

172. D00423

173. Ab00430481-15

174. Ab00430481-16

175. Ab00430481_17

176. Ab00430481_18

177. 1-beta-ribofuranosyl-1,2,4-triazole-3-carboamide

178. 791r045

179. A823370

180. Q421862

181. Ribavirin 100 Microg/ml In Acetonitrile:methanol

182. Sr-01000721904

183. 1-b-d-ribofuranosyl-1,2,4-triazole-3-carboxamide

184. 1-ss-d-ribofuranosyl-1,2,4-triazole-3-carboxamide

185. Sr-01000076112-2

186. Sr-01000076112-3

187. Sr-01000076112-4

188. Sr-01000721904-2

189. Brd-k60369935-001-02-7

190. Brd-k60369935-001-18-3

191. Sr-01000076112-11

192. 1-?-d-ribofuranosyl-1h-1,2,4-triazole-3-carboxamide

193. Ribavirin, British Pharmacopoeia (bp) Reference Standard

194. Z1522567185

195. 1-(beta -d-ribofuranosyl)-1,2,4-triazole-3-carboxamide

196. Ribavirin, European Pharmacopoeia (ep) Reference Standard

197. Ribavirin, United States Pharmacopeia (usp) Reference Standard

198. Ribavirin, Pharmaceutical Secondary Standard; Certified Reference Material

199. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,2,4-triazole-3-carboxamide

200. 1-[(2r,3s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,2,4-triazole-3-carboxamide

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 244.20 g/mol
Molecular Formula C8H12N4O5
XLogP3-1.8
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count3
Exact Mass244.08076950 g/mol
Monoisotopic Mass244.08076950 g/mol
Topological Polar Surface Area144 Ų
Heavy Atom Count17
Formal Charge0
Complexity304
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 10  
Drug NameCopegus
PubMed HealthRibavirin
Drug ClassesAntiviral
Drug LabelCOPEGUS, ribavirin, is a nucleoside analogue with antiviral activity. The chemical name of ribavirin is 1--D-ribofuranosyl-1H-1,2,4-triazole-3-carboxamide and has the following structural formula:The empirical formula of ribavirin is C8H12N4O5 and...
Active IngredientRibavirin
Dosage FormTablet
RouteOral
Strength200mg
Market StatusPrescription
CompanyRoche

2 of 10  
Drug NameRebetol
PubMed HealthRibavirin
Drug ClassesAntiviral
Drug LabelREBETOL (ribavirin), is a synthetic nucleoside analogue (purine analogue). The chemical name of ribavirin is 1--D-ribofuranosyl-1H-1,2,4-triazole-3-carboxamide and has the following structural formula (see Figure 1).Figure 1: Structural FormulaRiba...
Active IngredientRibavirin
Dosage FormCapsule; Solution
RouteOral
Strength200mg; 40mg/ml; 200mg **indicated for use and comarketed with interferon alfa-2b, recombinant (intron a), as rebetron combination therapy**
Market StatusPrescription
CompanyMerck Sharp Dohme; Schering

3 of 10  
Drug NameRibasphere
PubMed HealthRibavirin
Drug ClassesAntiviral
Drug LabelRIBASPHERE (ribavirin, USP), is a nucleoside analogue with antiviral activity. The chemical name of ribavirin is 1-and has the following structural formula:The molecular formula of ribavirin is C8H12N4O5 and the molecular weight is 244.2. Ribavirin i...
Active IngredientRibavirin
Dosage FormCapsule
RouteOral
Strength200mg
Market StatusPrescription
CompanyThree Rivers Pharms

4 of 10  
Drug NameRibavirin
Drug LabelRIBASPHERE (ribavirin, USP), is a nucleoside analogue with antiviral activity. The chemical name of ribavirin is 1-and has the following structural formula:The molecular formula of ribavirin is C8H12N4O5 and the molecular weight is 244.2. Ribavirin i...
Active IngredientRibavirin
Dosage FormTablet; Capsule; Solution
Routeoral; Oral
Strength200mg; 600mg; 500mg; 400mg; 40mg/ml
Market StatusTentative Approval; Prescription
CompanyTeva; Aurobindo Pharma; Sandoz; Teva Pharms; Zydus Pharms Usa; Three Rivers Pharms

