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Identification
NameRibavirin
Accession NumberDB00811  (APRD00081, EXPT02825, DB01693)
TypeSmall Molecule
GroupsApproved
DescriptionA nucleoside antimetabolite antiviral agent that blocks nucleic acid synthesis and is used against both RNA and DNA viruses. [PubChem]
Structure
Thumb
Synonyms
1-beta-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide
1-beta-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide
RBV
Ribavirin
Ribavirina
Ribavirine
Ribavirinum
Tribavirin
External Identifiers
  • ICN 1229
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CopegusTablet, film coated200 mg/1OralGenentech, Inc.2002-12-03Not applicableUs
IbavyrTablet200 mgOralPendopharm Division Of De Pharmascience Inc2015-05-01Not applicableCanada
IbavyrTablet400 mgOralPendopharm Division Of De Pharmascience Inc2014-07-14Not applicableCanada
IbavyrTablet600 mgOralPendopharm Division Of De Pharmascience Inc2014-07-14Not applicableCanada
ModeribaTablet200 mgOralAbbvie2015-02-17Not applicableCanada
ModeribaTablet400 mgOralAbbvie2015-02-19Not applicableCanada
ModeribaTablet600 mgOralAbbvie2015-02-19Not applicableCanada
RebetolCapsule200 mgOralMerck Sharp & Dohme Limited  1999-05-07Not applicableEu
RebetolCapsule200 mg/1OralMerck Sharp & Dohme Limited  1998-06-03Not applicableUs
RebetolCapsule200 mgOralMerck Sharp & Dohme Limited  1999-05-07Not applicableEu
RebetolLiquid40 mg/mLOralMerck Sharp & Dohme Limited  2003-07-29Not applicableUs
RebetolSolution40 mg/mlOralMerck Sharp & Dohme Limited  1999-05-07Not applicableEu
RebetolCapsule200 mg/1OralMerck Sharp & Dohme Limited  1998-06-03Not applicableUs
RebetolCapsule200 mgOralMerck Sharp & Dohme Limited  1999-05-07Not applicableEu
RebetolCapsule200 mgOralMerck Sharp & Dohme Limited  1999-05-07Not applicableEu
RebetolCapsule200 mg/1OralMerck Sharp & Dohme Limited  1998-06-03Not applicableUs
VirazolePowder, for solution6 g/1Respiratory (inhalation)Valeant Pharmaceuticals North America1986-01-01Not applicableUs
VirazoleAerosol; Powder, for solution6 gRespiratory (inhalation)Valeant Canada Lp Valeant Canada S.E.C.1996-12-05Not applicableCanada
Virazole Pws 6gm/vialAerosol; Powder, for solution6 gRespiratory (inhalation)Viratek Inc.1986-12-311997-08-08Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ModeribaTablet, film coated200 mg/1OralAbbvie2014-01-20Not applicableUs
ModeribaTablet, film coated600 mg/1OralAbbvie2014-01-20Not applicableUs
ModeribaKitAbbvie2014-01-20Not applicableUs
ModeribaTablet, film coated400 mg/1OralAbbvie2014-01-20Not applicableUs
ModeribaKitAbbvie2014-01-20Not applicableUs
RibasphereTablet, film coated400 mg/1OralKadmon Pharmaceuticals2005-12-05Not applicableUs
RibasphereTablet200 mg/1OralRemedy Repack2011-11-302016-10-13Us
RibasphereTablet, film coated600 mg/1OralKadmon Pharmaceuticals2005-12-05Not applicableUs
RibasphereCapsule200 mg/1OralKadmon Pharmaceuticals2004-04-07Not applicableUs
RibasphereTablet, film coated200 mg/1OralKadmon Pharmaceuticals2005-12-05Not applicableUs
RibasphereTablet400 mg/1OralRemedy Repack2011-08-182016-11-08Us
Ribasphere RibapakTablet600 mg/1OralKadmon Pharmaceuticals2010-01-01Not applicableUs
Ribasphere RibapakKitKadmon Pharmaceuticals2012-06-01Not applicableUs
Ribasphere RibapakTablet400 mg/1OralKadmon Pharmaceuticals2010-01-01Not applicableUs
Ribasphere RibapakKitKadmon Pharmaceuticals2010-01-01Not applicableUs
RibavirinPowder, for solution6 g/1Respiratory (inhalation)Zydus Pharmaceuticals Usa, Inc.2016-12-15Not applicableUs
RibavirinTablet, film coated200 mg/1OralSandoz2006-10-03Not applicableUs
RibavirinTablet, film coated600 mg/1OralCadila Pharnmaceuticals2005-12-05Not applicableUs
RibavirinTablet, film coated400 mg/1OralZydus Pharmaceuticals Usa, Inc.2005-12-05Not applicableUs
RibavirinTablet, film coated400 mg/1OralRichmond Pharmaceuticals2008-06-01Not applicableUs
RibavirinCapsule200 mg/1OralTeva2004-10-042015-11-30Us
RibavirinCapsule200 mg/1OralAurobindo Pharma2009-09-17Not applicableUs
RibavirinCapsule200 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
RibavirinTablet, film coated500 mg/1OralZydus Pharmaceuticals Usa, Inc.2005-12-05Not applicableUs
RibavirinCapsule200 mg/1OralCadila Pharnmaceuticals2006-01-25Not applicableUs
RibavirinTablet, film coated600 mg/1OralRichmond Pharmaceuticals2008-06-01Not applicableUs
RibavirinTablet, coated200 mg/1OralTeva2005-12-052016-02-06Us
RibavirinCapsule200 mg/1OralSandoz2004-04-06Not applicableUs
RibavirinCapsule200 mg/1OralAv Kare, Inc.2014-01-172015-12-29Us
RibavirinTablet, film coated200 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
RibavirinTablet, film coated600 mg/1OralZydus Pharmaceuticals Usa, Inc.2005-12-05Not applicableUs
RibavirinTablet, film coated400 mg/1OralCadila Pharnmaceuticals2005-12-05Not applicableUs
RibavirinCapsule200 mg/1OralAmerincan Health Packaging2006-11-30Not applicableUs
