RIBAVIRIN

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 Search

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

Targets

Primary Target	Pharmacology	Condition	Potency
Hepatitis C virus NS5B RNA-dependent RNA polymerase 14	Inhibitor 6502	Hepatitis C, Chronic
Inosine-5'-monophosphate dehydrogenase 1 4	Inhibitor 6502	Respiratory Syncytial Virus Infections

Conditions

Condition	Modality	Targets	Highest Phase	Product
Respiratory Syncytial Virus Infections 4	Primary	Inosine-5'-monophosphate dehydrogenase 1	Approved 7817	VIRAZOLE
Hepatitis C, Chronic 30	Primary	Hepatitis C virus NS5B RNA-dependent RNA polymerase Inosine-5'-monophosphate dehydrogenase 1	Approved 7817	COPEGUS
Hepatitis C virus infection (in HIV-infected) 1			Approved (off-label) 8

PubMed

Title	Date	PubMed
The in vitro study of influence of four novel platinum compounds on rodent melanoma cells.	2001 May-Jun	11712733

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

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