5 of 10  
Drug NameVirazole
Drug LabelVIRAZOLE is a brand name for ribavirin, a synthetic nucleoside with antiviral activity. VIRAZOLE for inhalation solution is a sterile, lyophilized powder to be reconstituted for aerosol administration. Each 100 mL glass vial contains 6 grams of rib...
Active IngredientRibavirin
Dosage FormFor solution
RouteInhalation
Strength6gm/vial
Market StatusPrescription
CompanyValeant Pharm Intl

6 of 10  
Drug NameCopegus
PubMed HealthRibavirin
Drug ClassesAntiviral
Drug LabelCOPEGUS, ribavirin, is a nucleoside analogue with antiviral activity. The chemical name of ribavirin is 1--D-ribofuranosyl-1H-1,2,4-triazole-3-carboxamide and has the following structural formula:The empirical formula of ribavirin is C8H12N4O5 and...
Active IngredientRibavirin
Dosage FormTablet
RouteOral
Strength200mg
Market StatusPrescription
CompanyRoche

7 of 10  
Drug NameRebetol
PubMed HealthRibavirin
Drug ClassesAntiviral
Drug LabelREBETOL (ribavirin), is a synthetic nucleoside analogue (purine analogue). The chemical name of ribavirin is 1--D-ribofuranosyl-1H-1,2,4-triazole-3-carboxamide and has the following structural formula (see Figure 1).Figure 1: Structural FormulaRiba...
Active IngredientRibavirin
Dosage FormCapsule; Solution
RouteOral
Strength200mg; 40mg/ml; 200mg **indicated for use and comarketed with interferon alfa-2b, recombinant (intron a), as rebetron combination therapy**
Market StatusPrescription
CompanyMerck Sharp Dohme; Schering

8 of 10  
Drug NameRibasphere
PubMed HealthRibavirin
Drug ClassesAntiviral
Drug LabelRIBASPHERE (ribavirin, USP), is a nucleoside analogue with antiviral activity. The chemical name of ribavirin is 1-and has the following structural formula:The molecular formula of ribavirin is C8H12N4O5 and the molecular weight is 244.2. Ribavirin i...
Active IngredientRibavirin
Dosage FormCapsule
RouteOral
Strength200mg
Market StatusPrescription
CompanyThree Rivers Pharms

9 of 10  
Drug NameRibavirin
Drug LabelRIBASPHERE (ribavirin, USP), is a nucleoside analogue with antiviral activity. The chemical name of ribavirin is 1-and has the following structural formula:The molecular formula of ribavirin is C8H12N4O5 and the molecular weight is 244.2. Ribavirin i...
Active IngredientRibavirin
Dosage FormTablet; Capsule; Solution
Routeoral; Oral
Strength200mg; 600mg; 500mg; 400mg; 40mg/ml
Market StatusTentative Approval; Prescription
CompanyTeva; Aurobindo Pharma; Sandoz; Teva Pharms; Zydus Pharms Usa; Three Rivers Pharms

10 of 10  
Drug NameVirazole
Drug LabelVIRAZOLE is a brand name for ribavirin, a synthetic nucleoside with antiviral activity. VIRAZOLE for inhalation solution is a sterile, lyophilized powder to be reconstituted for aerosol administration. Each 100 mL glass vial contains 6 grams of rib...
Active IngredientRibavirin
Dosage FormFor solution
RouteInhalation
Strength6gm/vial
Market StatusPrescription
CompanyValeant Pharm Intl

4.2 Therapeutic Uses

Antimetabolites; Antiviral Agents

National Library of Medicine, SIS; ChemIDplus Record for Ribavirin (36791-04-5), MESH Heading. Available from, as of March 15, 2006: https://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp


Antiviral

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1470


Oral and intravenous ribavirin are used in the treatment of Lassa fever and as post-exposure prophylaxis in contacts at hgh risk. It may be similarly effective with other viral hemorrhagic fevers, including hemorrhagic fever with renal syndrome, Crimean-Congo hemorrhagic fever, and Rift Valley fever. /NOT included in US product labeling/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2584


Ribavirin inhalation solution is used as a secondary agent in the treatment of influenza A an