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Identification
NameRibavirin
Accession NumberDB00811  (APRD00081, EXPT02825, DB01693)
TypeSmall Molecule
GroupsApproved
Description

A nucleoside antimetabolite antiviral agent that blocks nucleic acid synthesis and is used against both RNA and DNA viruses. [PubChem]

Structure
Thumb
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 Identifiers
  • ICN 1229
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Copegustablet, film coated200 mg/1oralGenentech, Inc.2002-12-03Not applicableUs
Ibavyrtablet200 mgoralPendopharm Division Of De Pharmascience Inc2015-05-01Not applicableCanada
Ibavyrtablet600 mgoralPendopharm Division Of De Pharmascience Inc2014-07-14Not applicableCanada
Ibavyrtablet400 mgoralPendopharm Division Of De Pharmascience Inc2014-07-14Not applicableCanada
Moderibatablet600 mgoralAbbvie Corporation2015-02-19Not applicableCanada
Moderibatablet400 mgoralAbbvie Corporation2015-02-19Not applicableCanada
Moderibatablet200 mgoralAbbvie Corporation2015-02-17Not applicableCanada
Rebetolcapsule200 mg/1oralMerck Sharp & Dohme Corp.1998-06-03Not applicableUs
Rebetolcapsule200 mg/1oralMerck Sharp & Dohme Corp.1998-06-03Not applicableUs
Rebetolliquid40 mg/mLoralMerck Sharp & Dohme Corp.2003-07-29Not applicableUs
Rebetolcapsule200 mg/1oralMerck Sharp & Dohme Corp.1998-06-03Not applicableUs
Virazoleaerosol; powder for solution6 ginhalationValeant Canada Lp Valeant Canada S.E.C.1996-12-05Not applicableCanada
Virazolepowder, for solution6 g/1respiratory (inhalation)Valeant Pharmaceuticals North America LLC1986-01-01Not applicableUs
Virazole Pws 6gm/vialaerosol; powder for solution6 ginhalationViratek Inc.1986-12-311997-08-08Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Moderibatablet, film coated200 mg/1oralAbb Vie Inc.2014-01-20Not applicableUs
Moderibatablet, film coated600 mg/1oralAbb Vie Inc.2014-01-20Not applicableUs
ModeribakitAbb Vie Inc.2014-01-20Not applicableUs
Moderibatablet, film coated400 mg/1oralAbb Vie Inc.2014-01-20Not applicableUs
ModeribakitAbb Vie Inc.2014-01-20Not applicableUs
Ribaspheretablet, film coated600 mg/1oralKadmon Pharmaceuticals, LLC2005-12-05Not applicableUs
Ribaspheretablet, film coated400 mg/1oralKadmon Pharmaceuticals, LLC2005-12-05Not applicableUs
Ribaspheretablet200 mg/1oralREMEDYREPACK INC.2011-11-30Not applicableUs
Ribaspheretablet, film coated200 mg/1oralKadmon Pharmaceuticals, LLC2005-12-05Not applicableUs
Ribaspheretablet400 mg/1oralREMEDYREPACK INC.2011-08-18Not applicableUs
Ribaspherecapsule200 mg/1oralKadmon Pharmaceuticals, LLC2004-04-07Not applicableUs
Ribasphere Ribapaktablet600 mg/1oralKadmon Pharmaceuticals, LLC2010-01-01Not applicableUs
Ribasphere RibapakkitKadmon Pharmaceuticals, LLC2010-01-01Not applicableUs
Ribasphere Ribapaktablet400 mg/1oralKadmon Pharmaceuticals, LLC2010-01-01Not applicableUs
Ribasphere RibapakkitKadmon Pharmaceuticals, LLC2012-06-01Not applicableUs
Ribavirintablet, film coated600 mg/1oralRichmond Pharmaceuticals, Inc.2008-06-01Not applicableUs
Ribavirincapsule200 mg/1oralAmerican Health Packaging2006-11-30Not applicableUs
Ribavirintablet, film coated200 mg/1oralCadila Healthcare Limited2005-12-05Not applicableUs
Ribavirincapsule200 mg/1oralSandoz Inc2004-04-06Not applicableUs
Ribavirincapsule200 mg/1oralTeva Pharmaceuticals USA Inc2004-10-042015-11-30Us