RibavirinCapsule200 mg/1OralRichmond Pharmaceuticals2007-11-01Not applicableUs
RibavirinTablet, film coated200 mg/1OralAurobindo Pharma2009-09-17Not applicableUs
RibavirinTablet, film coated200 mg/1OralAmerincan Health Packaging2006-11-302015-12-29Us
RibavirinTablet, film coated200 mg/1OralRichmond Pharmaceuticals2008-06-01Not applicableUs
RibavirinCapsule200 mg/1OralZydus Pharmaceuticals Usa, Inc.2006-01-25Not applicableUs
RibavirinTablet, film coated500 mg/1OralCadila Pharnmaceuticals2005-12-05Not applicableUs
RibavirinTablet, film coated200 mg/1OralZydus Pharmaceuticals Usa, Inc.2005-12-05Not applicableUs
RibavirinTablet, film coated200 mg/1OralCadila Pharnmaceuticals2005-12-05Not applicableUs
Ribavirin MylanCapsule200 mgOralInternational Pharmaceutical Generics Ltd2010-06-10Not applicableEu
Ribavirin MylanCapsule200 mgOralInternational Pharmaceutical Generics Ltd2010-06-10Not applicableEu
Ribavirin MylanCapsule200 mgOralInternational Pharmaceutical Generics Ltd2010-06-10Not applicableEu
Ribavirin MylanCapsule200 mgOralInternational Pharmaceutical Generics Ltd2010-06-10Not applicableEu
Ribavirin MylanCapsule200 mgOralInternational Pharmaceutical Generics Ltd2010-06-10Not applicableEu
Ribavirin MylanCapsule200 mgOralInternational Pharmaceutical Generics Ltd2010-06-10Not applicableEu
Ribavirin MylanCapsule200 mgOralInternational Pharmaceutical Generics Ltd2010-06-10Not applicableEu
Ribavirin MylanCapsule200 mgOralInternational Pharmaceutical Generics Ltd2010-06-10Not applicableEu
Ribavirin MylanCapsule200 mgOralInternational Pharmaceutical Generics Ltd2010-06-10Not applicableEu
Ribavirin MylanCapsule200 mgOralInternational Pharmaceutical Generics Ltd2010-06-10Not applicableEu
Ribavirin MylanCapsule200 mgOralInternational Pharmaceutical Generics Ltd2010-06-10Not applicableEu
Ribavirin Teva Pharma B.V.Tablet, film coated200 mgOralTeva B.V.  2009-07-01Not applicableEu
Ribavirin Teva Pharma B.V.Tablet, film coated400 mgOralTeva B.V.  2009-07-01Not applicableEu
Ribavirin Teva Pharma B.V.Tablet, film coated200 mgOralTeva B.V.  2009-07-01Not applicableEu
Ribavirin Teva Pharma B.V.Tablet, film coated200 mgOralTeva B.V.  2009-07-01Not applicableEu
Ribavirin Teva Pharma B.V.Tablet, film coated400 mgOralTeva B.V.  2009-07-01Not applicableEu
Ribavirin Teva Pharma B.V.Tablet, film coated200 mgOralTeva B.V.  2009-07-01Not applicableEu
Ribavirin Teva Pharma B.V.Tablet, film coated400 mgOralTeva B.V.  2009-07-01Not applicableEu
Ribavirin Teva Pharma B.V.Tablet, film coated400 mgOralTeva B.V.  2009-07-01Not applicableEu
Ribavirin Teva Pharma B.V.Tablet, film coated200 mgOralTeva B.V.  2009-07-01Not applicableEu
Ribavirin Teva Pharma B.V.Tablet, film coated200 mgOralTeva B.V.  2009-07-01Not applicableEu
Ribavirin Teva Pharma B.V.Tablet, film coated400 mgOralTeva B.V.  2009-07-01Not applicableEu
Ribavirin Teva Pharma B.V.Tablet, film coated400 mgOralTeva B.V.  2009-07-01Not applicableEu
Ribavirin Teva Pharma B.V.Tablet, film coated200 mgOralTeva B.V.  2009-07-01Not applicableEu
Ribavirin Teva Pharma B.V.Tablet, film coated200 mgOralTeva B.V.  2009-07-01Not applicableEu
Ribavirin Teva Pharma B.V.Tablet, film coated400 mgOralTeva B.V.  2009-07-01Not applicableEu
Ribavirin Teva Pharma B.V.Tablet, film coated400 mgOralTeva B.V.  2009-07-01Not applicableEu
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ribavirin BiopartnersTablet, film coated200 mgOralBio Partners Gmb H2010-04-06Not applicableEu
Ribavirin BiopartnersTablet, film coated200 mgOralBio Partners Gmb H2010-04-06Not applicableEu
Ribavirin BiopartnersTablet, film coated200 mgOralBio Partners Gmb H2010-04-06Not applicableEu
Ribavirin BiopartnersTablet, film coated200 mgOralBio Partners Gmb H2010-04-06Not applicableEu
International Brands
NameCompany
RebretronNot Available
RibamideNot Available
VilonaValeant
ViramidIl Sung
VirazideGrossman
Brand mixtures
NameLabellerIngredients
Pegasys RbvHoffmann La Roche
PegetronMerck Ltd.
Rebetron Ready To Use Solution (albumin(human)free) (6000000 Iu/ml and 200mg Capsules)Schering Plough
Rebetron Solution (albumin (human) Free) (18 Miu Multi-dose Pen / 200mg Capsules)Schering Plough
Victrelis TripleMerck Ltd.
Salts
Name/CASStructureProperties
Ribavirin monophosphate
40925-28-8
Thumb
  • InChI Key: SDWIOXKHTFOULX-AFCXAGJDSA-N
  • Monoisotopic Mass: 324.047099924
  • Average Mass: 324.1846
DBSALT001876
Categories
UNII49717AWG6K
CAS number36791-04-5
WeightAverage: 244.2047
Monoisotopic: 244.080769514
Chemical FormulaC8H12N4O5
InChI KeyIWUCXVSUMQZMFG-AFCXAGJDSA-N
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
IUPAC Name
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide
SMILES
NC(=O)C1=NN(C=N1)[C@@H]1O[[email protected]](CO)[C@@H](O)[[email protected]]1O
Pharmacology
IndicationFor the treatment of chronic hepatitis C and for respiratory syncytial virus (RSV).
