NAV

Ribavirin

Identification

Summary

Ribavirinis a guanosine nucleoside used to treat some forms of Hepatitis C.

Brand Names
Ibavyr, Rebetol, Virazole
Generic Name
Ribavirin
DrugBank Accession Number
DB00811
Background

Producing a broad-spectrum activity against several RNA and DNA viruses, Ribavirin is a synthetic guanosine nucleoside and antiviral agent that interferes with the synthesis of viral mRNA. It is primarily indicated for use in treating hepatitis C and viral hemorrhagic fevers. HCV is a single-stranded RNA virus that is categorized into nine distinct genotypes, with genotype 1 being the most common in the United States, and affecting 72% of all chronic HCV patients9. It is reported that ribavirin might be only effective in early stages of viral hemorrhagic fevers including Lasser fever, Crimean-Congo hemorrhagic fever, Venezuelan hemorrhagic fever, and Hantavirus infection. Ribavirin is a prodrug that is metabolized into nucleoside analogs that blocks viral RNA synthesis and viral mRNA capping. Before the development of newer drugs, ribavirin andPeginterferon alfa-2a/Peginterferon alfa-2bdual therapy was considered the first-generation and standard antiviral treatment5. The dual therapy was administered for 48 weeks in patients with genotype 1, 4, 5, and 6, and 24 weeks in patients with genotype 2 and 35. Newer drugs developed as Hepatitis C viral infection treatments can be used to reduce or eliminate the use of ribavirin, which are associated with serious adverse effects. They also improve therapeutic efficacy in patients with failedPeginterferon alfa-2a/Peginterferon alfa-2band ribavirin-based therapy. The potential use of ribavirin as a treatment for acute myeloid leukemia is currently under investigation.

According to 2017 American Association for the Study of Liver Diseases (AASLD) and 2015 consensus guidelines from the Canadian Association for the Study of the Liver (CASL), ribavirin is typically used as an adjunct therapy to various first-line and second-line combination therapies recommended for each genotypes. Ribavirin is added to decrease relapse rates by accelerating viral clearance early in the treatment course7. When used to treat Hepatitis C virus (HCV) infections, it is always used as a part of combination therapies as ribavirin monotherapy is not efficacious in the treatment of chronic hepatitis C infection6. Additionally, including ribavirin in the regimen can increase the risk of anemia.

In HCV genotye 1/2/3/4/5/6 patients, ribavirin can be used in combination therapy involvingDaclatasvirandSofosbuvir, Eplusa (Sofosbuvir,Velpatasvir), Harvoni (Sofosbuvir,Ledipasvir),SimeprevirandSofosbuvir, Viekira Pak (Ombitasvir,Paritaprevir,Ritonavir,Dasabuvir), Technivie (Ritonavir,Ombitasvir,Paritaprevir) and Zepatier (Elbasvir,Grazoprevir). Addition of weight-based ribavirin to Technivie therapy increased sustained virologic response after 12 weeks of daily therapy (SVR12) from 90% to 97% in patients with HCV genotype 1a and 90.9% to 100% in HCV genotype 4 patients9. Zepatier therapy along with ribavirin improved SVR in HCV genotype 5 patients. Combination therapy of ribavirin andPeginterferon alfa-2aresults in the SVR of 44% in patients with genotype 1 infection and 70% in patients with genotype 2-6. The inclusion of ribavirin in the combination therapies depend on individual patient's profile, for example if HCV genotype 3 patient has a Y93H genetic variant and compensated cirrhosis.

Type
Small Molecule
Groups
Approved
Structure
 3D
Similar Structures
Weight
Average: 244.2047
Monoisotopic: 244.080769514
Chemical Formula
C8H12N4O5
Synonyms
  • 1-beta-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide
  • 1-beta-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide
  • RBV
  • Ribavirin
  • Ribavirina
  • Ribavirine
  • Ribavirinum
  • Tribavirin
External IDs
  • ICN 1229
  • SCH 18908
  • SCH-18908

Pharmacology

Indication

Indicated for the treatment of chronic Hepatitis C virus (HCV) infection in combination with other antiviral agents with the intent to cure or achieve a sustained virologic response (SVR). Typically added to improve SVR and reduce relapse rates6.

The addition of ribavirin in Technivie therapy indicated for treating HCV genotype 1a and 4 infections is recommended in patients with or without cirrhosis.

Resistance: viral genetic determinants resulting in variable response to ribavirin therapy has not been yet determined.

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Ribavirin mediates direct antiviral activity against a number of DNA and RNA viruses by increasing the mutation frequency in the genomes of several RNA viruses. It is a member of the nucleoside antimetabolite drugs that interfere with duplication of the viral genetic material. The drug inhibits the activity of the enzyme RNA dependent RNA polymerase, due to its resemblence to building blocks of the RNA molecules.