Ribavirincapsule200 mg/1oralAurobindo Pharma Limited2009-09-17Not applicableUs
Ribavirintablet, film coated400 mg/1oralRichmond Pharmaceuticals, Inc.2008-06-01Not applicableUs
Ribavirincapsule200 mg/1oralZydus Pharmaceuticals (USA) Inc.2006-01-25Not applicableUs
Ribavirintablet, film coated200 mg/1oralAurobindo Pharma Limited2009-09-17Not applicableUs
Ribavirintablet, coated200 mg/1oralTeva Pharmaceuticals USA Inc2005-12-052016-02-06Us
Ribavirintablet, film coated200 mg/1oralRichmond Pharmaceuticals, Inc.2008-06-01Not applicableUs
Ribavirintablet, film coated600 mg/1oralZydus Pharmaceuticals (USA) Inc.2005-12-05Not applicableUs
Ribavirintablet, film coated500 mg/1oralCadila Healthcare Limited2005-12-05Not applicableUs
Ribavirintablet, film coated200 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Ribavirintablet, film coated500 mg/1oralZydus Pharmaceuticals (USA) Inc.2005-12-05Not applicableUs
Ribavirintablet, film coated400 mg/1oralCadila Healthcare Limited2005-12-05Not applicableUs
Ribavirincapsule200 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Ribavirintablet, film coated200 mg/1oralSandoz Inc2006-10-03Not applicableUs
Ribavirintablet, film coated400 mg/1oralZydus Pharmaceuticals (USA) Inc.2005-12-05Not applicableUs
Ribavirincapsule200 mg/1oralCadila Healthcare Limited2006-01-25Not applicableUs
Ribavirintablet, film coated200 mg/1oralAmerican Health Packaging2006-11-302015-12-29Us
Ribavirincapsule200 mg/1oralRichmond Pharmaceuticals, Inc.2007-11-01Not applicableUs
Ribavirintablet, film coated200 mg/1oralZydus Pharmaceuticals (USA) Inc.2005-12-05Not applicableUs
Ribavirintablet, film coated600 mg/1oralCadila Healthcare Limited2005-12-05Not applicableUs
Ribavirincapsule200 mg/1oralAv Kare, Inc.2014-01-172015-12-29Us
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
RebretronNot Available
RibamideNot Available
VilonaValeant
ViramidIl Sung
VirazideGrossman
Brand mixtures
NameLabellerIngredients
Pegasys RbvHoffmann La Roche Limited
PegetronMerck Canada Inc
Rebetron Ready To Use Solution (albumin(human)free) (6000000 Iu/ml and 200mg Capsules)Schering Plough Canada Inc
Rebetron Solution (albumin (human) Free) (18 Miu Multi-dose Pen / 200mg Capsules)Schering Plough Canada Inc
Victrelis TripleMerck Canada Inc
Salts
Name/CASStructureProperties
Ribavirin monophosphate
40925-28-8
Thumb
  • InChI Key: SDWIOXKHTFOULX-AFCXAGJDSA-N
  • Monoisotopic Mass: 324.047099924
  • Average Mass: 324.1846
DBSALT001876
Categories
UNII49717AWG6K
CAS number36791-04-5
WeightAverage: 244.2047
Monoisotopic: 244.080769514
Chemical FormulaC8H12N4O5
InChI KeyInChIKey=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[[email protected]](CO)[C@@H](O)[[email protected]]1O
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassTriazole ribonucleosides and ribonucleotides
Sub ClassNot Available
Direct ParentTriazole ribonucleosides and ribonucleotides
Alternative Parents
Substituents
  • N-ribosyl-1,2,4-triazole
  • N-glycosyl compound
  • Glycosyl compound
  • 1,2,4-triazole carboxylic acid or derivatives
  • 1,2,4-triazole carboxamide
  • Monosaccharide
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Triazole
  • Oxolane
  • Azole
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of chronic hepatitis C and for respiratory syncytial virus (RSV).
