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
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
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
Title | Date | PubMed |
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Inhibition of vaccinia virus growth by the nucleoside analogue 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide (virazole, ribavirin). | 1976 Aug |
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Synthesis of tetrazole ribonucleosides and their evaluation as antiviral agents. | 1976 Feb |
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Effect of cytosine, arabinoside, iododeoxyuridine, ethyldeoxyuridine, thiocyanatodeoxyuridine, and ribavirin on tail lesion formation in mice infected with vaccinia virus. | 1976 Mar |
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Selective inhibition of arthropod-borne and arenaviruses in vitro by 3'-fluoro-3'-deoxyadenosine. | 1992 Jun |
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Treatment of severe recurrent hepatitis C after liver transplantation with ribavirin plus interferon alpha. | 1999 Feb-Mar |
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[Effect of ribavirin on dynamics of hepatitis C viremia in interferon alpha-treated patiens with response or no response]. | 2000 Nov |
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Factors influencing ribavirin-induced hemolysis. | 2001 Jun |
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A rapid assay for evaluation of antiviral activity against coxsackie virus B3, influenza virus A, and herpes simplex virus type 1. | 2001 Jun |
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In vivo influenza virus-inhibitory effects of the cyclopentane neuraminidase inhibitor RJW-270201. | 2001 Mar |
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Cyclopentane neuraminidase inhibitors with potent in vitro anti-influenza virus activities. | 2001 Mar |
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In vitro evaluation of secoiridoid glucosides from the fruits of Ligustrum lucidum as antiviral agents. | 2001 Nov |
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A preliminary study of erythropoietin for anemia associated with ribavirin and interferon-alpha. | 2001 Sep |
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Chronic hepatitis C in HIV infection: feasibility and sustained efficacy of therapy with interferon alfa-2b and tribavirin. | 2001 Sep 28 |
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Effect of ribavirin on epididymal sperm count in rat. | 2002 Jan |
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Ribavirin-induced sperm shape abnormalities in Wistar rat. | 2002 Jan 15 |
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Intravenous ribavirin treatment for severe adenovirus disease in immunocompromised children. | 2002 Jul |
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Nephrotoxicity of interferon alfa-ribavirin therapy for chronic hepatitis C. | 2002 Jul |
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Identification of active antiviral compounds against a New York isolate of West Nile virus. | 2002 Jul |
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Evaluation of the antiviral activity against Junin virus of macrocyclic trichothecenes produced by the hypocrealean epibiont of Baccharis coridifolia. | 2002 Mar |
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Treatment of ribavirin/interferon-induced anemia with erythropoietin in patients with hepatitis C. | 2002 May |
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Characterization of wild-type and cidofovir-resistant strains of camelpox, cowpox, monkeypox, and vaccinia viruses. | 2002 May |
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Treatment of acute hepatitis C virus infection with interferon-alpha 2b and ribavirin: case report and review of the literature. | 2002 Oct 14 |
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Hemoglobinuria with ribavirin treatment. | 2003 Apr |
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Ribavirin reduces clinical signs and pathological changes of experimental autoimmune encephalomyelitis in Dark Agouti rats. | 2003 Apr 15 |
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[Is chronic hepatitis C treatment as efficient in the general population as in randomised trials?]. | 2003 Aug-Sep |
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Normal erythropoietin response in chronic hepatitis C patients with ribavirin-induced anaemia. | 2003 Feb |
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Posterior segment complications in patients with hepatitis C treated with interferon and ribavirin. | 2003 Feb |
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Adherence and mental side effects during hepatitis C treatment with interferon alfa and ribavirin in psychiatric risk groups. | 2003 Feb |
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Successful treatment of giant cell hepatitis with Rebetron (interferon/ribavirin). | 2003 Jan |
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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 |
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The effect of ribavirin and IMPDH inhibitors on hepatitis C virus subgenomic replicon RNA. | 2003 Jun 5 |
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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 |
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Rosacea fulminans associated with pegylated interferon alpha-2B and ribavirin therapy. | 2003 Oct |
Sample Use Guides
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
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.
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Classification Tree | Code System | Code | ||
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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
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EMA ASSESSMENT REPORTS |
RIBAVIRIN TEVA (AUTHORIZED: HEPATITIS C, CHRONIC)
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WHO-ATC |
J05AP01
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FDA ORPHAN DRUG |
57491
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EMA ASSESSMENT REPORTS |
RIBAVIRIN TEVA PHARMA B.V. (AUTHORIZED: HEPATITIS C, CHRONIC)
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LIVERTOX |
842
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WHO-VATC |
QJ05AB04
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EMA ASSESSMENT REPORTS |
COTRONAK (REFUSED: HEPATITIS C, CHRONIC)
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NDF-RT |
N0000175459
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EU-Orphan Drug |
EU/3/01/024
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WHO-ESSENTIAL MEDICINES LIST |
6.4.3
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NCI_THESAURUS |
C281
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EMA ASSESSMENT REPORTS |
REBETOL (AUTHORIZED: HEPATITIS C, CHRONIC)
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WHO-ATC |
J05AB04
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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
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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
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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
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FDA ORPHAN DRUG |
162402
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EMA ASSESSMENT REPORTS |
RIBAVIRIN MYLAN (AUTHORIZED: HEPATITIS C, CHRONIC)
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Code System | Code | Type | Description | ||
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C807
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PRIMARY | |||
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3543
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PRIMARY | |||
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CHEMBL1643
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PRIMARY | |||
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D012254
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PRIMARY | |||
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36791-04-5
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PRIMARY | |||
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SUB10297MIG
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PRIMARY | |||
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COPEGUS
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PRIMARY | APPROVED MARCH 2015 | ||
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M9593
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PRIMARY | Merck Index | ||
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36791-04-5
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PRIMARY | |||
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36791-04-5
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DB00811
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36791-04-5
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PRIMARY | |||
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6842
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PRIMARY | |||
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66510-90-5
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SUPERSEDED | |||
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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
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PRIMARY | RxNorm | ||
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RIBAVIRIN
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PRIMARY | |||
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37542
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PRIMARY |
ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
PRODRUG (METABOLITE ACTIVE)