Ribavirin (CED0001627)

Record Information
Version1.0
Creation Date2016-05-22 03:45:50 UTC
Update Date2026-08-24 13:37:05 UTC
Accession NumberCHEM016864
Identification
Common NameRibavirin
ClassSmall Molecule
Description
Ribavirin belongs to the triazole ribonucleosides and ribonucleotides, a class of nucleosides, nucleotides, and analogues within the organic compounds. It has the chemical formula C8H12N4O5 and an average molecular weight of 244.20 g/mol. This compound is utilized as a drug (PMC6950311) and an antiviral drug (PMC7161744). It acts as an antagonist/inhibitor of RNA-directed RNA polymerase L, RNA-directed RNA polymerase catalytic subunit (PB1), Inosine-5'-monophosphate dehydrogenase 1 (IMPDH1), and the genome polyprotein, among other recorded protein targets. Ribavirin is used in the treatment of Lassa fever (PMC7125859), inflammation (PMC1513604), and COVID-19 (PMC8451976). Additionally, it has demonstrated a therapeutic effect on breast cancer (PMC12644199) and COVID-19 (PMC7381292). The compound is found in or released from 17 recorded sources. These include healthcare, pharmaceuticals and veterinary products such as antibiotics and antivirals; food, food processing and cookware, specifically the preparation of malt; household cleaning and consumer products including pipe accessories, other smoking requisites, non electric simulated smoking devices, cigar cigarettes; and electrical and electronic equipment including magnets, line transmission systems, electrically stimulated smoking devices, antennas, and amplifiers. Recorded exposure routes for Ribavirin include oral, intravenous, respiratory, subcutaneous, and inhalation, with the latter supported by literature (PMC6259602).
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
1-beta-D-Ribofuranosyl-1,2,4-triazole-3-carboxamideChEBI
1-beta-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamideChEBI
RBVChEBI
RibavirinaChEBI
RibavirineChEBI
RibavirinumChEBI
CopegusKegg
RebetolKegg
RibasphereKegg
VirazoleKegg
1-b-D-Ribofuranosyl-1,2,4-triazole-3-carboxamideGenerator
1-Β-D-ribofuranosyl-1,2,4-triazole-3-carboxamideGenerator
1-b-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamideGenerator
1-Β-D-ribofuranosyl-1H-1,2,4-triazole-3-carboxamideGenerator
VilonaHMDB
ICN brand OF ribavirinHMDB
RibamideHMDB
RibamidylHMDB
Ribavirin merck brandHMDB
VirazideHMDB
Grossman brand OF ribavirinHMDB
Merck brand OF ribavirinHMDB
Pfizer brand OF ribavirinHMDB
RibovirinHMDB
Three rivers pharmaceuticals brand OF ribavirinHMDB
Dermatech brand OF ribavirinHMDB
Essex brand OF ribavirinHMDB
RibamidilHMDB
TribavirinHMDB
ViramideHMDB
Chemical FormulaC8H12N4O5
Average Molecular Mass244.205 g/mol
Monoisotopic Mass244.081 g/mol
CAS Registry Number36791-04-5
IUPAC Name1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide
Traditional Nameribavirin
SMILESNC(=O)C1=NN(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
InChI IdentifierInChI=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
InChI KeyIWUCXVSUMQZMFG-AFCXAGJDSA-N
Chemical Taxonomy
Description 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
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • 2-heteroaryl carboxamide
  • Monosaccharide
  • Azole
  • Tetrahydrofuran
  • Triazole
  • 1,2,4-triazole
  • Heteroaromatic compound
  • Carboxamide group
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility33.2 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity64.57 m³·mol⁻¹ChemAxon
Polarizability22.18 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-08nc-9320000000-385cc2e08cf140e0eceeNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0zpj-6922200000-75bb1d484addd27068eeNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-92e2bd11ded2c95f3fbdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-109ebb69f722bb3a92d7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-2900000000-c0d63d0633c304d466caNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03xr-5900000000-c6f13aea6e263f2557f4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-02t9-9500000000-cefa4afc53cf92b724c3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-9200000000-3a87882b304f3a9c9995Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-d5e98a470d0e674937d2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-c659efd26af31b3b98dcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-1900000000-56c00c62af197ae8eecbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-2900000000-aa387f940aedc4b69874Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-3900000000-795b88d3d651082dccb4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-02t9-9500000000-2ad23cf2e8f500d101ccNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014l-9000000000-6a9ceaf94e48a5856e63Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-18802a19d16454483630Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-9200000000-f26697f5224329016008Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-3900000000-03e82b27fd25878e95dcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-85ef00069e1dea09445aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-3900000000-ec554c2067df2f7a90a5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014l-9000000000-ab534ce4a5c6314c7208Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-1900000000-7ae21b4b727698a5723dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-bb8007898a445cd739f3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-2900000000-1adbeced61d49869fddeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-3900000000-578e72950c23b4569947Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03xr-5900000000-20580c55dac00f1cd88eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-2900000000-03d3603a440bbc568fa2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-925d29af1e6a96971b28Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-f