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

Molecular Formula	C8H12N4O5
Molecular Weight	244.2047
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/21511_Copegus_lbl.pdf
Curator's Comment: description was created based on several sources, including https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=adf16e64-345f-469a-b987-3fbdd17e0ac2 | http://www.news-medical.net/health/Ribavirin-History.aspx

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
Inosine-5'-monophosphate dehydrogenase 1 4 Target ID: CHEMBL1822 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16293677	Inhibitor 8504
Hepatitis C virus NS5B RNA-dependent RNA polymerase 14 Target ID: CHEMBL5375 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16107837	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Respiratory syncytial virus infection 4 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=adf16e64-345f-469a-b987-3fbdd17e0ac2	Primary		Approved 8583	VIRAZOLE Approved Use VIRAZOLE (Ribavirin for Inhalation Solution, USP) is indicated for the treatment of hospitalized infants and young children with severe lower respiratory tract infections due to respiratory syncytial virus. Treatment early in the course of severe lower respiratory tract infection may be necessary to achieve efficacy. Only severe RSV lower respiratory tract infection should be treated with VIRAZOLE. The vast majority of infants and children with RSV infection have disease that is mild, self-limited, and does not require hospitalization or antiviral treatment. Many children with mild lower respiratory tract involvement will require shorter hospitalization than would be required for a full course of VIRAZOLE aerosol (3 to 7 days) and should not be treated with the drug. Thus the decision to treat with VIRAZOLE should be based on the severity of the RSV infection. The presence of an underlying condition such as prematurity, immunosuppression or cardiopulmonary disease may increase the severity of clinical manifestations and complications of RSV infection. Use of aerosolized VIRAZOLE in patients requiring mechanical ventilator assistance should be undertaken only by physicians and support staff familiar with this mode of administration and the specific ventilator being used Launch Date 1985
Chronic hepatitis C 42 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/21511_Copegus_lbl.pdf	Primary		Approved 8583	COPEGUS Approved Use COPEGUS in combination with PEGASYS (peginterferon alfa-2a) is indicated for the treatment of adults with chronic hepatitis C virus infection who have compensated liver disease and have not been previously treated with interferon alpha. Patients in whom efficacy was demonstrated included patients with compensated liver disease and histological evidence of cirrhosis (Child-Pugh class A). Launch Date 2002

C_max

Value	Dose	Co-administered	Analyte	Population
3680 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020903s052,021546s008lbl.pdf	600 mg 2 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		RIBAVIRIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
228000 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020903s052,021546s008lbl.pdf	600 mg 2 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		RIBAVIRIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
298 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020903s052,021546s008lbl.pdf	600 mg 2 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		RIBAVIRIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
600 mg 1 times / day multiple, oral Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33617629	unhealthy, 21 years Health Status: unhealthy Age Group: 21 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/33617629	Disc. AE: Hyperuricemia, Injury to kidney... AEs leading to discontinuation/dose reduction: Hyperuricemia (severe, 1 patient) Injury to kidney (acute, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/33617629
2400 mg 1 times / day multiple, oral Highest studied dose Dose: 2400 mg, 1 times / day Route: oral Route: multiple Dose: 2400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2444379	unhealthy, 39.9 years (range: 27 - 51 years) Health Status: unhealthy Age Group: 39.9 years (range: 27 - 51 years) Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/2444379	Disc. AE: Nausea, Vomiting... Other AEs: CNS disorder (NOS), Fatigue... AEs leading to discontinuation/dose reduction: Nausea (1 patient) Vomiting (1 patient) Headache (severe, 1 patient) Hematocrit low (1 patient) Other AEs: CNS disorder (NOS) (severe, 3 patients) Fatigue (3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/2444379
16 mg/kg 4 times / day multiple, intravenous Highest studied dose Dose: 16 mg/kg, 4 times / day Route: intravenous Route: multiple Dose: 16 mg/kg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/21544005	unhealthy, 6-10 years Health Status: unhealthy Age Group: 6-10 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/21544005	Disc. AE: Nonprotein nitrogen blood increased, Abdominal pain... AEs leading to discontinuation/dose reduction: Nonprotein nitrogen blood increased (1 patient) Abdominal pain (1 patient) Tenderness (1 patient) Anorexia (1 patient) Pancreatic enzymes increased (1 patient) Pancreatitis (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/21544005
1200 mg 1 times / day multiple, oral Recommended Dose: 1200 mg, 1 times / day Route: oral Route: multiple Dose: 1200 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/21511_Copegus_lbl.pdf	pregnant Health Status: pregnant Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/21511_Copegus_lbl.pdf	Other AEs: Fetal death... Other AEs: Fetal death (grade 5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/21511_Copegus_lbl.pdf
1200 mg 1 times / day multiple, oral Recommended Dose: 1200 mg, 1 times / day Route: oral Route: multiple Dose: 1200 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/21511_Copegus_lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/21511_Copegus_lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/21511_Copegus_lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	substrate 1193 inhibitor 2438	substrate 1388 inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2C19 2057 CYP2E1 1060	CYP1A2 1197 CYP2A6 626 CYP2C19 1119 CYP2E1 729

