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
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
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H30N6O8
Molar mass494.497 g·mol−1
3D model (JSmol)
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

References
  1. 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 (2013). "A randomized, double-blind placebo controlled trial of balapiravir, a polymerase inhibitor, in adult dengue patients". J Infect Dis. 207 (9): 1442–50. doi:10.1093/infdis/jis470. PMC 3610419. PMID 22807519.
  2. Chen Y, et al. (2014). "Activation of Peripheral Blood Mononuclear Cells by Dengue Virus Infection Depotentiates Balapiravir". J. Virol. 88 (3): 1740–1747. doi:10.1128/JVI.02841-13. PMC 3911617. PMID 24257621.


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