Structured Indications
Clinical Trials
PhaseStatusPurposeConditionsCount
0TerminatedTreatmentChronic Hepatitis C (CHC) / Genotype 1 / Relapses1
1CompletedNot AvailableChronic Hepatitis C (CHC) / Hemophilia1
1CompletedNot AvailableHealthy1
1CompletedNot AvailableHealthy Volunteers2
1CompletedTreatmentChronic Hepatitis C (CHC)1
1CompletedTreatmentChronic Hepatitis C Infection1
1CompletedTreatmentHCV (Genotype 1)1
1CompletedTreatmentHCV / Infection, Human Immunodeficiency Virus1
1CompletedTreatmentHepatic Insufficiency1
1CompletedTreatmentHepatitis C1
1CompletedTreatmentHepatitis C, Chronic2
1CompletedTreatmentInfection, Human Immunodeficiency Virus6
1RecruitingTreatmentHepatitis / HIV-1 Infections1
1TerminatedTreatmentHepatitis C1
1WithdrawnDiagnosticChronic Hepatitis C (CHC)1
1, 2CompletedTreatmentAcute Myeloid Leukaemias (AML)1
1, 2CompletedTreatmentFlu caused by Influenza1
1, 2CompletedTreatmentHepatitis C / HIV Disease1
1, 2CompletedTreatmentHepatitis C3
1, 2CompletedTreatmentHepatitis C / Infection, Human Immunodeficiency Virus1
1, 2RecruitingTreatmentMalignant Solid Tumours1
1, 2TerminatedTreatmentHepatitis C1
1, 2TerminatedTreatmentMetastatic Breast Cancer (MBC)1
2Active Not RecruitingTreatmentBone Marrow Transplant Infection / Cancers / Infection in Marrow Transplant Recipients / Infections, Respiratory Syncytial Virus / Leukaemia, Acute / Respiratory Syncytial Virus Pneumonia1
2Active Not RecruitingTreatmentChronic Hepatitis C (CHC)3
2Active Not RecruitingTreatmentChronic Hepatitis C (CHC) / HCV / Hepatitis C Virus (HCV)1
2Active Not RecruitingTreatmentChronic Hepatitis C (CHC) / Hepatitis C (HCV) / Hepatitis C Genotype 11
2Active Not RecruitingTreatmentChronic Hepatitis C Infection2
2Active Not RecruitingTreatmentFibrosis / Hepatitis C, Chronic1
2Active Not RecruitingTreatmentHCV Infections / Liver Cirrhosis, Experimental1
2Active Not RecruitingTreatmentHepatitis C5
2Active Not RecruitingTreatmentHepatitis C Virus Genotype 4 Infection1
2Active Not RecruitingTreatmentHepatitis C Virus Infection3
2Active Not RecruitingTreatmentHepatitis C, Chronic2
2Active Not RecruitingTreatmentHepatitis C, Liver Disease1
2CompletedNot AvailableHepatitis C1
2CompletedTreatmentAcute Myelocytic Leukemia1
2CompletedTreatmentAnemias / Hepatitis C / HIV Disease1
2CompletedTreatmentAnemias / Hepatitis C1
2CompletedTreatmentChronic HCV Infection4
2CompletedTreatmentChronic Hepatitis C (CHC)26
2CompletedTreatmentChronic Hepatitis C (CHC) / Chronic Hepatitis C Infection1
2CompletedTreatmentChronic Hepatitis C (CHC) / Hepatitis C (HCV) / Hepatitis C Genotype 11
2CompletedTreatmentChronic Hepatitis C (CHC) / Hepatitis C (HCV) / Hepatitis C Genotype 1a1
2CompletedTreatmentChronic Hepatitis C (CHC) / Hepatitis C Virus (HCV)1
2CompletedTreatmentChronic Hepatitis C (CHC) / Hepatitis C Virus (HCV) Infection1
2CompletedTreatmentChronic Hepatitis C (CHC) / Compensated liver disease / Hepatitis C Virus (HCV)1
2CompletedTreatmentChronic Hepatitis C (CHC) / Hepatitis C / Hepatitis C, Chronic / Liver Cirrhosis1
2CompletedTreatmentChronic Hepatitis C (CHC) / Infection, Human Immunodeficiency Virus1
2CompletedTreatmentChronic Hepatitis C Infection5
2CompletedTreatmentChronic Hepatitis C Infection / HCV / Hepatitis C / Hepatitis C Genotype 12
2CompletedTreatmentChronic Hepatitis C Infection / Hepatitis C / Hepatitis C Virus (HCV)1
2CompletedTreatmentChronic Hepatitis C Virus4
2CompletedTreatmentChronic Hepatitis C Virus Infection1
2CompletedTreatmentFlu caused by Influenza1
2CompletedTreatmentGenotype 1 Chronic Hepatitis C1
2CompletedTreatmentHCV Coinfection / HIV-1 Infections1
2CompletedTreatmentHCV Infections4
2CompletedTreatmentHCV Infections / Hepatitis C / Infection, Human Immunodeficiency Virus1
2CompletedTreatmentHIV-1 and Hepatitis C Co-Infection1
2CompletedTreatmentHemophilia / Hepatitis C / Infection, Human Immunodeficiency Virus1
2CompletedTreatmentHepatitis C27
2CompletedTreatmentHepatitis C Infection4
2CompletedTreatmentHepatitis C Infection / Infection, Human Immunodeficiency Virus1
2CompletedTreatmentHepatitis C Virus (HCV)11
2CompletedTreatmentHepatitis C Virus Infection2
2CompletedTreatmentHepatitis C, Chronic40
2CompletedTreatmentHepatitis C, Chronic / Infection, Human Immunodeficiency Virus1
2CompletedTreatmentHepatitis C, Chronic / Infection, Human Immunodeficiency Virus / Treatment Failure1
2CompletedTreatmentHepatitis C / Hepatocellular Carcinomas1
2CompletedTreatmentHepatitis C / Infection, Human Immunodeficiency Virus4
2CompletedTreatmentHepatitis C / Infection, Human Immunodeficiency Virus / Liver Diseases1
2CompletedTreatmentHepatitis C / Liver Cirrhosis / Portal Hypertension / With or Without Liver Decompensation1
2CompletedTreatmentHepatitis C / Pharmacokinetics1
2CompletedTreatmentHepatitis C / Thalassemias1
2CompletedTreatmentHepatitis / Hepatitis C1
2CompletedTreatmentHepatitits C1
2CompletedTreatmentPost Liver Transplant / Recurrent Chronic Hepatitis C Virus1
2Enrolling by InvitationTreatmentHemorrhagic Fever With Renal Syndrome2
2Not Yet RecruitingTreatmentChronic Hepatitis C (CHC) / Hepatitis C (HCV) / Hepatitis C Genotype 1 / Hepatitis C Viral Infection1
2Not Yet RecruitingTreatmentHepatitis C1
2Not Yet RecruitingTreatmentHepatitis C, Chronic1
2RecruitingTreatmentAcute Myeloid Leukaemias (AML)1
2RecruitingTreatmentAcute on Chronic Hepatic Failure / Hepatitis E Infection / Liver Failure1
2RecruitingTreatmentChronic Hepatitis C (CHC)1
2RecruitingTreatmentChronic Hepatitis C (CHC) / Hepatitis C (HCV) / Hepatitis C Genotype 4 / Hepatitis C Viral Infection1
2RecruitingTreatmentChronic Hepatitis C (CHC) / Hepatitis C Virus (HCV)1
2RecruitingTreatmentChronic Hepatitis C Infection1
2RecruitingTreatmentChronic Hepatitis C Virus Infection1
2RecruitingTreatmentDengue Fever / Viral Haemorrhagic Fever1
2RecruitingTreatmentDigestive System Diseases / Flaviviridae Infections / Hepatitis / Hepatitis C / Hepatitis, Viral, Human / Liver Diseases / RNA Virus Infections / Virus Diseases1
2RecruitingTreatmentFlu caused by Influenza1
2RecruitingTreatmentHCV Infections1
2RecruitingTreatmentHepatitis C / HIV-1 Infections1
2RecruitingTreatmentHepatitis C1
2RecruitingTreatmentHepatitis C Virus Infection2
2RecruitingTreatmentHepatitis C, Chronic1
2RecruitingTreatmentHepatitis C / Infection, Human Immunodeficiency Virus1