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20903_INTRON%20A%20REBETOL_BIOPHARMR.PDF#page=16 Page: 16.0	no
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20903_INTRON%20A%20REBETOL_BIOPHARMR.PDF#page=16 Page: 16.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20903_INTRON%20A%20REBETOL_BIOPHARMR.PDF#page=16 Page: 16.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20903_INTRON%20A%20REBETOL_BIOPHARMR.PDF#page=16 Page: 16.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20903_INTRON%20A%20REBETOL_BIOPHARMR.PDF#page=16 Page: 16.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20903_INTRON%20A%20REBETOL_BIOPHARMR.PDF#page=16 Page: 16.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20903_INTRON%20A%20REBETOL_BIOPHARMR.PDF#page=16 Page: 16.0	no

Drug as victim

Target	Modality	Activity
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20903_INTRON%20A%20REBETOL_BIOPHARMR.PDF#page=16 Page: 16.0	no
CYP2A6 626	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20903_INTRON%20A%20REBETOL_BIOPHARMR.PDF#page=16 Page: 16.0	no
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20903_INTRON%20A%20REBETOL_BIOPHARMR.PDF#page=16 Page: 16.0	no
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20903_INTRON%20A%20REBETOL_BIOPHARMR.PDF#page=16 Page: 16.0	no
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20903_INTRON%20A%20REBETOL_BIOPHARMR.PDF#page=16 Page: 16.0	no
CYP2E1 729	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20903_INTRON%20A%20REBETOL_BIOPHARMR.PDF#page=16 Page: 16.0	no
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20903_INTRON%20A%20REBETOL_BIOPHARMR.PDF#page=16 Page: 16.0	no

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:63580	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63580
ChemicalBook	CB0689324	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0689324
eMolecules	1944721	https://www.emolecules.com/cgi-bin/more?vid=1944721
MolPort	MolPort-002-507-104	https://www.molport.com/shop/molecule-link/MolPort-002-507-104
Selleck Chemicals	Ribavirin(Copegus)	http://www.selleckchem.com/products/Ribavirin(Copegus).html
ZINC	ZINC000001035331	http://zinc15.docking.org/substances/ZINC000001035331

