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Filibuvir

Filibuvir

  • CAT Number: I006602
  • CAS Number: 877130-28-4
  • Molecular Formula: C29H37N5O3
  • Molecular Weight: 503.647
  • Purity: ≥95%
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Filibuvir, also known as PF00868554, is a non-nucleoside orally available NS5B inhibitor under development for the treatment of hepatitis C. It binds to the non-catalytic Thumb II allosteric pocket of NS5B viral polymerase and causes a decrease in viral RNA synthesis. It is a potent and selective inhibitor, with a mean IC50 of 0.019 μM against genotype 1 polymerases. Its investigation was discontinued on February 2013 due to strategic reasons.

Catalog Number I006602
CAS Number 877130-28-4
Molecular Formula

C29H37N5O3

Purity 95%
Target NS5B inhibitor
Solubility Soluble in DMSO, not in water
Storage 0 - 4°C for short term or -20 °C for long term
IUPAC Name (2R)-2-cyclopentyl-2-[2-(2,6-diethylpyridin-4-yl)ethyl]-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-3H-pyran-6-one
InChI InChI=1S/C29H37N5O3/c1-5-22-14-20(15-23(6-2)31-22)11-12-29(21-9-7-8-10-21)17-25(35)24(27(36)37-29)16-26-32-28-30-18(3)13-19(4)34(28)33-26/h13-15,21,35H,5-12,16-17H2,1-4H3/t29-/m1/s1
InChIKey SLVAPEZTBDBAPI-GDLZYMKVSA-N
SMILES CCC1=CC(=CC(=N1)CC)CCC2(CC(=C(C(=O)O2)CC3=NN4C(=CC(=NC4=N3)C)C)O)C5CCCC5
Reference

</br>1:Computational study on the drug resistance mechanism of HCV NS5B RNA-dependent RNA polymerase mutants V494I, V494A, M426A, and M423T to Filibuvir. Wang H, Guo C, Chen BZ, Ji M.Antiviral Res. 2015 Jan;113:79-92. doi: 10.1016/j.antiviral.2014.11.005. Epub 2014 Nov 15. PMID: 25449363 </br>2:A phase 2 study of filibuvir in combination with pegylated IFN alfa and ribavirin for chronic HCV. Rodriguez-Torres M, Yoshida EM, Marcellin P, Srinivasan S, Purohit VS, Wang C, Hammond JL.Ann Hepatol. 2014 Jul-Aug;13(4):364-75. PMID: 24927607 Free Article</br>3:Determination and control of TEMPO, a potentially genotoxic free radical reagent used in the synthesis of filibuvir. Strohmeyer HE, Sluggett GW.J Pharm Biomed Anal. 2012 Mar 25;62:216-9. doi: 10.1016/j.jpba.2011.12.036. Epub 2012 Jan 8. PMID: 22269174 </br>4:Characterization of resistance to the nonnucleoside NS5B inhibitor filibuvir in hepatitis C virus-infected patients. Troke PJ, Lewis M, Simpson P, Gore K, Hammond J, Craig C, Westby M.Antimicrob Agents Chemother. 2012 Mar;56(3):1331-41. doi: 10.1128/AAC.05611-11. Epub 2011 Dec 27. PMID: 22203605 Free PMC Article</br>5:Biochemical study of the comparative inhibition of hepatitis C virus RNA polymerase by VX-222 and filibuvir. Yi G, Deval J, Fan B, Cai H, Soulard C, Ranjith-Kumar CT, Smith DB, Blatt L, Beigelman L, Kao CC.Antimicrob Agents Chemother. 2012 Feb;56(2):830-7. doi: 10.1128/AAC.05438-11. Epub 2011 Dec 5. PMID: 22143520 Free PMC Article</br>6:Antiviral activity of the hepatitis C virus polymerase inhibitor filibuvir in genotype 1-infected patients. Wagner F, Thompson R, Kantaridis C, Simpson P, Troke PJ, Jagannatha S, Neelakantan S, Purohit VS, Hammond JL.Hepatology. 2011 Jul;54(1):50-9. doi: 10.1002/hep.24342. PMID: 21488067 </br>7:Filibuvir, a non-nucleoside NS5B polymerase inhibitor for the potential oral treatment of chronic HCV infection. Beaulieu PL.IDrugs. 2010 Dec;13(12):938-48. Review. PMID: 21154154

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