2RecruitingTreatmentHepatitis C / Liver Cirrhosis1
2RecruitingTreatmentInfection, Human Immunodeficiency Virus1
2RecruitingTreatmentJapanese Encephalitis1
2SuspendedTreatmentHepatitis C Infection / Thrombocytopenias1
2TerminatedTreatmentChronic Hepatitis C (CHC)2
2TerminatedTreatmentChronic Hepatitis C Virus Infection1
2TerminatedTreatmentHepatitis C3
2TerminatedTreatmentHepatitis C, Chronic1
2WithdrawnTreatmentChronic Genotype 1 Hepatitis C Virus Infection1
2WithdrawnTreatmentChronic Hepatitis C Virus Genotype 11
2WithdrawnTreatmentHepatitis B / Hepatitis C / Infection, Human Immunodeficiency Virus1
2WithdrawnTreatmentHepatitis C1
2WithdrawnTreatmentHepatitis C Virus (HCV)1
2WithdrawnTreatmentHepatitis C, Chronic1
2WithdrawnTreatmentHepatitis C / Hepatitis C Virus (HCV)1
2, 3Active Not RecruitingTreatmentChronic Hepatitis C (CHC)1
2, 3CompletedNot AvailableLiver Cirrhosis, Experimental1
2, 3CompletedTreatmentChronic Hepatitis C (CHC)2
2, 3CompletedTreatmentFibrosis, Liver / Hepatitis C, Chronic1
2, 3CompletedTreatmentHepatitis C2
2, 3CompletedTreatmentHepatitis C Virus (HCV) / Infection, Human Immunodeficiency Virus / Liver Cirrhosis1
2, 3CompletedTreatmentHepatitis / Hepatitis C1
2, 3RecruitingTreatmentChronic Hepatitis C (CHC) / Insulin Resistance1
2, 3TerminatedNot AvailableHepacivirus / Hepatitis C, Chronic1
2, 3WithdrawnTreatmentHepatitis C1
2, 3WithdrawnTreatmentHepatitis C, Chronic1
3Active Not RecruitingTreatmentChronic Hepatitis C (CHC)1
3Active Not RecruitingTreatmentChronic Hepatitis C (CHC) / Cirrhosis, Decompensated / Hepatitis C Virus (HCV)1
3Active Not RecruitingTreatmentChronic Hepatitis C (CHC) / Compensated Cirrhosis and Non-cirrhotics / Hepatitis C Virus Infection / Infection, Human Immunodeficiency Virus1
3Active Not RecruitingTreatmentChronic Hepatitis C (CHC) / Hepatitis C Virus (HCV) / Liver Cirrhosis1
3Active Not RecruitingTreatmentChronic Hepatitis C Infection2
3Active Not RecruitingTreatmentChronic Hepatitis C Virus1
3Active Not RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection Genotype 11
3Active Not RecruitingTreatmentGenotype 4 / HCV / Hepatitis C Infection1
3Active Not RecruitingTreatmentHepatitis C3
3Active Not RecruitingTreatmentHepatitis C Infection1
3Active Not RecruitingTreatmentHepatitis C Virus (HCV)1
3Active Not RecruitingTreatmentHepatitis C Virus Infection1
3Active Not RecruitingTreatmentHepatitis C / Liver Cirrhosis1
3CompletedNot AvailableHepatitis B1
3CompletedDiagnosticHepatitis C / Transplantation, Liver1
3CompletedHealth Services ResearchHIV Disease1
3CompletedPreventionChronic Hepatitis C (CHC) / Fibrosis, Liver / Hepatic Cirrhosis / Liver Cirrhosis1
3CompletedPreventionDepression1
3CompletedSupportive CareCancers1
3CompletedSupportive CareInfection NOS1
3CompletedTreatmentChronic HCV Infection3
3CompletedTreatmentChronic Hepatitis C (CHC)21
3CompletedTreatmentChronic Hepatitis C (CHC) / Compensated liver disease / End-Stage Renal Disease (ESRD) / Hepatitis C Virus (HCV) / Severe Renal Impairment1
3CompletedTreatmentChronic Hepatitis C (CHC) / Fibrosis / Hemolytic Anemia1
3CompletedTreatmentChronic Hepatitis C (CHC) / Hepatitis C (HCV) / Hepatitis C Genotype 1a1
3CompletedTreatmentChronic Hepatitis C (CHC) / Human Immunodeficiency Virus (HIV)1
3CompletedTreatmentChronic Hepatitis C (CHC) / Liver Cirrhosis1
3CompletedTreatmentChronic Hepatitis C Infection9
3CompletedTreatmentChronic Hepatitis C Infection / Compensated liver disease1
3CompletedTreatmentChronic Hepatitis C Virus3
3CompletedTreatmentChronic Hepatitis C Virus (HCV Infection Genotype 1)1
3CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
3CompletedTreatmentCoinfection / Hepatitis C / Infection, Human Immunodeficiency Virus1
3CompletedTreatmentFibrosis / Hepatitis / Hepatitis C, Chronic / Liver Cirrhosis1
3CompletedTreatmentGenotype 1 Chronic Hepatitis C1
3CompletedTreatmentGenotype 1 Chronic Hepatitis C / Treatment Naive1
3CompletedTreatmentHCV Infections / Hepatitis C, Chronic1
3CompletedTreatmentHepatitis C Virus (HCV) / HIV Disease1
3CompletedTreatmentHepatitis C27
3CompletedTreatmentHepatitis C Infection1
3CompletedTreatmentHepatitis C Virus (HCV)7
3CompletedTreatmentHepatitis C Virus Genotype-11
3CompletedTreatmentHepatitis C Virus Infection5
3CompletedTreatmentHepatitis C, Chronic30
3CompletedTreatmentHepatitis C, Chronic / Infection NOS1
3CompletedTreatmentHepatitis C, Chronic / Infection, Human Immunodeficiency Virus1
3CompletedTreatmentHepatitis C, Chronic / Liver Cirrhosis1
3CompletedTreatmentHepatitis C, Genotype 11
3CompletedTreatmentHepatitis C / Human Immunodeficiency Virus (HIV)1
3CompletedTreatmentHepatitis C / Infection, Human Immunodeficiency Virus1
3CompletedTreatmentHepatitis / Opiate Dependence1
3CompletedTreatmentGenotype 1 chronic hepatitis C infection1
3Not Yet RecruitingTreatmentHepatitis C / Liver Cirrhosis1
3RecruitingNot AvailableHepatitis C1
3RecruitingTreatmentChronic Hepatitis C (CHC)2
3RecruitingTreatmentChronic Hepatitis C Infection2
3RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection Genotype 11
3RecruitingTreatmentGenotype 4 Chronic Hepatitis C Infection1
3RecruitingTreatmentHepatitis C Virus Infection1
3RecruitingTreatmentHepatitis C, Chronic1
3RecruitingTreatmentHepatitis C / Infection, Human Immunodeficiency Virus2
3TerminatedTreatmentChronic Hepatitis C (CHC)3
3TerminatedTreatmentHepatitis C1
3TerminatedTreatmentHepatitis C, Chronic3
3TerminatedTreatmentHepatitis C, Chronic / Liver Cirrhosis1
3TerminatedTreatmentInfection NOS1
3WithdrawnTreatmentChronic Hepatitis C (CHC)4
3WithdrawnTreatmentHepatitis C1
3WithdrawnTreatmentHepatitis C Virus (HCV)1
3WithdrawnTreatmentHepatitis C, Chronic3
4Active Not RecruitingNot AvailableHepatitis C Infection / HIV Disease1
4Active Not RecruitingTreatmentChronic Hepatitis C (CHC) / Hepatocellular Carcinomas1
4Active Not RecruitingTreatmentHepatitis C / HIV Disease1
4Active Not RecruitingTreatmentHepatitis C1
4Active Not RecruitingTreatmentHepatitis C Virus (HCV)1
4Active Not RecruitingTreatmentHepatitis C, Chronic1
4CompletedNot AvailableHepatitis C, Chronic1
4CompletedNot AvailableHepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted1
4CompletedBasic ScienceHepatitis C, Chronic / Liver Diseases / Virus Diseases1
4CompletedPreventionHepatitis C, Chronic1