Mechanism of action

Ribavirin is reported to have several mechanism of actions that lead to inhibition of viral RNA and protein synthesis. After activation by adenosine kinase to ribavirin mono-, di-, and triphosphate metabolites. Ribavirin triphosphate (RTP) is the predominant metabolite which directly inhibits viral mRNA polymerase by binding to the nucleotide binding site of the enzyme. This prevents the binding of the correct nucleotides, leading to a reduction in viral replication or to the production of defective virions7. RTP also demonstrates an inhibitory action on viral mRNA guanylyltransferase and mRNA 2′-O-methyltransferase of dengue virus. Inhibition of these enzymes disrupts the posttranslational capping of the 5′ end of viral mRNA through ribavirin being incorporated at the 5′ end in place of guanosine and preventing the cap methylation step.

Inhibition of host inosine monophosphate dehydrogenase (IMPDH) and subsequent depletion of GTP pool is proposed to be another mechanism of action of ribavirin. IMPDH catalyzes the rate-limiting step where inosine 5′-monophosphate is converted to xanthine monophosphate during guanosine monophosphate (GMP) synthesis. GMP is later converted to guanosine triphoshpate (GTP). Ribavirin monophosphate mimics inosine 5′-monophosphate and acts as a competitive inhibitor of IMPDH. Inhibited de novo synthesis of guanine nucleotides and decreased intracellular GTP pools leads to a decline in viral protein synthesis and limit replication of viral genomes7.

Ribavirin acts as a mutagen in the target virus to cause an 'error catastrophe' due to increased viral mutations. RTP pairs with cytidine triphosphate or uridine triphosphate with equal efficiency and to block HCV RNA elongation. It causes premature termination of nascent HCV RNA and increases mutagenesis by producing defective virions7.

利巴韦林也发挥免疫调节作用f the host to the virus by shifting a Th2 response in favor of a Th1 phenotype. Th2 response and production of type 2 cytokines such as IL-4, IL-5, and IL-10 stimulates the humoral response which enhances immunity toward the virus7. Ribavirin enhanced induction of interferon-related genes, including the interferon-α receptor, and down-regulation of genes involved in interferon inhibition, apoptosis, and hepatic stellate cell activation in vitro6.

Target Actions Organism
AInosine-5'-monophosphate dehydrogenase 1
inhibitor
 Humans
ARNA-directed RNA polymerase L
antagonist
 HPIV-2
AGenome polyprotein
inhibitor
 DENV-2
UInosine-5'-monophosphate dehydrogenase 2 Not Available Humans
URNA-directed RNA polymerase catalytic subunit
inhibitor
 Influenza A virus (strain A/Beijing/11/1956 H1N1)
Absorption

Ribavirin is reported to be rapidly and extensively absorbed following oral administration. The average time to reach Cmax was 2 hours after oral administration of 1200 mg ribavirinLabel. The oral bioavailability is 64% following a single oral dose administration of 600mg ribavirin10.

Volume of distribution

Ribavirin displays a large volume of distributionLabel.

Protein binding

No protein binding reported10.

Metabolism

First and as a step required for activation, ribavirin is phosphorylated intracellularly by adenosine kinase to ribavirin mono-, di-, and triphosphate metabolites. After activation and function, ribavirin undergoes two metabolic pathways where it is reversibly phosphorlyated or degraded via deribosylation and amide hydrolysis to yield a triazole carboxylic acid metabolite. In vitro studies indicate that ribavirin is not a substrate of CYP450 enzymes10.

Route of elimination

The metabolites of ribavirin are renally excreted. After the oral administration of 600mg radiolabeled ribavirin, approximately 61% of the drug was detected in the urine and 12% was detected in the feces. 17% of administered dose was in unchanged form10.

Half-life

The terminal half-life of ribavirin following administration of a single oral dose of 1200 mg is about 120 to 170 hoursLabel.

Clearance

The total apparent clearance rate after a single oral dose administration of 1200 mg ribavirin is 26L/hLabel.

Adverse Effects
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Toxicity

Rivabirin and PEG-Interferon Alfa-2A dual therapy is associated with flu-like symptoms, depression, suicide, insomnia, irritability, relapse of drug abuse/overdose, hepatic decompensation in 2% of HIV co-infected patients and bacterial infections each occurring at a frequency of less than 1%. Ribavirin-induced anemia is a dose-dependent adverse effect where reduced hemoglobin levels can be seen within the first 1-2 weeks in therapy. The mechanism of ribavirin-induced anemia has been shown to involve reductions in reticulocyte counts and erythrocyte Na-K pump activity, and increases in K-Cl cotransport, membrane bound IgG, and C3, and erythrocyte band 36. Oral LD50 in rats is 2700 mg/kg. Intraperitoneal LD50 in mouse is 1300 mg/kg. Potential carcinogenic effects of ribavirin to humans cannot be yet excluded as it demonstrates mutagenic activity in the in vitro mouse lymphoma assay.

