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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
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
Cidofovir in the treatment of poxvirus infections.
2002 Jul
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
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
[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
Intracerebral haemorrhage and hepatitis C treatment.
2003 Sep
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 Tue Mar 06 10:58:42 UTC 2018
Edited
by admin
on Tue Mar 06 10:58:42 UTC 2018
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 Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
EMA ASSESSMENT REPORTS RIBAVIRIN TEVA (AUTHORIZED: HEPATITIS C, CHRONIC)
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
EMA ASSESSMENT REPORTS RIBAVIRIN TEVA PHARMA B.V. (AUTHORIZED: HEPATITIS C, CHRONIC)
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
LIVERTOX 842
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
WHO-VATC QJ05AB04
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
EMA ASSESSMENT REPORTS COTRONAK (REFUSED: HEPATITIS C, CHRONIC)
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
NDF-RT N0000175459
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
WHO-ESSENTIAL MEDICINES LIST 6.4.3
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
EMA ASSESSMENT REPORTS REBETOL (AUTHORIZED: HEPATITIS C, CHRONIC)
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
WHO-ATC J05AB04
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
NDF-RT N0000175459
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
NDF-RT N0000175459
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
EMA ASSESSMENT REPORTS RIBAVIRIN BIOPARTNERS (WITHDRAWN: HEPATITIS C, CHRONIC)
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
EMA ASSESSMENT REPORTS RIBAVIRIN MYLAN (AUTHORIZED: HEPATITIS C, CHRONIC)
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
Code System Code Type Description
NCI_THESAURUS
C807
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
PRIMARY
INN
3543
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
PRIMARY
ChEMBL
CHEMBL1643
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
PRIMARY
MESH
D012254
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
PRIMARY
CAS
36791-04-5
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
PRIMARY
EVMPD
SUB10297MIG
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
PRIMARY
JAPANESE REVIEW
COPEGUS
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
PRIMARY APPROVED MARCH 2015
MERCK INDEX
M9593
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
PRIMARY Merck Index
EPA CompTox
36791-04-5
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
PRIMARY
LactMed
36791-04-5
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
PRIMARY
DRUG BANK
DB00811
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
PRIMARY
HSDB
36791-04-5
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
PRIMARY
IUPHAR
6842
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
PRIMARY
RXCUI
9344
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
PRIMARY RxNorm
WIKIPEDIA
RIBAVIRIN
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
PRIMARY
PUBCHEM
37542
Created by admin on Tue Mar 06 10:58:42 UTC 2018 , Edited by admin on Tue Mar 06 10:58:42 UTC 2018
PRIMARY SWITZERF
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