4CompletedPreventionHepatitis C / Liver Transplant1
4CompletedSupportive CareChronic Hepatitis C (CHC)1
4CompletedTreatmentAcute Hepatitis C1
4CompletedTreatmentAlcoholism / Drug Abuse / Hepatitis C / Liver Diseases1
4CompletedTreatmentAnemias1
4CompletedTreatmentAntiviral Agents / Chronic Liver Diseases (CLD) / Hepatitis C Virus (HCV) / Therapeutic Uses / Viral Hepatitis1
4CompletedTreatmentAsian Americans / Chronic Hepatitis C (CHC) / Novel Genotypes / Treatments1
4CompletedTreatmentChronic Hepatitis C (CHC)8
4CompletedTreatmentChronic Hepatitis C (CHC) / Genotyping1
4CompletedTreatmentChronic Hepatitis C (CHC) / Hemodialysis1
4CompletedTreatmentChronic Hepatitis C, Genotype 11
4CompletedTreatmentDiabetes Mellitus Type 2 / Hepatitis C, Chronic1
4CompletedTreatmentFatty Liver / Hepatitis C1
4CompletedTreatmentHematological Malignancy1
4CompletedTreatmentHepatitis C14
4CompletedTreatmentHepatitis C Virus (HCV)1
4CompletedTreatmentHepatitis C Virus (HCV) / Infection, Human Immunodeficiency Virus1
4CompletedTreatmentHepatitis C Virus Infection1
4CompletedTreatmentHepatitis C, Chronic28
4CompletedTreatmentHepatitis C, Chronic / Infection, Human Immunodeficiency Virus1
4CompletedTreatmentHepatitis C / Human Immunodeficiency Virus (HIV) / Infection, Human Immunodeficiency Virus1
4CompletedTreatmentHepatitis C / Infection, Human Immunodeficiency Virus1
4Not Yet RecruitingTreatmentChronic Hepatitis C (CHC) / End Stage Renal Disease (ESRD)1
4Not Yet RecruitingTreatmentHepatitis C1
4Not Yet RecruitingTreatmentHepatitis C, Acute1
4RecruitingHealth Services ResearchHemoglobinopathies1
4RecruitingTreatmentChronic Hepatitis C (CHC)2
4RecruitingTreatmentHepatitis C / HIV Disease / HIV-HCV Coinfection1
4RecruitingTreatmentHepatitis C, Chronic / HIV Disease1
4RecruitingTreatmentHandfoot-mouth Disease1
4RecruitingTreatmentHepatitis C3
4RecruitingTreatmentHepatitis C Infection / Infection, Human Immunodeficiency Virus1
4RecruitingTreatmentHepatitis E1
4RecruitingTreatmentLiver Diseases1
4TerminatedTreatmentChronic Hepatitis C (CHC)1
4TerminatedTreatmentHepatitis / HIV/AIDS1
4TerminatedTreatmentHepacivirus / Hepatitis C, Chronic / Infection, Human Immunodeficiency Virus1
4TerminatedTreatmentHepatitis C4
4TerminatedTreatmentHepatitis C, Chronic4
4TerminatedTreatmentHepatitis C, Chronic / Insulin Resistance1
4WithdrawnTreatmentHepatitis C2
Not AvailableActive Not RecruitingNot AvailableHepatitis C1
Not AvailableActive Not RecruitingNot AvailableHepatitis C Virus Infection1
Not AvailableActive Not RecruitingNot AvailableHepatitis C, Chronic / Personality Disorders in Prison1
Not AvailableActive Not RecruitingTreatmentHEAD & NECK Cancer1
Not AvailableApproved for MarketingNot AvailablePost-transplant Hepatitis C1
Not AvailableCompletedNot AvailableChronic Hepatitis C (CHC)3
Not AvailableCompletedNot AvailableChronic Hepatitis C (CHC) / Hepatitis C1
Not AvailableCompletedNot AvailableChronic Hepatitis C (CHC) / Hepatitis C / Infection, Human Immunodeficiency Virus1
Not AvailableCompletedNot AvailableCognition Disorders / Fatigue Syndrome, Chronic / Hepatitis C, Chronic / Major Depressive Disorder (MDD)1
Not AvailableCompletedNot AvailableGenotype 1 / HCV-1 / Hepatitis C, Chronic1
Not AvailableCompletedNot AvailableHepacivirus / Hepatitis C, Chronic4
Not AvailableCompletedNot AvailableHepatitis C3
Not AvailableCompletedNot AvailableHepatitis C Virus (HCV) / Hepatitis C, Chronic1
Not AvailableCompletedNot AvailableHepatitis C, Chronic8
Not AvailableCompletedNot AvailableHepatitis C, Chronic / Substance Abuse, Intravenous1
Not AvailableCompletedNot AvailableHepatitis C / Hepatitis C, Chronic11
Not AvailableCompletedNot AvailableMelanoma1
Not AvailableCompletedBasic ScienceChronic Hepatitis C (CHC) / Human Immunodeficiency Virus (HIV)1
Not AvailableCompletedBasic ScienceChronic Hepatitis C Infection1
Not AvailableCompletedTreatmentChronic Hepatitis C (CHC)1
Not AvailableCompletedTreatmentChronic Hepatitis C (CHC) / Insulin Resistance1
Not AvailableCompletedTreatmentHantavirus pulmonary infection1
Not AvailableCompletedTreatmentHepatitis C Virus (HCV)1
Not AvailableCompletedTreatmentHepatitis C Virus Infection1
Not AvailableCompletedTreatmentHepatitis C, Chronic1
Not AvailableCompletedTreatmentHepatitis C / Infection, Human Immunodeficiency Virus2
Not AvailableNo Longer AvailableNot AvailableChronic Hepatitis C (CHC)1
Not AvailableNot Yet RecruitingTreatmentChronic Hepatitis C (CHC)1
Not AvailableNot Yet RecruitingTreatmentHepatitis C1
Not AvailableNot Yet RecruitingTreatmentViral Hemorrhagic Fevers1
Not AvailableRecruitingNot AvailableChronic Hepatitis C (CHC)1
Not AvailableRecruitingBasic ScienceChronic HCV Infection / Nonalcoholic Steatohepatitis1
Not AvailableRecruitingScreeningHepatitis C, Chronic1
Not AvailableRecruitingTreatmentAutoimmune Diseases / Hepatitis C / Lichen Planus (LP) / Vasculitis1
Not AvailableRecruitingTreatmentHepatitis C / Liver Cirrhosis1
Not AvailableRecruitingTreatmentHuman Papillomavirus (HPV)-Related Malignancies / Recurrent/Metastatic (R/M) Human Papillomavirus (HPV)-Related Malignancies1
Not AvailableTerminatedNot AvailableChronic Hepatitis C (CHC)1
Not AvailableTerminatedNot AvailableHepacivirus / Hepatitis C, Chronic1
Not AvailableTerminatedNot AvailableHepatitis C, Chronic1
Not AvailableTerminatedNot AvailableHepatitis C / Hepatitis C, Chronic3
Not AvailableTerminatedTreatmentChronic Hepatitis C (CHC)1
Not AvailableTerminatedTreatmentInfection, Human Immunodeficiency Virus1
Not AvailableWithdrawnNot AvailableHepatitis C / Hepatitis C, Chronic1
Not AvailableWithdrawnTreatmentEnd Stage Renal Disease (ESRD) / Hepatitis C Infection1
PharmacodynamicsRibavirin is an anti-viral drug active against a number of DNA and RNA viruses. It is a member of the nucleoside antimetabolite drugs that interfere with duplication of the viral genetic material. The drug inhibits the activity of the enzyme RNA dependent RNA polymerase, due to it's resemblence to building blocks of the RNA molecules. The oral form is used in the treatment of hepatitis C, in combination with interferon drugs. The aerosol form is used to treat respiratory syncytial virus-related diseases in children. The primary serious adverse effect of ribavirin is hemolytic anemia, which may worsen preexisting cardiac disease.