PubMed

Title	Date	PubMed
How can we identify better those with recurrent hepatitis C who will respond to therapy? What are the optimal treatment regimen and treatment duration?	2003-11	14586905
[Is chronic hepatitis C treatment as efficient in the general population as in randomised trials?].	2003-10-31	14586246
[Use of erythropoietin in the treatment of anemia induced by ribavirin/interferon in patients with hepatitis C].	2003-10	14568602
Rosacea fulminans associated with pegylated interferon alpha-2B and ribavirin therapy.	2003-10	14558405
Treatment of interferon-induced psychosis in patients with comorbid hepatitis C and HIV.	2003-09-05	12954918
Intracerebral haemorrhage and hepatitis C treatment.	2003-09	12969193
Synthesis of 1,2,3-triazolo-carbanucleoside analogues of ribavirin targeting an HCV in replicon.	2003-08-15	12901908
Interferon and ribavirin treatment in patients with hepatitis C-associated renal disease and renal insufficiency.	2003-08	12897097
Combination therapy in the treatment of chronic viral hepatitis and prevention of hepatocellular carcinoma.	2003-08	12860172
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.	2003-07	12821481
The effect of ribavirin and IMPDH inhibitors on hepatitis C virus subgenomic replicon RNA.	2003-06-05	12781720
[52-year-old patient with subcutaneous space-occupying lesion in immunosuppression].	2003-06	14567110
Correlation of sICAM-1 and sVCAM-1 level with biochemical, histological and viral findings in chronic hepatitis C after interferon-alpha + ribavirin therapy.	2003-06	12853993
Severe migraine headaches are caused by ribavirin but not by interferon alpha-2B in combination therapy for chronic hepatitis C.	2003-06	12763386
Ribavirin and alpha interferon enhance death receptor-mediated apoptosis and caspase activation in human hepatoma cells.	2003-06	12760867
A pilot study of eicosapentaenoic acid therapy for ribavirin-related anemia in patients with chronic hepatitis C.	2003-06	12736713
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.	2003-05-16	12637521
Ribavirin reduces clinical signs and pathological changes of experimental autoimmune encephalomyelitis in Dark Agouti rats.	2003-04-15	12672002
Search of antimicrobial activity of selected non-antibiotic drugs.	2003-04-03	12669766
Hemoglobinuria with ribavirin treatment.	2003-04	12642748
Interferon, ribavirin, 6-azauridine and glycyrrhizin: antiviral compounds active against pathogenic flaviviruses.	2003-03	12719009
Normal erythropoietin response in chronic hepatitis C patients with ribavirin-induced anaemia.	2003-02	12713065
Posterior segment complications in patients with hepatitis C treated with interferon and ribavirin.	2003-02	12578794
Adherence and mental side effects during hepatitis C treatment with interferon alfa and ribavirin in psychiatric risk groups.	2003-02	12540795
In vitro activity of potential anti-poxvirus agents.	2003-01	12615301
Potential antiviral therapeutics for smallpox, monkeypox and other orthopoxvirus infections.	2003-01	12615299
Successful treatment of giant cell hepatitis with Rebetron (interferon/ribavirin).	2003-01	12526974
Anemia in the treatment of hepatitis C virus infection.	2003	14582000
Peginterferon-alpha-2a (40kD) plus ribavirin: a review of its use in the management of chronic hepatitis C.	2003	12656650
[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].	2002-12	12587043
[Novel mode of action of ribavirin (Rebetol), a drug for the treatment of chronic hepatitis C: inducting the mutation of RNA viruses].	2002-12	12528471
Inhibition of the replication of a hepatitis C virus-like RNA template by interferon and 3'-deoxycytidine.	2002-11	12718408
Inhibitors of the IMPDH enzyme as potential anti-bovine viral diarrhoea virus agents.	2002-11	12718406
The quest for an efficacious antiviral for respiratory syncytial virus.	2002-11	12718405
Treatment of acute hepatitis C virus infection with interferon-alpha 2b and ribavirin: case report and review of the literature.	2002-10-14	12437778
Comparison of colorimetric, fluorometric, and visual methods for determining anti-influenza (H1N1 and H3N2) virus activities and toxicities of compounds.	2002-10	12367731
Emotional distress during interferon-alpha-2B and ribavirin treatment of chronic hepatitis C.	2002-09-26	12297606
U.S. veterans' experience with rebetron in a nonstudy environment: success or failure?	2002-09	12358260
Premature discontinuation of interferon plus ribavirin for adverse effects: a multicentre survey in 'real world' patients with chronic hepatitis C.	2002-09	12197842
Meta-analysis: ribavirin-induced haemolytic anaemia in patients with chronic hepatitis C.	2002-09	12197841
Synthesis and antiviral evaluation of a mutagenic and non-hydrogen bonding ribonucleoside analogue: 1-beta-D-Ribofuranosyl-3-nitropyrrole.	2002-07-23	12119016
Intravenous ribavirin treatment for severe adenovirus disease in immunocompromised children.	2002-07	12093990
Interferon-alpha induced transient thyroid dysfunction in hepatitis C.	2002-03	12185880
Antiviral activity of brassinosteroids derivatives against measles virus in cell cultures.	2002-01	12180649
Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives.	1992-11-27	1335077
Antiviral and antitumor structure-activity relationship studies on tetracyclic eudistomines.	1992-08-21	1324318
(+-)-carbocyclic 5'-nor-2'-deoxyguanosine and related purine derivatives: synthesis and antiviral properties.	1992-06-12	1319491
Selective inhibition of arthropod-borne and arenaviruses in vitro by 3'-fluoro-3'-deoxyadenosine.	1992-06	1365816
Effect of cytosine, arabinoside, iododeoxyuridine, ethyldeoxyuridine, thiocyanatodeoxyuridine, and ribavirin on tail lesion formation in mice infected with vaccinia virus.	1976-03	1257248
Synthesis of tetrazole ribonucleosides and their evaluation as antiviral agents.	1976-02	1249809

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: Other

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 Mar 31 18:01:58 GMT 2025` Edited by `admin` on `Mon Mar 31 18:01:58 GMT 2025`
Record UNII	49717AWG6K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

COPEGUS

Preferred Name

English

RIBAVIRIN

Official Name

English

COTRONAK

Brand Name

English

RIBAVIRIN [USP MONOGRAPH]

Common 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

Ribavirin [WHO-DD]

Common Name

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 [EP MONOGRAPH]

Common Name

English

RIBAVIRIN [VANDF]

Common Name

English

RIBAVIRIN [JAN]

Common Name

English

RIBAVIRIN [MART.]

Common Name

English

RIBAVIRIN [ORANGE BOOK]

Common Name

English

VIRAZOLE

Brand Name

English

RIBASPHERE

Brand Name

English

RIBAVIRIN [USAN]

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