9793e4464f513f01119Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-98d4200dc6471c3e92e6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dj-1960000000-8e1936b4490afdea1b45Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-3900000000-34acc3537097bf33c4ecNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ot-9400000000-9e7ebf6d4e248ffbf3bbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-2900000000-1aad1437a8d8217dea0eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-3900000000-0e379b4cf22b87e29955Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9100000000-0c0a02c5d745eb2131d7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0910000000-b92809b971bc8eb2e054Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ow-9500000000-73f19728a3d0fd29f2beNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-9100000000-76d3f9bd6138557685d9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-2290000000-1c9e2bece678ea43e06dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-9200000000-7a6992a844bc0c8f9da0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9200000000-0dfdc401ec288b71a2f2Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2424.0Log mg/kg[1400:4300]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
inflammationis_treatment_forNot AvailablePMC1513604
breast cancerhas_therapeutic_effect_onNot AvailablePMC12644199
COVID-19has_therapeutic_effect_onNot AvailablePMC7381292
COVID-19is_treatment_forNot AvailablePMC8451976
Lassa feveris_treatment_forNot AvailablePMC7125859
Exposure Sources
Source IDSourceSectorReference
233BrushesPersonal care & cosmeticsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
351AntiviralsHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
528MicrophonesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
591LifeboatsMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
602MolluscicidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Adenosine receptor A1 structureClick to view 3D structureAdenosine receptor A1P30542HumansPredicted (SEA)15.7255
Click to view 3D structureAdenosine receptor A1Q60612Mus musculusPredicted (SEA)6.61718
Click to view 3D structureAdenosine receptor A1P25099Rattus norvegicusPredicted (SEA)56.8299
Click to view 3D structureAdenosine deaminaseP56658Bos taurusPredicted (SEA)6.69503
Click to view 3D structureAdenosine receptor A2aP30543Rattus norvegicusPredicted (SEA)55.5065
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)60.8781
Click to view 3D structureCytidine deaminaseP56389Mus musculusPredicted (SEA)0.389246
Heat shock protein HSP 90-alpha structureClick to view 3D structureHeat shock protein HSP 90-alphaP07900HumansPredicted (SEA)27.7143
Endoplasmin structureClick to view 3D structureEndoplasminP14625HumansPredicted (SEA)22.5763
Adenosine kinase structureClick to view 3D structureAdenosine kinaseP55263HumansPredicted (SEA)9.03051
Cytidine deaminase structureClick to view 3D structureCytidine deaminaseP32320HumansPredicted (SEA)0.233548
Click to view 3D structureAdenosine receptor A3P28647Rattus norvegicusPredicted (SEA)35.6549
Click to view 3D structureAdenosine kinaseA5U4N0Mycobacterium tuberculosis (strain ATCC 25177 / H37Ra)Predicted (SEA)4.98235
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)72.2441
Solute carrier family 28 member 3 structureClick to view 3D structureSolute carrier family 28 member 3Q9HAS3HumansPredicted (SEA)1.63483
Click to view 3D structureAdenosine receptor A1P47745Cavia porcellusPredicted (SEA)25.1453
Eukaryotic translation initiation factor 4E structureClick to view 3D structureEukaryotic translation initiation factor 4EP06730HumansPredicted (SEA)0.622794
Click to view 3D structureAdenosine receptor A1P28190Bos taurusPredicted (SEA)37.9126
Adenosine receptor A2b structureClick to view 3D structureAdenosine receptor A2bP29275HumansPredicted (SEA)70.1422
Adenosine deaminase structureClick to view 3D structureAdenosine deaminaseP00813HumansPredicted (SEA)5.13805
Click to view 3D structureAdenosine kinaseP9WID5Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)15.492
High affinity choline transporter 1 structureClick to view 3D structureHigh affinity choline transporter 1Q9GZV3HumansPredicted (SEA)20.1629
Click to view 3D structureAdenosine receptor A1P49892Gallus gallusPredicted (SEA)21.0971
Click to view 3D structureAdenosine kinaseP9WID4Mycobacterium tuberculosis (strain CDC 1551 / Oshkosh)Predicted (SEA)5.3716
Click to view 3D structureAdenosine receptor A3Q61618Mus musculusPredicted (SEA)30.8283
Concentrations
Not Available
External Links
DrugBank IDDB00811
HMDB IDHMDB0014949
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRibavirin
Chemspider ID34439
ChEBI ID63580
PubChem Compound ID37542
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. 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.
3. 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.
4. 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.
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21827730
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22052088
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22052220
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22156853
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22158703
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22212566
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22212568
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22212569
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22212572
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22212576
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22212579
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22220723
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22239498
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=22239511
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=29438107