Filibuvir

Chemical compound From Wikipedia, the free encyclopedia

Filibuvir (also known as PF-00868554, PF-868554) was a non-nucleoside orally available[1] NS5B inhibitor developed by Pfizer 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.[2] Several filibuvir-resistant mutations have been identified, M423 being the most common that occurred after filibuvir monotherapy.[3] It was intended to be taken twice-daily.[4]

Other namesPF-00868554
Routes of
administrationOral
ATC code
  • none
Legal status
  • Development terminated
Quick facts Clinical data, Other names ...
Filibuvir
Clinical data
Other namesPF-00868554
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • Development terminated
Identifiers
  • (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
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC29H37N5O3
Molar mass503.647 g·mol−1
3D model (JSmol)
  • CCC1=CC(=CC(=N1)CC)CC[C@@]2(CC(=C(C(=O)O2)CC3=NN4C(=CC(=NC4=N3)C)C)O)C5CCCC5
  • 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
  • Key:SLVAPEZTBDBAPI-GDLZYMKVSA-N
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Its investigation was discontinued in February 2013 due to strategic reasons.[5][6]

References

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