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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H12N4O5
Molecular Weight 244.2047
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIBAVIRIN

SMILES

NC(=O)C1=NN(C=N1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O

InChI

InChIKey=IWUCXVSUMQZMFG-AFCXAGJDSA-N
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

HIDE SMILES / InChI

Molecular Formula C8H12N4O5
Molecular Weight 244.2047
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Ribavirin is a synthetic nucleoside analogue, which was first discovered and developed in 1970 by researchers from the International Chemical & Nuclear Corporation (ICN), today known as Valeant Pharmaceuticals. Ribavirin was initially approved for use in humans to treat pediatric respiratory syncytial virus infections (RSV). In cell cultures the inhibitory activity of ribavirin for RSV is selective. The mechanism of action is unknown. Reversal of the in vitro antiviral activity by guanosine or xanthosine suggests ribavirin may act as an analogue of these cellular metabolites. There were no other significant advancements in the treatment of hepatitis C until 1998, when the combination of ribavirin and interferon-alpha gained approval. Clinically, ribavirin showed a small, additive antiviral effect in combination with interferon, but its main effect was dose-dependent prevention of virological relapse. The mechanism by which the combination of ribavirin and an interferon product exerts its effects against the hepatitis C virus has not been fully established. However, it could be thorough the inhibition of inosine monophosphate dehydrogenase (IMPDH), which is the key step in de novo guanine synthesis, a requirement for viral replication.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Efficacy of 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide against influenza virus infections in mice.
1975 May
Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives.
1992 Nov 27
Treatment of cowpox virus respiratory infections in mice with ribavirin as a single agent or followed sequentially by cidofovir.
2000 Jul
[Effect of ribavirin on dynamics of hepatitis C viremia in interferon alpha-treated patiens with response or no response].
2000 Nov
Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections.
2001 Apr
Ribavirin--current status of a broad spectrum antiviral agent.
2001 Aug
Synthesis, mechanism of action, and antiviral activity of a new series of covalent mechanism-based inhibitors of S-adenosyl-L-homocysteine hydrolase.
2001 Aug 16
Increased mitochondrial toxicity with ribavirin in HIV/HCV coinfection.
2001 Jan 27
Inhibition of measles virus replication by 5'-nor carbocyclic adenosine analogues.
2001 Jul
Factors influencing ribavirin-induced hemolysis.
2001 Jun
Cyclopentane neuraminidase inhibitors with potent in vitro anti-influenza virus activities.
2001 Mar
Antiviral activity and mode of action studies of ribavirin and mycophenolic acid against orthopoxviruses in vitro.
2001 Nov
In vitro evaluation of secoiridoid glucosides from the fruits of Ligustrum lucidum as antiviral agents.
2001 Nov
A preliminary study of erythropoietin for anemia associated with ribavirin and interferon-alpha.
2001 Sep
Chronic hepatitis C in HIV infection: feasibility and sustained efficacy of therapy with interferon alfa-2b and tribavirin.
2001 Sep 28
Management strategies for ribavirin-induced hemolytic anemia in the treatment of hepatitis C: clinical and economic implications.
2001 Sep-Oct
In vitro and in vivo activities of anti-influenza virus compound T-705.
2002 Apr
[Novel mode of action of ribavirin (Rebetol), a drug for the treatment of chronic hepatitis C: inducting the mutation of RNA viruses].
2002 Dec