Pathways
Not Available
Pharmacogenomic Effects/ADRsBrowse all" title="" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) 类型(年代) Description Details
Interferon lambda-3 --- (C;T)/(G;G)/(G;T)/(T;T) C > T EffectDirectly Studied Patients with this genotype in IFNL3 have a reduced likelihood of achieving sustained virologic response to ribavirin therapy. Details

的相互作用

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction
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Abacavir Ribavirin may increase the hepatotoxic activities of Abacavir.
Aceclofenac Aceclofenac may decrease the excretion rate of Ribavirin which could result in a higher serum level.
Acemetacin Acemetacin可能减少瑞芭的排泄率virin which could result in a higher serum level.
Acetaminophen Acetaminophen may decrease the excretion rate of Ribavirin which could result in a higher serum level.
Acetazolamide Acetazolamide may increase the excretion rate of Ribavirin which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Ribavirin which could result in a higher serum level.
Aclidinium Ribavirin may decrease the excretion rate of Aclidinium which could result in a higher serum level.
Acrivastine Ribavirin may decrease the excretion rate of Acrivastine which could result in a higher serum level.
Acyclovir Acyclovir may decrease the excretion rate of Ribavirin which could result in a higher serum level.
Adefovir dipivoxil Adefovir dipivoxil may decrease the excretion rate of Ribavirin which could result in a higher serum level.
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Food Interactions
  • Avoid alcohol. Ribavirin is used to treat chronic hepatitis C infection; ingesting alcohol may worsen this infection.
  • Take with food. Taking ribavirin with a high-fat meal slows the absorption and increases the AUC and Cmax of ribavirin.

Products

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Product Images
International/Other Brands
Rebretron/Ribamide/Vilona (Valeant)/Viramid (Il Sung)/Virazide (Grossman)
Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image
Copegus Tablet, film coated 200 mg/1 Oral Genentech, Inc. 2002-12-03 2018-01-31 US flag
Ibavyr Tablet 600 mg Oral Pendopharm Division Of Pharmascience Inc 2014-07-14 Not applicable Canada flag
Ibavyr Tablet 400 mg Oral Pendopharm Division Of Pharmascience Inc 2014-07-14 Not applicable Canada flag
Ibavyr Tablet 200 mg Oral Pendopharm Division Of Pharmascience Inc 2015-05-01 Not applicable Canada flag
Moderiba Tablet 200 mg Oral Abbvie 2015-02-17 2018-11-26 Canada flag
Moderiba Tablet 600 mg Oral Abbvie 2015-02-19 2018-07-30 Canada flag
Moderiba Tablet 400 mg Oral Abbvie 2015-02-19 2018-11-26 Canada flag
Rebetol Liquid 40 mg/1mL Oral Merck Sharp & Dohme Corp. 2003-07-29 Not applicable US flag
Rebetol Capsule 200 mg/1 Oral Merck Sharp & Dohme Corp. 1998-06-03 2016-03-31 US flag
Rebetol Solution 40 mg/ml Oral Merck Sharp And Dohme B.V 2016-09-08 Not applicable EU flag
Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image
Moderiba Tablet, film coated 400 mg/1 Oral AbbVie Inc. 2014-01-20 2018-10-31 US flag
Moderiba Tablet, film coated 600 mg/1 Oral AbbVie Inc. 2014-01-20 2019-04-30 US flag
Moderiba Tablet, film coated 200 mg/1 Oral AbbVie Inc. 2014-01-20 2019-05-01 US flag
Ribasphere Tablet 200 mg/1 Oral Remedy Repack 2011-11-18 2014-01-29 US flag
Ribasphere Tablet, film coated 200 mg/1 Oral Kadmon Pharmaceuticals, LLC 2005-12-05 2019-09-30 US flag
Ribasphere Capsule 200 mg/1 Oral Kadmon Pharmaceuticals, LLC 2004-04-07 2019-09-30 US flag
Ribasphere Tablet, film coated 600 mg/1 Oral Kadmon Pharmaceuticals, LLC 2005-12-05 2019-09-30 US flag
Ribasphere Tablet 400 mg/1 Oral Remedy Repack 2010-08-05 2011-08-17 US flag
Ribasphere Tablet, film coated 400 mg/1 Oral Kadmon Pharmaceuticals, LLC 2005-12-05 2019-09-30 US flag
RIBASPHERE RibaPak Tablet 400 mg/1 Oral Kadmon Pharmaceuticals, LLC 2010-01-01 2019-09-30 US flag
Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image
Moderiba Ribavirin(400 mg/1)+ Ribavirin(600 mg/1) Kit Oral AbbVie Inc. 2014-01-20 2018-10-31 US flag
Moderiba Ribavirin(200 mg/1)+ Ribavirin(400 mg/1) Kit Oral AbbVie Inc. 2014-01-20 2018-10-31 US flag
Moderiba Ribavirin(400 mg/1)+ Ribavirin(600 mg/1) Kit Oral AbbVie Inc. 2014-01-20 2018-10-31 US flag
Moderiba Ribavirin(200 mg/1)+ Ribavirin(400 mg/1) Kit Oral AbbVie Inc. 2014-01-20 2018-10-31 US flag
Pegasys Rbv Ribavirin(200 mg / tab)+Peginterferon alfa-2a(180 mcg / mL) Solution; Tablet Oral; Subcutaneous Hoffmann La Roche 2004-05-26 2018-07-10 Canada flag
Pegasys Rbv Ribavirin(200 mg / tab)+Peginterferon alfa-2a(180 mcg / 0.5 mL) Solution; Tablet Oral; Subcutaneous Hoffmann La Roche 2004-05-26 2018-07-10 Canada flag
Pegetron Ribavirin(200 mg / cap)+Peginterferon alfa-2b(50 mcg / 0.5 mL) Capsule; Powder, for solution Oral; Subcutaneous Merck Ltd. 2002-08-13 2017-04-04 Canada flag
Pegetron Ribavirin(200 mg / cap)+Peginterferon alfa-2b(100 mcg / 0.5 mL) Capsule; Powder, for solution Oral; Subcutaneous Merck Ltd. 2002-08-13 2013-01-23 Canada flag
Pegetron Ribavirin(200 mg / cap)+Peginterferon alfa-2b(100 mcg / 0.5 mL) Capsule; Powder, for solution Oral; Subcutaneous Merck Ltd. 2004-09-17 2017-10-05 Canada flag
Pegetron Ribavirin(200 mg / cap)+Peginterferon alfa-2b(150 mcg / 0.5 mL) Capsule; Powder, for solution Oral; Subcutaneous Merck Ltd. 2004-09-17 2017-10-05 Canada flag
Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image
Virazole Ribavirin(0.1 g/1mL) Liquid Intravenous Legacy Pharmaceuticals Switzerland GmbH 2017-12-06 Not applicable US flag

