Balapiravir

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]

Balapiravir

Legal status
Legal status	US: Investigational New Drug
Identifiers
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
CAS Number	690270-29-2 Y
PubChem CID	11691726
ChemSpider	9866453
UNII	VOT0LP7I9K
KEGG	D09582
ChEMBL	ChEMBL550936
CompTox Dashboard (EPA)	DTXSID40219098
Chemical and physical data
Formula	C21H30N6O8
Molar mass	494.505 g·mol−1
3D model (JSmol)	Interactive image
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