(R)-6-Cyclopentyl-6-[2-(2,6-diethylpyridin-4-yl)ethyl]-3-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-5,6-dihydro-2H-pyran-2-one Chemical Properties

Density 

1.29

storage temp. 

room temp

solubility 

DMSO: soluble10mg/mL, clear

form 

powder

pka

4.50±1.00(Predicted)

color 

white to beige

InChIKey

SLVAPEZTBDBAPI-GDLZYMKVSA-N

Safety Information

WGK Germany 

3

Storage Class

11 - Combustible Solids

(R)-6-Cyclopentyl-6-[2-(2,6-diethylpyridin-4-yl)ethyl]-3-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-5,6-dihydro-2H-pyran-2-one Usage And Synthesis

Uses

Filibuvir is an orally active, selective non-nucleoside inhibitor of the HCV nonstructural 5B protein (NS5B) RNA-dependent RNA polymerase (RdRp). Filibuvir binds noncovalently in the thumb II allosteric pocket of NS5B. Filibuvir inhibits genotype 1a and 1b replicons with EC50s of 59 nM for both isoforms, respectively[1]. Filibuvir preferentially inhibits elongative RNA synthesis and potently decreases viral RNA accumulation[2].

Definition

ChEBI: Filibuvir is a member of triazolopyrimidines.

Biological Activity

Filibuvir is an orally available, potent and selective inhibitor of the hepatitis C virus (HCV) nonstructural 5B (NS5B) RNA-dependent RNA polymerase th at exhibits potent antiviral activity against subgenomic HCV replicons in cell culture assays. Also, Filibuvir potently inhibits viral replication in infected patients. Filibuvir interacts with the thumb site II of the viral polymerase.

References

[1] Wagner F, et al. Antiviral activity of the hepatitis C virus polymerase inhibitor filibuvir in genotype 1-infected patients. Hepatology. 2011 Jul;54(1):50-9. DOI:10.1002/hep.24342
[2] Guanghui Yi, et al. Biochemical study of the comparative inhibition of hepatitis C virus RNA polymerase by VX-222 and filibuvir. Antimicrob Agents Chemother. 2012 Feb;56(2):830-7. DOI:10.1128/AAC.05438-11