Categories

ATC Codes
J05AP01 — Ribavirin
Drug Categories
Chemical TaxonomyProvided byClassyfire
Description
This compound belongs to the class of organic compounds known as triazole ribonucleosides and ribonucleotides. These are nucleoside derivatives containing a ribose (or deoxyribose) moiety which is N-glycosylated to a triazole. Nucleotides have a phosphate group linked to the C5 carbon of the ribose (or deoxyribose) moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Triazole ribonucleosides and ribonucleotides
Sub Class
Not Available
Direct Parent
Triazole ribonucleosides and ribonucleotides
Alternative Parents
Glycosylamines/Pentoses/2-heteroaryl carboxamides/Triazoles/Tetrahydrofurans/Heteroaromatic compounds/Secondary alcohols/Primary carboxylic acid amides/Oxacyclic compounds/Azacyclic compounds
show 5 more
Substituents
1,2,4-triazole/2-heteroaryl carboxamide/Alcohol/Aromatic heteromonocyclic compound/Azacycle/Azole/Carboxamide group/Carboxylic acid derivative/Glycosyl compound/Heteroaromatic compound
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
monocarboxylic acid amide, aromatic amide, 1-ribosyltriazole (CHEBI:63580)
Affected organisms
  • Hepatitis B virus
  • Hepatitis C virus, RSV and other RNA/DNA viruses

Chemical Identifiers

UNII
49717AWG6K
CAS number
36791-04-5
InChI Key
IWUCXVSUMQZMFG-AFCXAGJDSA-N
InChI
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
IUPAC Name
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide
SMILES
NC(=O)C1=NN(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

References

Synthesis Reference
US3798209
General References
  1. Sidwell RW, Bailey KW, Wong MH, Barnard DL, Smee DF: In vitro and in vivo influenza virus-inhibitory effects of viramidine. Antiviral Res. 2005 Oct;68(1):10-7. [Article]
  2. Sidwell RW, Huffman JH, Khare GP, Allen LB, Witkowski JT, Robins RK: Broad-spectrum antiviral activity of Virazole: 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide. Science. 1972 Aug 25;177(4050):705-6. [Article]
  3. Alvarez D, Dieterich DT, Brau N, Moorehead L, Ball L, Sulkowski MS: Zidovudine use but not weight-based ribavirin dosing impacts anaemia during HCV treatment in HIV-infected persons. J Viral Hepat. 2006 Oct;13(10):683-9. [Article]
  4. Bani-Sadr F, Carrat F, Pol S, Hor R, Rosenthal E, Goujard C, Morand P, Lunel-Fabiani F, Salmon-Ceron D, Piroth L, Pialoux G, Bentata M, Cacoub P, Perronne C: Risk factors for symptomatic mitochondrial toxicity in HIV/hepatitis C virus-coinfected patients during interferon plus ribavirin-based therapy. J Acquir Immune Defic Syndr. 2005 Sep 1;40(1):47-52. [Article]
  5. Myers RP, Shah H, Burak KW, Cooper C, Feld JJ: An update on the management of chronic hepatitis C: 2015 Consensus guidelines from the Canadian Association for the Study of the Liver. Can J Gastroenterol Hepatol. 2015 Jan-Feb;29(1):19-34. Epub 2015 Jan 13. [Article]
  6. Martin P, Jensen DM: Ribavirin in the treatment of chronic hepatitis C. J Gastroenterol Hepatol. 2008 Jun;23(6):844-55. doi: 10.1111/j.1440-1746.2008.05398.x. [Article]
  7. Te HS, Randall G, Jensen DM: Mechanism of action of ribavirin in the treatment of chronic hepatitis C. Gastroenterol Hepatol (N Y). 2007 Mar;3(3):218-25. [Article]
  8. Huggins JW: Prospects for treatment of viral hemorrhagic fevers with ribavirin, a broad-spectrum antiviral drug. Rev Infect Dis. 1989 May-Jun;11 Suppl 4:S750-61. [Article]
  9. American Association for the Study of Liver Diseases; Infectious Diseases Society of America. HCV guidance. http://hcvguidelines.org. Accessed June 12, 2017. [Link]
  10. FDA Approved Drug Products: Rebetol (ribavirin) oral capsules [Link]
Human Metabolome Database
HMDB0014949
KEGG Drug
D00423
PubChem Compound
37542
PubChem Substance
46505883
ChemSpider
34439
BindingDB
50154375
RxNav
9344
ChEBI
63580
ChEMBL
CHEMBL1643
ZINC
ZINC000001035331
Therapeutic Targets Database
DNC001210
PharmGKB
PA451241
PDBe Ligand
RBV
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ribavirin
PDB Entries
3sfu/4pb1/5axd
FDA label
Download (1.25 MB)
MSDS
Download (350 KB)

