ribavirin   Click here for help

GtoPdb Ligand ID: 6842

Abbreviated name: RBV
Synonyms: Copegus® | Rebetol® | ribofluranosyl carboxamide | Virazole®
Approved drug PDB Ligand
ribavirin is an approved drug (FDA (1985), EMA (1999))
Compound class: Synthetic organic
Comment: Inhibits inosine-5'-monophosphate dehydrogenase 1 and RNA and also inhibits hepatitis C virus RNA-dependent RNA polymerase (NS5B).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 4
Rotatable bonds 3
Topological polar surface area 143.72
Molecular weight 244.08
XLogP -2.43
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OCC1OC(C(C1O)O)n1cnc(n1)C(=O)N
Isomeric SMILES OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc(n1)C(=O)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
InChI Key IWUCXVSUMQZMFG-AFCXAGJDSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1985), EMA (1999))
WHO Essential Medicine WHO Essential Medicines List (EML) (22nd List, 2021). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide
International Nonproprietary Names Click here for help
INN number INN
3543 ribavirin
Synonyms Click here for help
Copegus® | Rebetol® | ribofluranosyl carboxamide | Virazole®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9680963
Reactome Reaction Reactome logo R-HSA-9678749, R-HSA-9680836
Other databases
CAS Registry No. 36791-04-5
ChEBI CHEBI:63580
ChEMBL Ligand CHEMBL1643
DrugBank Ligand DB00811
DrugCentral Ligand 2373
GtoPdb PubChem SID 178103448
PubChem CID 37542
RCSB PDB Ligand RBV
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UniChem Compound Search for chemical match using the InChIKey IWUCXVSUMQZMFG-AFCXAGJDSA-N
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Wikipedia Ribavirin

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Tocris
Ribavirin
Cat. No. 4501