Mechanism of actionRibavirin is readily phosphorylated intracellularly by adenosine kinase to ribavirin mono-, di-, and triphosphate metabolites. Ribavirin triphosphate (RTP) is a potent competitive inhibitor of inosine monophosphate (IMP) dehydrogenase, viral RNA polymerase and messenger RNA (mRNA) guanylyltransferase (viral) and can be incorporated into RNA in RNA viral species.. Guanylyltranserase inhibition stops the capping of mRNA. These diverse effects result in a marked reduction of intracellular guanosine triphosphate (GTP) pools and inhibition of viral RNA and protein synthesis. Ribavirin is also incorporated into the viral genome causing lethal mutagenesis and a subsequent decrease in specific viral infectivity.
TargetKindPharmacological actionActionsOrganismUniProt ID
Inosine-5'-monophosphate dehydrogenase 1Proteinyes
inhibitor
HumanP20839 details
Inosine-5'-monophosphate dehydrogenase 2ProteinunknownNot AvailableHumanP12268 details
Adenosine kinaseProteinyes
activator
HumanP55263 details
RNA-directed RNA polymerase LProteinyes
antagonist
HPIV-2P26676 details
RNA-directed RNA polymerase catalytic subunitProteinunknown
inhibitor
Influenza A virus (strain A/Beijing/11/1956 H1N1)P16502 details
DNANucleotideunknown
incorporation into and destabilization
Humannot applicabledetails
Cytosolic purine 5'-nucleotidaseProteinunknown
inducer
HumanP49902 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1Proteinunknown
inhibitor
HumanP22413 details
Genome polyproteinProteinunknownNot AvailableDENV-2P12823 details
Related Articles
AbsorptionRapidly and extensively absorbed following oral administration. However, due to first-pass metabolism, the absolute bioavailability averages 64%.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic. Results of in vitro studies using both human and rat liver microsome preparations indicated little or no cytochrome P450 enzyme-mediated metabolism of ribavirin, with minimal potential for P450 enzyme-based drug interactions. Ribavirin has two pathways of metabolism: (1) a reversible phosphorylation pathway in nucleated cells; and (2) a degradative pathway involving deribosylation and amide hydrolysis to yield a triazole carboxylic acid metabolite.

Route of eliminationNot Available
Half life9.5 hours
Clearance
  • Apparent cl=26 L/h [A single oral dose]
ToxicitySide effects include "flu-like" symptoms, such as headache, fatigue, myalgia, and fever. The LD50 in mice is 2 g/kg orally and is associated with hypoactivity and gastrointestinal symptoms (estimated human equivalent dose of 0.17 g/kg, based on body surface area conversion).
Affected organisms
  • Hepatitis C virus, RSV and other RNA/DNA viruses
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbacavirRibavirin may increase the hepatotoxic activities of Abacavir.Approved, Investigational
AzathioprineThe serum concentration of the active metabolites of Azathioprine can be increased when Azathioprine is used in combination with Ribavirin.Approved
DidanosineThe risk or severity of adverse effects can be increased when Ribavirin is combined with Didanosine.Approved
EmtricitabineRibavirin may increase the hepatotoxic activities of Emtricitabine.Approved, Investigational
EntecavirRibavirin may increase the hepatotoxic activities of Entecavir.Approved, Investigational
Interferon Alfa-2a, RecombinantThe risk or severity of adverse effects can be increased when Interferon Alfa-2a, Recombinant is combined with Ribavirin.Approved
Interferon Alfa-2b, RecombinantThe risk or severity of adverse effects can be increased when Interferon Alfa-2b, Recombinant is combined with Ribavirin.Approved
Interferon alfa-n3The risk or severity of adverse effects can be increased when Interferon alfa-n3 is combined with Ribavirin.Approved, Investigational
Interferon alfacon-1The risk or severity of adverse effects can be increased when Interferon alfacon-1 is combined with Ribavirin.Approved
LamivudineRibavirin may increase the hepatotoxic activities of Lamivudine.Approved, Investigational
Peginterferon alfa-2aThe risk or severity of adverse effects can be increased when Peginterferon alfa-2a is combined with Ribavirin.Approved, Investigational
Peginterferon alfa-2bThe risk or severity of adverse effects can be increased when Peginterferon alfa-2b is combined with Ribavirin.Approved
StavudineRibavirin may increase the hepatotoxic activities of Stavudine.Approved, Investigational
ZalcitabineRibavirin may increase the hepatotoxic activities of Zalcitabine.Approved
ZidovudineThe risk or severity of adverse effects can be increased when Zidovudine is combined with Ribavirin.Approved
Food InteractionsNot Available
References
Synthesis Reference

DrugSyn.org

US3798209
General References
  1. Sidwell RW, Bailey KW, Wong MH, Barnard DL, Smee DF: In vitro and in vivo influenza virus-inhibitory effects of viramidine. Antiviral Res. 2005 Oct;68(1):10-7. [PubMed:16087250 ]
  2. Sidwell RW, Huffman JH, Khare GP, Allen LB, Witkowski JT, Robins RK: Broad-spectrum antiviral activity of Virazole: 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide. Science. 1972 Aug 25;177(4050):705-6. [PubMed:4340949 ]
  3. Alvarez D, Dieterich DT, Brau N, Moorehead L, Ball L, Sulkowski MS: Zidovudine use but not weight-based ribavirin dosing impacts anaemia during HCV treatment in HIV-infected persons. J Viral Hepat. 2006 Oct;13(10):683-9. [PubMed:16970600 ]
  4. Bani-Sadr F, Carrat F, Pol S, Hor R, Rosenthal E, Goujard C, Morand P, Lunel-Fabiani F, Salmon-Ceron D, Piroth L, Pialoux G, Bentata M, Cacoub P, Perronne C: Risk factors for symptomatic mitochondrial toxicity in HIV/hepatitis C virus-coinfected patients during interferon plus ribavirin-based therapy. J Acquir Immune Defic Syndr. 2005 Sep 1;40(1):47-52. [PubMed:16123681 ]