Clinical Trials

Clinical TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
4 Active Not Recruiting Treatment Hepatitis C Virus (HCV) Infection 1
4 Completed Basic Science Chronic Hepatitis C Virus (HCV) Infection/Liver Disease/Viral Disease 1
4 Completed Diagnostic Chronic Hepatitis C Virus (HCV) Infection 1
4 Completed Prevention Chronic Hepatitis C Virus (HCV) Infection 1
4 Completed Prevention Hepatitis C Virus (HCV) Infection 1
4 Completed Prevention Hepatitis C Virus (HCV) Infection/Liver Transplantation 1
4 Completed Supportive Care Chronic Hepatitis C Virus (HCV) Infection 1
4 Completed Treatment Alcohol Dependency/Hepatitis C Virus (HCV) Infection/Liver Disease/Substance Abuse 1
4 Completed Treatment Anemia 1
4 Completed Treatment Antiviral Agents/Chronic Liver Diseases (CLD)/Hepatitis C Virus (HCV) Infection/Therapeutic Uses/Virus Hepatitis 1

Pharmacoeconomics

Manufacturers
  • Schering plough research institute
  • Three rivers pharmaceuticals llc
  • Aurobindo pharma ltd
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Zydus pharmaceuticals usa inc
  • Valeant pharmaceuticals international
  • Schering corp
  • Hoffmann la roche inc
Packagers
  • Amerisource Health Services Corp.
  • Aurobindo Pharma Ltd.
  • Ben Venue Laboratories Inc.
  • Cadila Healthcare Ltd.
  • DSM Corp.
  • F Hoffmann-La Roche Ltd.
  • Legacy Pharmaceuticals Packaging LLC
  • Mallinckrodt Inc.
  • Medisca Inc.
  • Par Pharmaceuticals
  • Patheon Inc.
  • Physicians Total Care Inc.
  • Prx Pharmaceuticals
  • Richmond Pharmacy
  • Sandoz
  • Schering Corp.
  • Schering-Plough Inc.
  • Teva Pharmaceutical Industries Ltd.
  • Three Rivers Pharmaceuticals LLC
  • Valeant Ltd.
  • Warrick Pharmaceuticals Corp.
  • Zydus Pharmaceuticals
Dosage Forms
Form Route Strength
Tablet, film coated Oral
Tablet, film coated Oral 400 MG
Tablet Oral 600 mg
Tablet, film coated Oral 400 mg/1
Tablet, film coated Oral 600 MG
Tablet, film coated Oral 600 mg/1
Tablet, film coated Oral 200 mg
Solution; tablet Oral; Subcutaneous
Capsule; powder, for solution Oral; Subcutaneous
Liquid Oral 40 mg/1mL
Solution Oral 40 mg/ml
Capsule Oral 200 mg
Capsule; kit; liquid Oral; Subcutaneous
Tablet Oral 200 mg/1
Kit Oral
Kit; tablet Oral
Tablet Oral 400 mg/1
Tablet Oral 600 mg/1
Capsule Oral 200 mg/1
Powder, for solution Respiratory (inhalation) 6 g/1
Tablet, coated Oral 200 mg/1
Tablet, film coated Oral 200 mg/1
Tablet, film coated Oral 500 mg/1
Capsule Oral
Capsule, coated Oral 200 mg
Aerosol; powder, for solution Respiratory (inhalation) 6 g / vial
Liquid Intravenous 0.1 g/1mL
Powder, for solution Respiratory (inhalation)
Injection, powder, for solution Parenteral 6 g
Tablet, coated Oral 200 mg
Tablet Oral 200 mg
Tablet Oral 400 mg
Prices
Unit description Cost Unit
Virazole 6 gm vial 4512.21USD vial
Ribatab 600 mg tablet 32.01USD tablet
Ribasphere 600 mg tablet 24.88USD tablet
Ribavirin 600 mg tablet 24.88USD tablet
Ribatab 400 mg tablet 21.34USD tablet
Ribavirin 500 mg tablet 20.74USD tablet
Ribasphere 400 mg tablet 16.59USD tablet
Ribavirin 400 mg tablet 16.59USD tablet
Copegus 200 mg tablet 15.19USD tablet
Rebetol 200 mg capsule 10.81USD capsule
Ribasphere 200 mg capsule 10.33USD capsule
Ribavirin 200 mg capsule 10.33USD capsule
Ribasphere 200 mg tablet 8.29USD tablet
Ribavirin 200 mg tablet 8.29USD tablet
Ribavirin powder 3.21USD g
Rebetol 40 mg/ml Solution 2.42USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region
CA2365412 No 2002-09-17 2018-12-21 Canada flag
CA2287056 No 2000-08-15 2018-12-21 Canada flag
US6150337 No 2000-11-21 2017-11-21 US flag
US6172046 Yes 2001-01-09 2018-03-21 US flag
US6177074 Yes 2001-01-23 2017-05-01 US flag
US6461605 Yes 2002-10-08 2017-05-01 US flag
US6472373 Yes 2002-10-29 2018-03-21 US flag
US6524570 Yes 2003-02-25 2017-05-01 US flag
US6790837 Yes 2004-09-14 2023-10-05 US flag