Sustained suppression of hepatitis C virus by interferon and ribavirin in hemophilic patients not responding to interferon monotherapy.
2002 Feb 1
Antiviral activity of brassinosteroids derivatives against measles virus in cell cultures.
2002 Jan
Nephrotoxicity of interferon alfa-ribavirin therapy for chronic hepatitis C.
2002 Jul
Cidofovir in the treatment of poxvirus infections.
2002 Jul
New 2-(1-adamantylcarbonyl)pyridine and 1-acetyladamantane thiosemicarbazones-thiocarbonohydrazones: cell growth inhibitory, antiviral and antimicrobial activity evaluation.
2002 Mar 11
Mechanism of action of ribavirin in the combination treatment of chronic HCV infection.
2002 May
Inhibition of the replication of a hepatitis C virus-like RNA template by interferon and 3'-deoxycytidine.
2002 Nov
Inhibitors of the IMPDH enzyme as potential anti-bovine viral diarrhoea virus agents.
2002 Nov
The quest for an efficacious antiviral for respiratory syncytial virus.
2002 Nov
Search of antimicrobial activity of selected non-antibiotic drugs.
2002 Nov-Dec
Premature discontinuation of interferon plus ribavirin for adverse effects: a multicentre survey in 'real world' patients with chronic hepatitis C.
2002 Sep
Meta-analysis: ribavirin-induced haemolytic anaemia in patients with chronic hepatitis C.
2002 Sep
Anemia in the treatment of hepatitis C virus infection.
2003
Peginterferon-alpha-2a (40kD) plus ribavirin: a review of its use in the management of chronic hepatitis C.
2003
Ribavirin reduces clinical signs and pathological changes of experimental autoimmune encephalomyelitis in Dark Agouti rats.
2003 Apr 15
Interferon and ribavirin treatment in patients with hepatitis C-associated renal disease and renal insufficiency.
2003 Aug
Combination therapy in the treatment of chronic viral hepatitis and prevention of hepatocellular carcinoma.
2003 Aug
Synthesis of 1,2,3-triazolo-carbanucleoside analogues of ribavirin targeting an HCV in replicon.
2003 Aug 15
[Is chronic hepatitis C treatment as efficient in the general population as in randomised trials?].
2003 Aug-Sep
Normal erythropoietin response in chronic hepatitis C patients with ribavirin-induced anaemia.
2003 Feb
In vitro activity of potential anti-poxvirus agents.
2003 Jan
Successful treatment of giant cell hepatitis with Rebetron (interferon/ribavirin).
2003 Jan
Synergistic in vitro interactions between alpha interferon and ribavirin against bovine viral diarrhea virus and yellow fever virus as surrogate models of hepatitis C virus replication.
2003 Jul
Correlation of sICAM-1 and sVCAM-1 level with biochemical, histological and viral findings in chronic hepatitis C after interferon-alpha + ribavirin therapy.
2003 Jun
Severe migraine headaches are caused by ribavirin but not by interferon alpha-2B in combination therapy for chronic hepatitis C.
2003 Jun
A pilot study of eicosapentaenoic acid therapy for ribavirin-related anemia in patients with chronic hepatitis C.
2003 Jun
The effect of ribavirin and IMPDH inhibitors on hepatitis C virus subgenomic replicon RNA.
2003 Jun 5
Interferon, ribavirin, 6-azauridine and glycyrrhizin: antiviral compounds active against pathogenic flaviviruses.
2003 Mar
Two distinct phases of virus-induced nuclear factor kappa B regulation enhance tumor necrosis factor-related apoptosis-inducing ligand-mediated apoptosis in virus-infected cells.
2003 May 16
How can we identify better those with recurrent hepatitis C who will respond to therapy? What are the optimal treatment regimen and treatment duration?
2003 Nov
[Use of erythropoietin in the treatment of anemia induced by ribavirin/interferon in patients with hepatitis C].
2003 Oct
Treatment of interferon-induced psychosis in patients with comorbid hepatitis C and HIV.
2003 Sep-Oct
Patents

