Filibuvir

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Systematic (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
Clinical data
Legal status	Development terminated
Routes of administration	Oral
Identifiers
CAS Number	877130-28-4
ATC code	none
PubChem	CID: 54708673
ChemSpider	26286922
UNII	198J479Y2L Y
KEGG	D09616
ChEMBL	CHEMBL490672
Synonyms	PF-00868554
PDB ligand ID	AG0 (PDBe, RCSB PDB)
Chemical data
Formula	C29H37N5O3
Molecular mass	503.636 g/mol
SMILES CCC1=CC(=CC(=N1)CC)CC[C@@]2(CC(=C(C(=O)O2)CC3=NN4C(=CC(=NC4=N3)C)C)O)C5CCCC5
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 Key:SLVAPEZTBDBAPI-GDLZYMKVSA-N

Filibuvir (also known as PF-00868554, PF-868554) was a non-nucleoside orally available 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. Several filibuvir-resistant mutations have been identified, M423 being the most common that occurred after filibuvir monotherapy. It was intended to be taken twice-daily.

Its investigation was discontinued on February 2013 due to strategic reasons.