PharmacodynamicsRibavirin is an anti-viral drug active against a number of DNA and 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 it's resemblence to building blocks of the RNA molecules. The oral form is used in the treatment of hepatitis C, in combination with interferon drugs. The aerosol form is used to treat respiratory syncytial virus-related diseases in children. The primary serious adverse effect of ribavirin is hemolytic anemia, which may worsen preexisting cardiac disease.
Mechanism of actionRibavirin is readily phosphorylated intracellularly by adenosine kinase to ribavirin mono-, di-, and triphosphate metabolites. Ribavirin triphosphate (RTP) is a potent competitive inhibitor of inosine monophosphate (IMP) dehydrogenase, viral RNA polymerase and messenger RNA (mRNA) guanylyltransferase (viral) and can be incorporated into RNA in RNA viral species.. Guanylyltranserase inhibition stops the capping of mRNA. These diverse effects result in a marked reduction of intracellular guanosine triphosphate (GTP) pools and inhibition of viral RNA and protein synthesis. Ribavirin is also incorporated into the viral genome causing lethal mutagenesis and a subsequent decrease in specific viral infectivity.
Related Articles
AbsorptionRapidly and extensively absorbed following oral administration. However, due to first-pass metabolism, the absolute bioavailability averages 64%.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic. Results of in vitro studies using both human and rat liver microsome preparations indicated little or no cytochrome P450 enzyme-mediated metabolism of ribavirin, with minimal potential for P450 enzyme-based drug interactions. Ribavirin has two pathways of metabolism: (1) a reversible phosphorylation pathway in nucleated cells; and (2) a degradative pathway involving deribosylation and amide hydrolysis to yield a triazole carboxylic acid metabolite.

Route of eliminationNot Available
Half life9.5 hours
Clearance
  • Apparent cl=26 L/h [A single oral dose]
ToxicitySide effects include "flu-like" symptoms, such as headache, fatigue, myalgia, and fever. The LD50 in mice is 2 g/kg orally and is associated with hypoactivity and gastrointestinal symptoms (estimated human equivalent dose of 0.17 g/kg, based on body surface area conversion).
Affected organisms
  • Hepatitis C virus, RSV and other RNA/DNA viruses
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9852
Blood Brain Barrier+0.9381
Caco-2 permeable-0.7742
P-glycoprotein substrateNon-substrate0.7715
P-glycoprotein inhibitor INon-inhibitor0.9507
P-glycoprotein inhibitor IINon-inhibitor0.964
Renal organic cation transporterNon-inhibitor0.9574
CYP450 2C9 substrateNon-substrate0.8329
CYP450 2D6 substrateNon-substrate0.8426
CYP450 3A4 substrateNon-substrate0.6011
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9462
CYP450 2D6 inhibitorNon-inhibitor0.9442
CYP450 2C19 inhibitorNon-inhibitor0.9095
CYP450 3A4 inhibitorNon-inhibitor0.9535
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9845
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9025
BiodegradationNot ready biodegradable0.7406
Rat acute toxicity1.9876 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9948
hERG inhibition (predictor II)Non-inhibitor0.919
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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
Dosage forms
FormRouteStrength
Tablet, film coatedoral200 mg/1
Tabletoral400 mg
Tabletoral600 mg
Kit
Tabletoral200 mg
Tablet, film coatedoral400 mg/1
Tablet, film coatedoral600 mg/1
Solution; tabletoral; subcutaneous
Capsule; powder for solutionoral; subcutaneous
Capsuleoral200 mg/1
Liquidoral40 mg/mL
Kit; liquid; capsuleoral; subcutaneous
Tabletoral200 mg/1
Tabletoral400 mg/1
Tabletoral600 mg/1
Tablet, coatedoral200 mg/1
Tablet, film coatedoral500 mg/1
Aerosol; powder for solutioninhalation6 g
Powder, for solutionrespiratory (inhalation)6 g/1
Prices
Unit descriptionCostUnit
Virazole 6 gm vial4512.21USD vial
