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Filibuvir

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Chemical compound

Pharmaceutical compound

Filibuvir
Clinical data

Other names	PF-00868554
Routes of administration	Oral
ATC code	none
Legal status
Legal status	Development terminated
Identifiers
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
CAS Number	877130-28-4
PubChemCID	54708673
ChemSpider	26286922
UNII	198J479Y2L
KEGG	D09616
ChEMBL	ChEMBL490672
PDB ligand	AG0 (PDBe,RCSB PDB)
CompTox Dashboard(EPA)	DTXSID601007768
Chemical and physical data
Formula	C₂₉H₃₇N₅O₃
Molar mass	503.647 g·mol⁻¹
3D model (JSmol)	Interactive image
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 asPF-00868554,PF-868554) was a non-nucleoside orally available^[1]NS5B inhibitor developed byPfizer for the treatment ofhepatitis 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 meanIC50 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]

Its investigation was discontinued in February 2013 due to strategic reasons.^[5]^[6]

References

[edit]

^"Pfizer Halts Development of Hepatitis C Drug Filibuvir: Report".FirstWorld Pharma. Doctor's Guide Publishing Limited. Retrieved5 December 2015.
^Shi ST, Herlihy KJ, Graham JP, Nonomiya J, Rahavendran SV, Skor H, et al. (June 2009)."Preclinical characterization of PF-00868554, a potent nonnucleoside inhibitor of the hepatitis C virus RNA-dependent RNA polymerase".Antimicrobial Agents and Chemotherapy.53 (6):2544–52.doi:10.1128/AAC.01599-08.PMC 2687230.PMID 19307358.
^Jiao P, Xue W, Shen Y, Jin N, Liu H (April 2014). "Understanding the drug resistance mechanism of hepatitis C virus NS5B to PF-00868554 due to mutations of the 423 site: a computational study".Molecular BioSystems.10 (4):767–77.doi:10.1039/c3mb70498j.PMID 24452008.
^Beaulieu PL (December 2010). "Filibuvir, a non-nucleoside NS5B polymerase inhibitor for the potential oral treatment of chronic HCV infection".IDrugs.13 (12):938–48.PMID 21154154.
^Loftus P (8 March 2013)."Pfizer Stops Developing Hepatitis C Drug".The Wall Street Journal. Dow Jones & Company, Inc. Retrieved5 December 2015.
^Gentile I, Buonomo AR, Zappulo E, Borgia G (February 2015). "Discontinued drugs in 2012 - 2013: hepatitis C virus infection".Expert Opinion on Investigational Drugs.24 (2):239–51.doi:10.1517/13543784.2015.982274.PMID 25384989.S2CID 39936873.

RNA virus antivirals (primarilyJ05, alsoS01AD andD06BB)

Hepatitis C

NS3/4A protease inhibitors (–previr)	Asunaprevir Boceprevir^‡ Ciluprevir^§ Danoprevir^† Faldaprevir^‡ Glecaprevir Grazoprevir Narlaprevir Paritaprevir Simeprevir Sovaprevir^† Telaprevir^‡ Vaniprevir Vedroprevir^§ Voxilaprevir
NS5A inhibitors (–asvir)	Coblopasvir Daclatasvir^# Elbasvir Ledipasvir Odalasvir^† Ombitasvir Pibrentasvir Ravidasvir^† Ruzasvir^† Samatasvir^† Velpatasvir
NS5B RNA polymerase inhibitors (–buvir)	Beclabuvir^† Bemnifosbuvir^† Dasabuvir^# Deleobuvir^§ Filibuvir^§ GS-6620^§ IDX-184^§ Setrobuvir^§ Sofosbuvir^# Tegobuvir^§ TMC-647055^§ Radalbuvir^† Uprifosbuvir^†
Combination drugs	Elbasvir/grazoprevir Glecaprevir/pibrentasvir Ledipasvir/sofosbuvir^# Ombitasvir/paritaprevir/ritonavir^# Sofosbuvir/daclatasvir Sofosbuvir/velpatasvir^# Sofosbuvir/velpatasvir/voxilaprevir

Hepatitis D

Bulevirtide

Picornavirus

viral entry:Pleconaril^†

Anti-influenza agents

neuraminidase inhibitors/release phase (Oseltamivir^#
Zanamivir
Peramivir,Laninamivir^†)

Multiple/general

Interferon	Interferon alfa 2b Peginterferon alfa-2a^# Peginterferon alfa-2b^#
3CL protease inhibitors (–trelvir)	Atilotrelvir Ensitrelvir^† Ibuzatrelvir Leritrelvir Lufotrelvir Nirmatrelvir^† (+ritonavir)^† Rupintrivir Simnotrelvir (+ritonavir^†)
RNA pol inhibitors	CMX521^§ Deuremidevir^† Favipiravir Galidesivir^† GS-441524^§ Remdesivir MK-608^§ Mericitabine^† Molnupiravir NITD008^§ Ribavirin^# Taribavirin^† Triazavirin Valopicitabine^†
Multiple/Unknown/Other	EICAR^§ Merimepodib^§ Moroxydine Presatovir^†

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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