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
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Equilibrative nucleoside transporter 1 1
Sodium/nucleoside cotransporter 1 1
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
inosine monophosphate dehydrogenase 1 Primary target of this compound Hs Inhibitor Inhibition 5.6 – 6.0 pIC50 - 4
pIC50 5.6 – 6.0 (IC50 2.5x10-6 – 1x10-6 M) [4]
Description: In vitro inhibition of IMPDH (isoform not specified, human and mouse assayed)
inosine monophosphate dehydrogenase 2 Primary target of this compound Hs Inhibitor Inhibition 5.6 – 6.0 pIC50 - 4
pIC50 5.6 – 6.0 (IC50 2.5x10-6 – 1x10-6 M) [4]
Description: In vitro inhibition of IMPDH (isoform not specified, human and mouse assayed)
Targets where the ligand is described in the comment field
Target Comment