Ribatab 600 mg tablet32.01USD tablet
Ribasphere 600 mg tablet24.88USD tablet
Ribavirin 600 mg tablet24.88USD tablet
Ribatab 400 mg tablet21.34USD tablet
Ribavirin 500 mg tablet20.74USD tablet
Ribasphere 400 mg tablet16.59USD tablet
Ribavirin 400 mg tablet16.59USD tablet
Copegus 200 mg tablet15.19USD tablet
Rebetol 200 mg capsule10.81USD capsule
Ribasphere 200 mg capsule10.33USD capsule
Ribavirin 200 mg capsule10.33USD capsule
Ribasphere 200 mg tablet8.29USD tablet
Ribavirin 200 mg tablet8.29USD tablet
Ribavirin powder3.21USD g
Rebetol 40 mg/ml Solution2.42USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2287056 No2000-08-152018-12-21Canada
CA2365412 No2002-09-172018-12-21Canada
US6150337 No1997-11-212017-11-21Us
US6172046 Yes1998-03-212018-03-21Us
US6177074 Yes1997-05-012017-05-01Us
US6461605 Yes1997-05-012017-05-01Us
US6472373 Yes1998-03-212018-03-21Us
US6524570 Yes1997-05-012017-05-01Us
US6790837 Yes2003-10-052023-10-05Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point174-176 °CNot Available
water solubility142 mg/mL (max, at 25 °C)Not Available
logP-1.85BIOBYTE (1995)
Predicted Properties
PropertyValueSource
Water Solubility33.2 mg/mLALOGPS
logP-1.9ALOGPS
logP-2.8ChemAxon
logS-0.87ALOGPS
pKa (Strongest Acidic)11.88ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area143.72 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity64.57 m3·mol-1ChemAxon
Polarizability22.18 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
References
Synthesis Reference

DrugSyn.org

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. [PubMed:16087250 ]
  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. [PubMed:4340949 ]
  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. [PubMed:16970600 ]
  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. [PubMed:16123681 ]
External Links
ATC CodesJ05AB04
AHFS Codes
  • 08:18.32
PDB Entries
FDA labelDownload (2.17 MB)
MSDSDownload (39.3 KB)
Interactions
Drug Interactions
Drug
AbacavirRibavirin may increase the hepatotoxic activities of Abacavir.
Adefovir DipivoxilRibavirin may increase the hepatotoxic activities of Adefovir Dipivoxil.
AzathioprineThe serum concentration of the active metabolites of Azathioprine can be increased when Azathioprine is used in combination with Ribavirin.
DidanosineThe risk or severity of adverse effects can be increased when Ribavirin is combined with Didanosine.
EmtricitabineRibavirin may increase the hepatotoxic activities of Emtricitabine.
EntecavirRibavirin may increase the hepatotoxic activities of Entecavir.
Interferon alfa-n3The risk or severity of adverse effects can be increased when Interferon alfa-n3 is combined with Ribavirin.
Interferon alfacon-1The risk or severity of adverse effects can be increased when Interferon alfacon-1 is combined with Ribavirin.
LamivudineRibavirin may increase the hepatotoxic activities of Lamivudine.
Peginterferon alfa-2aThe risk or severity of adverse effects can be increased when Peginterferon alfa-2a is combined with Ribavirin.
Peginterferon alfa-2bThe risk or severity of adverse effects can be increased when Peginterferon alfa-2b is combined with Ribavirin.
StavudineRibavirin may increase the hepatotoxic activities of Stavudine.
ZidovudineThe risk or severity of adverse effects can be increased when Zidovudine is combined with Ribavirin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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 plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in t...
Gene Name:
IMPDH1
Uniprot ID:
P20839
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. [PubMed:11752352 ]
  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. [PubMed:16293677 ]
  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. [PubMed:16152757 ]
  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. [PubMed:16421290 ]
Kind
Protein
Organism
Human
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 plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in t...
