Balapiravir

Balapiravir

Systematic (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
Clinical data
Legal status	Investigational New Drug
Identifiers
CAS Number	690270-29-2
PubChem	CID 11691726
ChemSpider	9866453
KEGG	D09582
ChEMBL	CHEMBL550936
Chemical data
Formula	C21H30N6O8
Molar mass	494.497
SMILES O=c1nc(N)ccn1C2OC(N=[N+]=[N-])(COC(=O)C(C)C)C(OC(=O)C(C)C)C2OC(=O)C(C)C
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 Key:VKXWOLCNTHXCLF-DXEZIKHYSA-N

Balapiravir (R-1626, Ro4588161) is an experimental antiviral drug which acts as a polymerase inhibitor. There were efforts to develop it as a potential treatment for hepatitis C, and it was subsequently also studied in Dengue fever, but was not found to be useful. Lower doses failed to produce measurable reductions in viral load, while higher doses produced serious side effects such as lymphopenia which precluded further development of the drug.^[1] Subsequent research found that excess cytokine production triggered by Dengue virus infection prevented the conversion of the balapiravir prodrug to its active form, thereby blocking the activity of the drug.^[2]

References

1. "A randomized, double-blind placebo controlled trial of balapiravir, a polymerase inhibitor, in adult dengue patients.". Ncbi.nlm.nih.gov. Retrieved 7 May 2014.
2. Chen Y, et al. Activation of Peripheral Blood Mononuclear Cells by Dengue Virus Infection Depotentiates Balapiravir. J. Virol. 2014; 88(3):1740-1747. doi: 10.1128/JVI.02841-13