External Links
ATC CodesJ05AB04
AHFS Codes
  • 08:18.32
PDB Entries
FDA labelDownload (2.17 MB)
MSDSDownload (39.3 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9852
Blood Brain Barrier+0.9381
Caco-2 permeable-0.7742
P-glycoprotein substrateNon-substrate0.7715
P-glycoprotein inhibitor INon-inhibitor0.9507
P-glycoprotein inhibitor IINon-inhibitor0.964
Renal organic cation transporterNon-inhibitor0.9574
CYP450 2C9 substrateNon-substrate0.8329
CYP450 2D6 substrateNon-substrate0.8426
CYP450 3A4 substrateNon-substrate0.6011
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9462
CYP450 2D6 inhibitorNon-inhibitor0.9442
CYP450 2C19 inhibitorNon-inhibitor0.9095
CYP450 3A4 inhibitorNon-inhibitor0.9535
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9845
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9025
BiodegradationNot ready biodegradable0.7406
Rat acute toxicity1.9876 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9948
hERG inhibition (predictor II)Non-inhibitor0.919
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Schering plough research institute
  • Three rivers pharmaceuticals llc
  • Aurobindo pharma ltd
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Zydus pharmaceuticals usa inc
  • Valeant pharmaceuticals international
  • Schering corp
  • Hoffmann la roche inc
Packagers
Dosage forms
FormRouteStrength
Tablet, film coatedOral200 mg/1
TabletOral200 mg
TabletOral400 mg
TabletOral600 mg
Kit
Tablet, film coatedOral400 mg/1
Tablet, film coatedOral600 mg/1
Solution; tabletOral; Subcutaneous
Capsule; powder, for solutionOral; Subcutaneous
CapsuleOral200 mg
LiquidOral40 mg/mL
SolutionOral40 mg/ml
Capsule; kit; liquidOral; Subcutaneous
TabletOral200 mg/1
TabletOral400 mg/1
TabletOral600 mg/1
CapsuleOral200 mg/1
Tablet, coatedOral200 mg/1
Tablet, film coatedOral500 mg/1
Tablet, film coatedOral200 mg
Tablet, film coatedOral400 mg
Aerosol; powder, for solutionRespiratory (inhalation)6 g
Powder, for solutionRespiratory (inhalation)6 g/1
Prices
Unit descriptionCostUnit
Virazole 6 gm vial4512.21USD vial
Ribatab 600 mg tablet32.01USD tablet
Ribasphere 600 mg tablet24.88USD tablet
Ribavirin 600 mg tablet24.88USD tablet
Ribatab 400 mg tablet21.34USD tablet
Ribavirin 500 mg tablet20.74USD tablet
Ribasphere 400 mg tablet16.59USD tablet
Ribavirin 400 mg tablet16.59USD tablet
Copegus 200 mg tablet15.19USD tablet
Rebetol 200 mg capsule10.81USD capsule
Ribasphere 200 mg capsule10.33USD capsule
Ribavirin 200 mg capsule10.33USD capsule
Ribasphere 200 mg tablet8.29USD tablet
Ribavirin 200 mg tablet8.29USD tablet
Ribavirin powder3.21USD g
Rebetol 40 mg/ml Solution2.42USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2287056 No2000-08-152018-12-21Canada
CA2365412 No2002-09-172018-12-21Canada
US6150337 No1997-11-212017-11-21Us
US6172046 Yes1998-03-212018-03-21Us
US6177074 Yes1997-05-012017-05-01Us
US6461605 Yes1997-05-012017-05-01Us
US6472373 Yes1998-03-212018-03-21Us
US6524570 Yes1997-05-012017-05-01Us
US6790837 Yes2003-10-052023-10-05Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point174-176 °CNot Available
water solubility142 mg/mL (max, at 25 °C)Not Available
logP-1.85BIOBYTE (1995)
Predicted Properties
PropertyValueSource
Water Solubility33.2 mg/mLALOGPS
logP-1.9ALOGPS
logP-2.8ChemAxon
logS-0.87ALOGPS
pKa (Strongest Acidic)11.88ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area143.72 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity64.57 m3·mol-1ChemAxon
Polarizability22.18 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as triazole ribonucleosides and ribonucleotides. These are nucleoside derivatives containing a ribose (or deoxyribose) moiety which is N-glycosylated to a triazole. Nucleotides have a phosphate group linked to the C5 carbon of the ribose (or deoxyribose) moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassTriazole ribonucleosides and ribonucleotides
Direct ParentTriazole ribonucleosides and ribonucleotides
Alternative Parents
Substituents
  • N-ribosyl-1,2,4-triazole
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • 2-heteroaryl carboxamide
  • Monosaccharide
  • Azole
  • Oxolane
  • Triazole
  • 1,2,4-triazole
  • Heteroaromatic compound
  • Carboxamide group
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Rna binding
Specific Function:
Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in t...
Gene Name:
IMPDH1
Uniprot ID:
P20839
Molecular Weight:
55405.365 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Gish RG: Treating HCV with ribavirin analogues and ribavirin-like molecules. J Antimicrob Chemother. 2006 Jan;57(1):8-13. Epub 2005 Nov 17. [PubMed:16293677 ]
  3. McHutchison JG, Shiffman ML, Cheung RC, Gordon SC, Wright TL, Pottage JC Jr, McNair L, Ette E, Moseley S, Alam J: A randomized, double-blind, placebo-controlled dose-escalation trial of merimepodib (VX-497) and interferon-alpha in previously untreated patients with chronic hepatitis C. Antivir Ther. 2005;10(5):635-43. [PubMed:16152757 ]
  4. Leyssen P, De Clercq E, Neyts J: The anti-yellow fever virus activity of ribavirin is independent of error-prone replication. Mol Pharmacol. 2006 Apr;69(4):1461-7. Epub 2006 Jan 18. [PubMed:16421290 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Rna binding
Specific Function:
Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in t...
Gene Name:
IMPDH2
Uniprot ID:
P12268
Molecular Weight:
55804.495 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
activator
General Function:
Poly(a) rna binding
Specific Function:
ATP dependent phosphorylation of adenosine and other related nucleoside analogs to monophosphate derivatives. Serves as a potential regulator of concentrations of extracellular adenosine and intracellular adenine nucleotides.