Gene Name:
IMPDH2
Uniprot ID:
P12268
Molecular Weight:
55804.495 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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
activator
General Function:
Poly(a) rna binding
Specific Function:
ATP dependent phosphorylation of adenosine and other related nucleoside analogs to monophosphate derivatives. Serves as a potential regulator of concentrations of extracellular adenosine and intracellular adenine nucleotides.
Gene Name:
ADK
Uniprot ID:
P55263
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. [PubMed:15917509 ]
  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. [PubMed:17379518 ]
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 biochemical reaction than the cellular enzyme. The template is composed of the viral RNA tightly encapsidated by the nucleoprotein (N). Functions either as transcriptase or as replicase. The transcript...
Gene Name:
L
Uniprot ID:
P26676
Molecular Weight:
256380.115 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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
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' methylated caps of cellular mRNAs are cleaved after 10-13 nucleotides by PA. In turn, these short capped RNAs are used as primers by PB1 for transcription of viral mRNAs. During virus replication, PB1 in...
Gene Name:
PB1
Uniprot ID:
P16502
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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  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. [PubMed:14563844 ]
6. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
unknown
Actions
incorporation into and destabilization
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  3. Ren FY, Jin H, Piao XX, Piao FS: Ribavirin and IFN-alpha combination therapy induces CD4+ T-cell proliferation and Th1 cytokine secretion in patients with chronic hepatitis B. World J Gastroenterol. 2007 Nov 7;13(41):5440-5. [PubMed:17907286 ]
  4. Crotty S, Cameron C, Andino R: Ribavirin's antiviral mechanism of action: lethal mutagenesis? J Mol Med (Berl). 2002 Feb;80(2):86-95. Epub 2001 Dec 4. [PubMed:11907645 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
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'-monophosphate (IMP) and other purine nucleotides.
Gene Name:
NT5C2
Uniprot ID:
P49902
Molecular Weight:
64969.2 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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Zinc ion binding
Specific Function:
By generating PPi, plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. PPi inhibits mineralization by binding to nascent hydroxyapatite (HA) crystals, thereby preventing further growth of these crystals. Preferentially hydrolyzes ATP, but can also hydrolyze other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their c...
Gene Name:
ENPP1
Uniprot ID:
P22413
Molecular Weight:
104923.58 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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
Kind
Protein
Organism
DENV-2
Pharmacological action
unknown
General Function:
Structural molecule activity
Specific Function:
Capsid protein 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 virion assembly by masking and inactivating envelope protein E fusion peptide. prM is matured in the last step of virion assembly, presumably to avoid catastrophic activation of the viral fusion peptide...
Gene Name:
Not Available
Uniprot ID:
P12823
Molecular Weight:
379216.195 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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Poly(a) rna binding
Specific Function:
ATP dependent phosphorylation of adenosine and other related nucleoside analogs to monophosphate derivatives. Serves as a potential regulator of concentrations of extracellular adenosine and intracellular adenine nucleotides.
Gene Name:
ADK
Uniprot ID:
P55263
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. [PubMed:15917509 ]

Transporters

Kind
Protein
Organism
Human
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) and is sodium-independent. It has a higher affinity for adenosine. Inhibited by dipyridamole and dilazep (anticancer chemotherapeutics drugs).
Gene Name:
SLC29A1
Uniprot ID:
Q99808
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. [PubMed:20096989 ]
  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. [PubMed:20185188 ]
Kind
Protein
Organism
Human
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 subtype (N3/cib) (with marked transport of both thymidine and inosine). Employs a 2:1 sodium/nucleoside ratio. Also able to transport gemcitabine, 3'-azido-3'-deoxythymidine (AZT), ribavirin and 3-deazaurid...
Gene Name:
SLC28A3
Uniprot ID:
Q9HAS3
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. [PubMed:20096989 ]
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Drug created on June 13, 2005 07:24 / Updated on July 28, 2016 03:05