Sample Use Guides

In Vivo Use Guide
respiratory syncytial virus infection: 20 mg/mL VIRAZOLE (Ribavirin for inhalation solution) as the starting solution in the drug reservoir of the SPAG-2 unit, with continuous aerosol administration for 12-18 hours per day for 3 to 7 days. Using the recommended drug concentration of 20 mg/mL the average aerosol concentration for a 12 hour delivery period would be 190 micrograms/liter of air. Aerosolized VIRAZOLE should not be administered in a mixture for combined aerosolization or simultaneously with other aerosolized medications. Chronic hepatitis C virus infection: The recommended duration of treatment for patients previously untreated with ribavirin and interferon is 24 to 48 weeks. The daily dose of COPEGUS (ribavirin) tablets is 800 mg to 1200 mg administered orally in two divided doses. The dose should be individualized to the patient depending on baseline disease characteristics (eg, genotype), response to therapy, and tolerability of the regimen.
Route of Administration: oral; respiratory
In Vitro Use Guide
To determine the optimal concentration and timing of ribavirin treatment for the inhibition of viral transcription, Human A549 pulmonary type II epithelial cells pretreated (2 h) or posttreated (1 h) with increasing concentrations of ribavirin (from10 to 100 microg/ml) were exposed to pRSV (Respiratory syncytial virus). Total cellular RNA was harvested 36 h later, and the abundance of the 1.1-kb RSV N transcript was measured by Northern blotting. Ribavirin treatment potently inhibited RSV transcription, thereby reducing the level of RSV N transcripts to approximately 13% of levels in nontreated cells. In RSV-infected epithelial cells, ribavirin reduces plaque formation, the release of infectious virions, and F glycoprotein expression.
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:47:30 UTC 2019
Edited
by admin
on Mon Oct 21 20:47:30 UTC 2019
Record UNII
49717AWG6K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RIBAVIRIN
EMA EPAR   EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
COPEGUS
Brand Name English
COTRONAK
Brand Name English
RBV
Common Name English
RIBAVIRIN [INN]
Common Name English
1H-1,2,4-TRIAZOLE-3-CARBOXAMIDE, 1-.BETA.-D-RIBOFURANOSYL-
Common Name English
RIBAVIRIN [HSDB]
Common Name English
RIBAVIRIN [EMA EPAR]
Common Name English
SCH 18908
Code English
SCH-18908
Code English
NSC-163039
Code English
RIBAVIRIN BIOPARTNERS
Brand Name English
RIBAVIRIN [MI]
Common Name English
RIBAVIRIN TEVA PHARMA B.V.
Brand Name English
REBETOL
Brand Name English
RIBAVIRIN MYLAN
Brand Name English
RIBAVIRIN [VANDF]
Common Name English
RIBAVIRIN [JAN]
Common Name English
RIBAVIRIN [MART.]
Common Name English
RIBAVIRIN [USP]
Common Name English
RIBAVIRIN [ORANGE BOOK]
Common Name English
RIBAVIRIN COMPONENT OF PEGINTERFERON
Common Name English
VIRAZOLE
Brand Name English
RIBASPHERE
Brand Name English
RIBAVIRIN [WHO-DD]
Common Name English
RIBAVIRIN [USAN]
Common Name English
RIBAVIRIN [EP]
Common Name English
RIBAVIRIN TEVA
Brand Name English
1-.BETA.-D-RIBOFURANOSYL-1H-1,2,4-TRIAZOLE-3-CARBOXAMIDE
Common Name English
RIBAVIRIN [USP-RS]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175466
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
EMA ASSESSMENT REPORTS RIBAVIRIN TEVA (AUTHORIZED: HEPATITIS C, CHRONIC)
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
WHO-ATC J05AP01
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
FDA ORPHAN DRUG 57491
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
EMA ASSESSMENT REPORTS RIBAVIRIN TEVA PHARMA B.V. (AUTHORIZED: HEPATITIS C, CHRONIC)
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
LIVERTOX 842
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
WHO-VATC QJ05AB04
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
EMA ASSESSMENT REPORTS COTRONAK (REFUSED: HEPATITIS C, CHRONIC)
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
NDF-RT N0000175459
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
EU-Orphan Drug EU/3/01/024
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.4.3
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
NCI_THESAURUS C281
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
EMA ASSESSMENT REPORTS REBETOL (AUTHORIZED: HEPATITIS C, CHRONIC)
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
WHO-ATC J05AB04
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
NDF-RT N0000175459
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
NDF-RT N0000175459
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
EMA ASSESSMENT REPORTS RIBAVIRIN BIOPARTNERS (WITHDRAWN: HEPATITIS C, CHRONIC)
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
FDA ORPHAN DRUG 162402
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
EMA ASSESSMENT REPORTS RIBAVIRIN MYLAN (AUTHORIZED: HEPATITIS C, CHRONIC)
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
Code System Code Type Description
NCI_THESAURUS
C807
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
PRIMARY
INN
3543
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
PRIMARY
ChEMBL
CHEMBL1643
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
PRIMARY
MESH
D012254
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
PRIMARY
CAS
36791-04-5
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
PRIMARY
EVMPD
SUB10297MIG
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
PRIMARY
JAPANESE REVIEW
COPEGUS
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
PRIMARY APPROVED MARCH 2015
MERCK INDEX
M9593
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
PRIMARY Merck Index
EPA CompTox
36791-04-5
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
PRIMARY
LactMed
36791-04-5
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
PRIMARY
DRUG BANK
DB00811
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
PRIMARY
HSDB
36791-04-5
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
PRIMARY
IUPHAR
6842
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
PRIMARY
CAS
66510-90-5
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
SUPERSEDED
RXCUI
9344
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
PRIMARY RxNorm
WIKIPEDIA
RIBAVIRIN
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
PRIMARY
PUBCHEM
37542
Created by admin on Mon Oct 21 20:47:30 UTC 2019 , Edited by admin on Mon Oct 21 20:47:30 UTC 2019
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
Related Record Type Details
METABOLITE -> PARENT
a degradative pathway involving deribosylation and amide hydrolysis to yield a triazole carboxylic acid metabolite; Excreted renally
METABOLITE -> PARENT
BY adenosine kinase
METABOLITE -> PARENT
a degradative pathway involving deribosylation and amide hydrolysis to yield a triazole carboxylic acid metabolite; excreted renally.
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 2.3
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
Related Record Type Details
ACTIVE MOIETY