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
References
1. Choi MK, Kim MH, Maeng HJ, Song IS. (2015)
Contribution of CNT1 and ENT1 to ribavirin uptake in human hepatocytes.
Arch Pharm Res, 38 (5): 904-13. [PMID:25011570]
2. Gordon CJ, Tchesnokov EP, Woolner E, Perry JK, Feng JY, Porter DP, Götte M. (2020)
Remdesivir is a direct-acting antiviral that inhibits RNA-dependent RNA polymerase from severe acute respiratory syndrome coronavirus 2 with high potency.
J Biol Chem, 295 (20): 6785-6797. [PMID:32284326]
3. Wang Y, Anirudhan V, Du R, Cui Q, Rong L. (2020)
RNA-dependent RNA polymerase of SARS-CoV-2 as a therapeutic target.
J Med Virol, [Epub ahead of print]. DOI: 10.1002/jmv.26264 [PMID:32633831]
4. Wittine K, Stipković Babić M, Makuc D, Plavec J, Kraljević Pavelić S, Sedić M, Pavelić K, Leyssen P, Neyts J, Balzarini J et al.. (2012)
Novel 1,2,4-triazole and imidazole derivatives of L-ascorbic and imino-ascorbic acid: synthesis, anti-HCV and antitumor activity evaluations.
Bioorg Med Chem, 20 (11): 3675-85. [PMID:22555152]
5. Zhu W, Chen CZ, Gorshkov K, Xu M, Lo DC, Zheng W. (2020)
RNA-Dependent RNA Polymerase as a Target for COVID-19 Drug Discovery.
SLAS Discov, 25 (10): 1141-1151. [PMID:32660307]