Gene Name:
ADK
Uniprot ID:
P55263
Molecular Weight:
40545.075 Da
References
  1. Wu JZ, Larson G, Walker H, Shim JH, Hong Z: Phosphorylation of ribavirin and viramidine by adenosine kinase and cytosolic 5'-nucleotidase II: Implications for ribavirin metabolism in erythrocytes. Antimicrob Agents Chemother. 2005 Jun;49(6):2164-71. [PubMed:15917509 ]
  2. Kumarapperuma SC, Sun Y, Jeselnik M, Chung K, Parker WB, Jonsson CB, Arterburn JB: Structural effects on the phosphorylation of 3-substituted 1-beta-D-ribofuranosyl-1,2,4-triazoles by human adenosine kinase. Bioorg Med Chem Lett. 2007 Jun 1;17(11):3203-7. Epub 2007 Mar 12. [PubMed:17379518 ]
Kind
Protein
Organism
HPIV-2
Pharmacological action
yes
Actions
antagonist
General Function:
Rna-directed rna polymerase activity
Specific Function:
Displays RNA-directed RNA polymerase, mRNA guanylyl transferase, mRNA (guanine-N(7)-)-methyltransferase and poly(A) synthetase activities. The viral mRNA guanylyl transferase displays a different biochemical reaction than the cellular enzyme. The template is composed of the viral RNA tightly encapsidated by the nucleoprotein (N). Functions either as transcriptase or as replicase. The transcript...
Gene Name:
L
Uniprot ID:
P26676
Molecular Weight:
256380.115 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Influenza A virus (strain A/Beijing/11/1956 H1N1)
Pharmacological action
unknown
Actions
inhibitor
General Function:
Rna-directed rna polymerase activity
Specific Function:
RNA-dependent RNA polymerase which is responsible for replication and transcription of virus RNA segments. The transcription of viral mRNAs occurs by a unique mechanism called cap-snatching. 5' methylated caps of cellular mRNAs are cleaved after 10-13 nucleotides by PA. In turn, these short capped RNAs are used as primers by PB1 for transcription of viral mRNAs. During virus replication, PB1 in...
Gene Name:
PB1
Uniprot ID:
P16502
Molecular Weight:
86534.5 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Bougie I, Bisaillon M: Initial binding of the broad spectrum antiviral nucleoside ribavirin to the hepatitis C virus RNA polymerase. J Biol Chem. 2003 Dec 26;278(52):52471-8. Epub 2003 Oct 16. [PubMed:14563844 ]
6. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
unknown
Actions
incorporation into and destabilization
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Ren FY, Jin H, Piao XX, Piao FS: Ribavirin and IFN-alpha combination therapy induces CD4+ T-cell proliferation and Th1 cytokine secretion in patients with chronic hepatitis B. World J Gastroenterol. 2007 Nov 7;13(41):5440-5. [PubMed:17907286 ]
  4. Crotty S, Cameron C, Andino R: Ribavirin's antiviral mechanism of action: lethal mutagenesis? J Mol Med (Berl). 2002 Feb;80(2):86-95. Epub 2001 Dec 4. [PubMed:11907645 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Nucleotide binding
Specific Function:
May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:
NT5C2
Uniprot ID:
P49902
Molecular Weight:
64969.2 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Zinc ion binding
Specific Function:
By generating PPi, plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. PPi inhibits mineralization by binding to nascent hydroxyapatite (HA) crystals, thereby preventing further growth of these crystals. Preferentially hydrolyzes ATP, but can also hydrolyze other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their c...
Gene Name:
ENPP1
Uniprot ID:
P22413
Molecular Weight:
104923.58 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
DENV-2
Pharmacological action
unknown
General Function:
Structural molecule activity
Specific Function:
Capsid protein C self-assembles to form an icosahedral capsid about 30 nm in diameter. The capsid encapsulates the genomic RNA.prM acts as a chaperone for envelope protein E during intracellular virion assembly by masking and inactivating envelope protein E fusion peptide. prM is matured in the last step of virion assembly, presumably to avoid catastrophic activation of the viral fusion peptide...
Gene Name:
Not Available
Uniprot ID:
P12823
Molecular Weight:
379216.195 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Poly(a) rna binding
Specific Function:
ATP dependent phosphorylation of adenosine and other related nucleoside analogs to monophosphate derivatives. Serves as a potential regulator of concentrations of extracellular adenosine and intracellular adenine nucleotides.
Gene Name:
ADK
Uniprot ID:
P55263
Molecular Weight:
40545.075 Da
References
  1. Wu JZ, Larson G, Walker H, Shim JH, Hong Z: Phosphorylation of ribavirin and viramidine by adenosine kinase and cytosolic 5'-nucleotidase II: Implications for ribavirin metabolism in erythrocytes. Antimicrob Agents Chemother. 2005 Jun;49(6):2164-71. [PubMed:15917509 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Nucleoside transmembrane transporter activity
Specific Function:
Mediates both influx and efflux of nucleosides across the membrane (equilibrative transporter). It is sensitive (ES) to low concentrations of the inhibitor nitrobenzylmercaptopurine riboside (NBMPR) and is sodium-independent. It has a higher affinity for adenosine. Inhibited by dipyridamole and dilazep (anticancer chemotherapeutics drugs).
Gene Name:
SLC29A1
Uniprot ID:
Q99808
Molecular Weight:
50218.805 Da
References
  1. Yamamoto T, Sugawara M, Kikukawa T, Miyauchi S, Yamaguchi M, Tero A, Takagi S, Nakagaki T: Kinetic study of anti-viral ribavirin uptake mediated by hCNT3 and hENT1 in Xenopus laevis oocytes. Biophys Chem. 2010 Mar;147(1-2):59-65. doi: 10.1016/j.bpc.2009.12.012. Epub 2010 Jan 6. [PubMed:20096989 ]
  2. Fukuchi Y, Furihata T, Hashizume M, Iikura M, Chiba K: Characterization of ribavirin uptake systems in human hepatocytes. J Hepatol. 2010 Apr;52(4):486-92. doi: 10.1016/j.jhep.2010.01.011. Epub 2010 Feb 4. [PubMed:20185188 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Pyrimidine- and adenine-specific:sodium symporter activity
Specific Function:
Sodium-dependent, pyrimidine- and purine-selective. Involved in the homeostasis of endogenous nucleosides. Exhibits the transport characteristics of the nucleoside transport system cib or N3 subtype (N3/cib) (with marked transport of both thymidine and inosine). Employs a 2:1 sodium/nucleoside ratio. Also able to transport gemcitabine, 3'-azido-3'-deoxythymidine (AZT), ribavirin and 3-deazaurid...
Gene Name:
SLC28A3
Uniprot ID:
Q9HAS3
Molecular Weight:
76929.61 Da
References
  1. Yamamoto T, Sugawara M, Kikukawa T, Miyauchi S, Yamaguchi M, Tero A, Takagi S, Nakagaki T: Kinetic study of anti-viral ribavirin uptake mediated by hCNT3 and hENT1 in Xenopus laevis oocytes. Biophys Chem. 2010 Mar;147(1-2):59-65. doi: 10.1016/j.bpc.2009.12.012. Epub 2010 Jan 6. [PubMed:20096989 ]
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Drug created on June 13, 2005 07:24 / Updated on January 16, 2017 03:57