U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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
Inhibition of vaccinia virus growth by the nucleoside analogue 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide (virazole, ribavirin).
1976 Aug
Synthesis of tetrazole ribonucleosides and their evaluation as antiviral agents.
1976 Feb
Effect of cytosine, arabinoside, iododeoxyuridine, ethyldeoxyuridine, thiocyanatodeoxyuridine, and ribavirin on tail lesion formation in mice infected with vaccinia virus.
1976 Mar
Antiviral and antitumor structure-activity relationship studies on tetracyclic eudistomines.
1992 Aug 21
Selective inhibition of arthropod-borne and arenaviruses in vitro by 3'-fluoro-3'-deoxyadenosine.
1992 Jun
(+-)-carbocyclic 5'-nor-2'-deoxyguanosine and related purine derivatives: synthesis and antiviral properties.
1992 Jun 12
Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives.
1992 Nov 27
Broad-spectrum antiviral activity of the IMP dehydrogenase inhibitor VX-497: a comparison with ribavirin and demonstration of antiviral additivity with alpha interferon.
2000 Apr
Antiviral activity of mixed-valence rare earth borotungstate heteropoly blues against influenza virus in mice.
2000 Nov
Respiratory tract infections caused by respiratory syncytial virus in children. Diagnosis and treatment.
2001 Apr
Uric acid nephrolithiasis associated with interferon and ribavirin treatment of hepatitis C.
2001 Apr
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
A rapid assay for evaluation of antiviral activity against coxsackie virus B3, influenza virus A, and herpes simplex virus type 1.
2001 Jun
In vivo influenza virus-inhibitory effects of the cyclopentane neuraminidase inhibitor RJW-270201.
2001 Mar
The in vitro study of influence of four novel platinum compounds on rodent melanoma cells.
2001 May-Jun
Antiviral activity and mode of action studies of ribavirin and mycophenolic acid against orthopoxviruses in vitro.
2001 Nov
Novel carbocyclic nucleosides containing a cyclobutyl ring: adenosine analogues.
2001 Sep
Management strategies for ribavirin-induced hemolytic anemia in the treatment of hepatitis C: clinical and economic implications.
2001 Sep-Oct
[ROC curve analysis of factors predictive of response to treatment with interferon plus ribavirin in patients with chronic hepatitis C relapse after previous interferon treatment].
2002 Dec
[Novel mode of action of ribavirin (Rebetol), a drug for the treatment of chronic hepatitis C: inducting the mutation of RNA viruses].
2002 Dec
Effect of ribavirin on epididymal sperm count in rat.
2002 Jan
Ribavirin-induced sperm shape abnormalities in Wistar rat.
2002 Jan 15
Intravenous ribavirin treatment for severe adenovirus disease in immunocompromised children.
2002 Jul
Nephrotoxicity of interferon alfa-ribavirin therapy for chronic hepatitis C.
2002 Jul
Identification of active antiviral compounds against a New York isolate of West Nile virus.
2002 Jul
Cidofovir in the treatment of poxvirus infections.
2002 Jul
1-beta-D-arabinofuranosylcytosine inhibits borna disease virus replication and spread.
2002 Jun
Interferon-alpha induced transient thyroid dysfunction in hepatitis C.
2002 Mar
Combination treatment of influenza A virus infections in cell culture and in mice with the cyclopentane neuraminidase inhibitor RWJ-270201 and ribavirin.
2002 May
Treatment of ribavirin/interferon-induced anemia with erythropoietin in patients with hepatitis C.
2002 May
Mechanism of action of ribavirin in the combination treatment of chronic HCV infection.
2002 May
Heterocyclic nucleoside analogues: design and synthesis of antiviral, modified nucleosides containing isoxazole heterocycles.
2002 May 20
Comparison of colorimetric, fluorometric, and visual methods for determining anti-influenza (H1N1 and H3N2) virus activities and toxicities of compounds.
2002 Oct
Treatment of acute hepatitis C virus infection with interferon-alpha 2b and ribavirin: case report and review of the literature.
2002 Oct 14
U.S. veterans' experience with rebetron in a nonstudy environment: success or failure?
2002 Sep
Anemia in the treatment of hepatitis C virus infection.
2003
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
Posterior segment complications in patients with hepatitis C treated with interferon and ribavirin.
2003 Feb
Adherence and mental side effects during hepatitis C treatment with interferon alfa and ribavirin in psychiatric risk groups.
2003 Feb
In vitro activity of potential anti-poxvirus agents.
2003 Jan
Potential antiviral therapeutics for smallpox, monkeypox and other orthopoxvirus infections.
2003 Jan
[52-year-old patient with subcutaneous space-occupying lesion in immunosuppression].
2003 Jun
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
Rosacea fulminans associated with pegylated interferon alpha-2B and ribavirin therapy.
2003 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.
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