Properties

State
Solid
Experimental Properties
Property Value Source
melting point (°C) 174-176 °C MSDS
water solubility 可溶性 MSDS
logP -1.85 MSDS
Predicted Properties
Property Value Source
Water Solubility 33.2 mg/mL ALOGPS
logP -1.9 ALOGPS
logP -2.8 Chemaxon
logS -0.87 ALOGPS
pKa (Strongest Acidic) 11.88 Chemaxon
pKa (Strongest Basic) -1.2 Chemaxon
Physiological Charge 0 Chemaxon
Hydrogen Acceptor Count 7 Chemaxon
Hydrogen Donor Count 4 Chemaxon
Polar Surface Area 143.72 Å2 Chemaxon
Rotatable Bond Count 3 Chemaxon
Refractivity 64.57 m3·mol-1 Chemaxon
Polarizability 22.18 Å3 Chemaxon
Number of Rings 2 Chemaxon
Bioavailability 1 Chemaxon
Rule of Five Yes Chemaxon
Ghose Filter No Chemaxon
Veber's Rule No Chemaxon
MDDR-like Rule No Chemaxon
Predicted ADMET Features
Property Value Probability
Human Intestinal Absorption + 0.9852
Blood Brain Barrier + 0.9381
Caco-2 permeable - 0.7742
P-glycoprotein substrate Non-substrate 0.7715
P-glycoprotein inhibitor I Non-inhibitor 0.9507
P-glycoprotein inhibitor II Non-inhibitor 0.964
肾有机阳离子转运体 Non-inhibitor 0.9574
CYP450 2C9 substrate Non-substrate 0.8329
CYP450 2D6 substrate Non-substrate 0.8426
CYP450 3A4 substrate Non-substrate 0.6011
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 inhibitor Non-inhibitor 0.9462
CYP450 2D6 inhibitor Non-inhibitor 0.9442
CYP450 2C19 inhibitor Non-inhibitor 0.9095
CYP450 3A4 inhibitor Non-inhibitor 0.9535
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9845
Ames test Non AMES toxic 0.9133
Carcinogenicity Non-carcinogens 0.9025
Biodegradation Not ready biodegradable 0.7406
Rat acute toxicity 1.9876 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9948
hERG inhibition (predictor II) Non-inhibitor 0.919
ADMET data is predicted usingadmetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Spectrum Spectrum Type Splash Key
Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available
预测MS / MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
预测MS / MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
预测MS / MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
预测MS / MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
预测MS / MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
预测MS / MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
LC-MS/MS Spectrum - LC-ESI-QFT , negative LC-MS/MS splash10-03di-0900000000-92e2bd11ded2c95f3fbd
LC-MS/MS Spectrum - LC-ESI-QFT , negative LC-MS/MS splash10-03di-0900000000-109ebb69f722bb3a92d7
LC-MS/MS Spectrum - LC-ESI-QFT , negative LC-MS/MS splash10-03di-2900000000-c0d63d0633c304d466ca
LC-MS/MS Spectrum - LC-ESI-QFT , negative LC-MS/MS splash10-03xr-5900000000-c6f13aea6e263f2557f4
LC-MS/MS Spectrum - LC-ESI-QFT , negative LC-MS/MS splash10-02t9-9500000000-cefa4afc53cf92b724c3
LC-MS/MS Spectrum - LC-ESI-QFT , negative LC-MS/MS splash10-014i-9200000000-3a87882b304f3a9c9995
LC-MS/MS Spectrum - LC-ESI-QFT , positive LC-MS/MS splash10-03di-0900000000-d5e98a470d0e674937d2
LC-MS/MS Spectrum - LC-ESI-QFT , positive LC-MS/MS splash10-03di-0900000000-c659efd26af31b3b98dc
LC-MS/MS Spectrum - LC-ESI-QFT , positive LC-MS/MS splash10-03di-1900000000-56c00c62af197ae8eecb
LC-MS/MS Spectrum - LC-ESI-QFT , positive LC-MS/MS splash10-03di-2900000000-aa387f940aedc4b69874
LC-MS/MS Spectrum - LC-ESI-QFT , positive LC-MS/MS splash10-03di-3900000000-795b88d3d651082dccb4

