Balapiravir

For research use only. Not for therapeutic Use.

  • CAT Number: I004595
  • CAS Number: 690270-29-2
  • Molecular Formula: C21H30N6O8
  • Molecular Weight: 494.5
  • Purity: 95%
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Balapiravir(CAT: I004595), also known as R-1626, is an antiviral drug that was developed for the treatment of hepatitis C virus (HCV) infection. It is a prodrug of a nucleoside analog that works by inhibiting the RNA-dependent RNA polymerase enzyme that is required for HCV replication. Balapiravir has been shown to be effective against several genotypes of HCV in preclinical studies and early clinical trials. However, later-stage clinical trials showed that it had limited efficacy and significant adverse effects, leading to its discontinuation as a potential treatment for HCV. Despite its failure in the treatment of HCV, balapiravir remains an important compound in the development of new antiviral drugs, as it helped to identify key targets and mechanisms for the development of effective treatments for viral infections.


Catalog Number I004595
CAS Number 690270-29-2
Synonyms

[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-azido-3,4-bis(2-methylpropanoyloxy)oxolan-2-yl]methyl 2-methylpropanoate; R-1626; Ro4588161; R1626;

Molecular Formula C21H30N6O8
Purity 95%
Target HCV Protease
Solubility DMSO: ≥ 100 mg/mL
Appearance Solid powder
Storage Store at -20°C
Overview of Clinical Research

Originator Novartis<br />
Developer Roche<br />
Class Antivirals; Pyrimidine nucleosides; Small molecules<br />
Mechanism of Action Hepatitis C virus NS 5 protein inhibitors<br />
Orphan Drug Status No<br />

IUPAC Name [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-azido-3,4-bis(2-methylpropanoyloxy)oxolan-2-yl]methyl 2-methylpropanoate
InChI InChI=1S/C21H30N6O8/c1-10(2)17(28)32-9-21(25-26-23)15(34-19(30)12(5)6)14(33-18(29)11(3)4)16(35-21)27-8-7-13(22)24-20(27)31/h7-8,10-12,14-16H,9H2,1-6H3,(H2,22,24,31)/t14-,15+,16-,21-/m1/s1
InChIKey VKXWOLCNTHXCLF-DXEZIKHYSA-N
SMILES CC(C)C(=O)OCC1(C(C(C(O1)N2C=CC(=NC2=O)N)OC(=O)C(C)C)OC(=O)C(C)C)N=[N+]=[N-]
Reference

1: Chen YL, Abdul Ghafar N, Karuna R, Fu Y, Lim SP, Schul W, Gu F, Herve M, Yokohama F, Wang G, Cerny D, Fink K, Blasco F, Shi PY. Activation of peripheral blood mononuclear cells by dengue virus infection depotentiates balapiravir. J Virol. 2014 Feb;88(3):1740-7. doi: 10.1128/JVI.02841-13. Epub 2013 Nov 20. PubMed PMID: 24257621; PubMed Central PMCID: PMC3911617.<br />
2: Nguyen NM, Tran CN, Phung LK, Duong KT, Huynh Hle A, Farrar J, Nguyen QT, Tran HT, Nguyen CV, Merson L, Hoang LT, Hibberd ML, Aw PP, Wilm A, Nagarajan N, Nguyen DT, Pham MP, Nguyen TT, Javanbakht H, Klumpp K, Hammond J, Petric R, Wolbers M, Nguyen CT, Simmons CP. A randomized, double-blind placebo controlled trial of balapiravir, a polymerase inhibitor, in adult dengue patients. J Infect Dis. 2013 May 1;207(9):1442-50. doi: 10.1093/infdis/jis470. Epub 2012 Jul 17. PubMed PMID: 22807519; PubMed Central PMCID: PMC3610419.<br />
3: Nelson DR, Zeuzem S, Andreone P, Ferenci P, Herring R, Jensen DM, Marcellin P, Pockros PJ, Rodr&iacute;guez-Torres M, Rossaro L, Rustgi VK, Sepe T, Sulkowski M, Thomason IR, Yoshida EM, Chan A, Hill G. Balapiravir plus peginterferon alfa-2a (40KD)/ribavirin in a randomized trial of hepatitis C genotype 1 patients. Ann Hepatol. 2012 Jan-Feb;11(1):15-31. PubMed PMID: 22166557; PubMed Central PMCID: PMC3739984.<br />
4: Li F, Wu X, Hadig X, Huang S, Hong L, Tran T, Brandl M, Alfredson T. Chemical stability of 4&#39;-azidocytidine and its prodrug balapiravir. Drug Dev Ind Pharm. 2010 Apr;36(4):413-20. doi: 10.3109/03639040903225075. PubMed PMID: 19778160.

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