Targets

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Details 1.Inosine-5'-monophosphate dehydrogenase 1
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Rna binding
Specific Function
Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore pl...
Gene Name
IMPDH1
Uniprot ID
P20839
Uniprot Name
Inosine-5'-monophosphate dehydrogenase 1
Molecular Weight
55405.365 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  2. Gish RG: Treating HCV with ribavirin analogues and ribavirin-like molecules. J Antimicrob Chemother. 2006 Jan;57(1):8-13. Epub 2005 Nov 17. [Article]
  3. McHutchison JG, Shiffman ML, Cheung RC, Gordon SC, Wright TL, Pottage JC Jr, McNair L, Ette E, Moseley S, Alam J: A randomized, double-blind, placebo-controlled dose-escalation trial of merimepodib (VX-497) and interferon-alpha in previously untreated patients with chronic hepatitis C. Antivir Ther. 2005;10(5):635-43. [Article]
  4. Leyssen P, De Clercq E, Neyts J: The anti-yellow fever virus activity of ribavirin is independent of error-prone replication. Mol Pharmacol. 2006 Apr;69(4):1461-7. Epub 2006 Jan 18. [Article]
Details 2.RNA-directed RNA polymerase L
Kind
Protein
Organism
HPIV-2
Pharmacological action
Yes
Actions
Antagonist
General Function
Rna-directed rna polymerase activity
Specific Function
Displays RNA-directed RNA polymerase, mRNA guanylyl transferase, mRNA (guanine-N(7)-)-methyltransferase and poly(A) synthetase activities. The viral mRNA guanylyl transferase displays a different b...
Gene Name
L
Uniprot ID
P26676
Uniprot Name
RNA-directed RNA polymerase L
Molecular Weight
256380.115 Da
References
  1. Eriksson B, Helgstrand E, Johansson NG, Larsson A, Misiorny A, Noren JO, Philipson L, Stenberg K, Stening G, Stridh S, Oberg B: Inhibition of influenza virus ribonucleic acid polymerase by ribavirin triphosphate. Antimicrob Agents Chemother. 1977 Jun;11(6):946-51. doi: 10.1128/aac.11.6.946. [Article]
Details 3.Genome polyprotein
Kind
Protein
Organism
DENV-2
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Ribavirin's effects on genome polyprotein may stem from its inhibition of the mRNA 2'-O-methyltransferase domain.
General Function
Structural molecule activity
Specific Function
衣壳蛋白C self-assembles to form an icosahedral capsid about 30 nm in diameter. The capsid encapsulates the genomic RNA.prM acts as a chaperone for envelope protein E during intracellular vi...
Gene Name
Not Available
Uniprot ID
P12823
Uniprot Name
Genome polyprotein
Molecular Weight
379216.195 Da
References
  1. Benarroch D, Egloff MP, Mulard L, Guerreiro C, Romette JL, Canard B: A structural basis for the inhibition of the NS5 dengue virus mRNA 2'-O-methyltransferase domain by ribavirin 5'-triphosphate. J Biol Chem. 2004 Aug 20;279(34):35638-43. doi: 10.1074/jbc.M400460200. Epub 2004 May 19. [Article]
  2. Chang J, Schul W,黄油TD,犬吠,刘B,吴,Lakshminarayana SB, Alonzi D, Reinkensmeier G, Pan X, Qu X, Weidner JM, Wang L, Yu W, Borune N, Kinch MA, Rayahin JE, Moriarty R, Xu X, Shi PY, Guo JT, Block TM: Combination of alpha-glucosidase inhibitor and ribavirin for the treatment of dengue virus infection in vitro and in vivo. Antiviral Res. 2011 Jan;89(1):26-34. doi: 10.1016/j.antiviral.2010.11.002. Epub 2010 Nov 10. [Article]
  3. Pires de Mello CP, Drusano GL, Rodriquez JL, Kaushik A, Brown AN: Antiviral Effects of Clinically-Relevant Interferon-alpha and Ribavirin Regimens against Dengue Virus in the Hollow Fiber Infection Model (HFIM). Viruses. 2018 Jun 9;10(6). pii: v10060317. doi: 10.3390/v10060317. [Article]
Details 4.Inosine-5'-monophosphate dehydrogenase 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Rna binding
Specific Function
Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore pl...
Gene Name
IMPDH2
Uniprot ID
P12268
Uniprot Name
Inosine-5'-monophosphate dehydrogenase 2
Molecular Weight
55804.495 Da
References
  1. Markland W, McQuaid TJ, Jain J, Kwong AD: Broad-spectrum antiviral activity of the IMP dehydrogenase inhibitor VX-497: a comparison with ribavirin and demonstration of antiviral additivity with alpha interferon. Antimicrob Agents Chemother. 2000 Apr;44(4):859-66. [Article]
  2. Shah CP, Kharkar PS: Newer human inosine 5'-monophosphate dehydrogenase 2 (hIMPDH2) inhibitors as potential anticancer agents. J Enzyme Inhib Med Chem. 2018 Dec;33(1):972-977. doi: 10.1080/14756366.2018.1474211. [Article]
Details 5.RNA-directed RNA polymerase catalytic subunit
Kind
Protein
Organism
Influenza A virus (strain A/Beijing/11/1956 H1N1)
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Rna-directed rna polymerase activity
Specific Function
RNA-dependent RNA polymerase which is responsible for replication and transcription of virus RNA segments. The transcription of viral mRNAs occurs by a unique mechanism called cap-snatching. 5' met...
Gene Name
PB1
Uniprot ID
P16502
Uniprot Name
RNA-directed RNA polymerase catalytic subunit
Molecular Weight
86534.5 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Bougie I, Bisaillon M: Initial binding of the broad spectrum antiviral nucleoside ribavirin to the hepatitis C virus RNA polymerase. J Biol Chem. 2003 Dec 26;278(52):52471-8. Epub 2003 Oct 16. [Article]

Enzymes

Details 1.Cytosolic purine 5'-nucleotidase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Modulator
General Function
Nucleotide binding
Specific Function
May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-mo...
Gene Name
NT5C2
Uniprot ID
P49902
Uniprot Name
Cytosolic purine 5'-nucleotidase
Molecular Weight
64969.2 Da
References
  1. Wu JZ, Larson G, Walker H, Shim JH, Hong Z: Phosphorylation of ribavirin and viramidine by adenosine kinase and cytosolic 5'-nucleotidase II: Implications for ribavirin metabolism in erythrocytes. Antimicrob Agents Chemother. 2005 Jun;49(6):2164-71. [Article]
  2. Wallden K, Nordlund P: Structural basis for the allosteric regulation and substrate recognition of human cytosolic 5'-nucleotidase II. J Mol Biol. 2011 May 13;408(4):684-96. doi: 10.1016/j.jmb.2011.02.059. Epub 2011 Mar 17. [Article]
Details 2.腺苷酸激酶
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Activator
General Function
Poly(a) rna binding
Specific Function
ATP依赖的腺苷磷酸化and other related nucleoside analogs to monophosphate derivatives. Serves as a potential regulator of concentrations of extracellular adenosine and intrac...
Gene Name
ADK
Uniprot ID
P55263
Uniprot Name
腺苷酸激酶
Molecular Weight
40545.075 Da
References
  1. Wu JZ, Larson G, Walker H, Shim JH, Hong Z: Phosphorylation of ribavirin and viramidine by adenosine kinase and cytosolic 5'-nucleotidase II: Implications for ribavirin metabolism in erythrocytes. Antimicrob Agents Chemother. 2005 Jun;49(6):2164-71. [Article]
  2. Kumarapperuma SC, Sun Y, Jeselnik M, Chung K, Parker WB, Jonsson CB, Arterburn JB: Structural effects on the phosphorylation of 3-substituted 1-beta-D-ribofuranosyl-1,2,4-triazoles by human adenosine kinase. Bioorg Med Chem Lett. 2007 Jun 1;17(11):3203-7. Epub 2007 Mar 12. [Article]

Transporters

Details 1.Solute carrier family 28 member 3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Pyrimidine- and adenine-specific:sodium symporter activity
Specific Function
Sodium-dependent, pyrimidine- and purine-selective. Involved in the homeostasis of endogenous nucleosides. Exhibits the transport characteristics of the nucleoside transport system cib or N3 subtyp...
Gene Name
SLC28A3
Uniprot ID
Q9HAS3
Uniprot Name
Solute carrier family 28 member 3
Molecular Weight
76929.61 Da
References
  1. Yamamoto T, Sugawara M, Kikukawa T, Miyauchi S, Yamaguchi M, Tero A, Takagi S, Nakagaki T: Kinetic study of anti-viral ribavirin uptake mediated by hCNT3 and hENT1 in Xenopus laevis oocytes. Biophys Chem. 2010 Mar;147(1-2):59-65. doi: 10.1016/j.bpc.2009.12.012. Epub 2010 Jan 6. [Article]
Details 2.Equilibrative nucleoside transporter 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Nucleoside transmembrane transporter activity
Specific Function
Mediates both influx and efflux of nucleosides across the membrane (equilibrative transporter). It is sensitive (ES) to low concentrations of the inhibitor nitrobenzylmercaptopurine riboside (NBMPR...
Gene Name
SLC29A1
Uniprot ID
Q99808
Uniprot Name
Equilibrative nucleoside transporter 1
Molecular Weight
50218.805 Da
References
  1. Yamamoto T, Sugawara M, Kikukawa T, Miyauchi S, Yamaguchi M, Tero A, Takagi S, Nakagaki T: Kinetic study of anti-viral ribavirin uptake mediated by hCNT3 and hENT1 in Xenopus laevis oocytes. Biophys Chem. 2010 Mar;147(1-2):59-65. doi: 10.1016/j.bpc.2009.12.012. Epub 2010 Jan 6. [Article]
  2. Fukuchi Y, Furihata T, Hashizume M, Iikura M, Chiba K: Characterization of ribavirin uptake systems in human hepatocytes. J Hepatol. 2010 Apr;52(4):486-92. doi: 10.1016/j.jhep.2010.01.011. Epub 2010 Feb 4. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 19, 2023 23:50