MPC-7869

Tarenflurbil

Clinical data
ATC code	none
Legal status
Legal status	Withdrawn after Phase III
Identifiers
IUPAC name (R)-2-(3-Fluoro-4-phenylphenyl)propanoic acid
CAS Number	51543-40-9 N
PubChem CID	92337
IUPHAR/BPS	7340
ChemSpider	83361 N
UNII	501W00OOWA
PDB ligand	FLR (PDBe, RCSB PDB)
ECHA InfoCard	100.052.041
Chemical and physical data
Formula	C15H13FO2
Molar mass	244.26 g/mol
3D model (JSmol)	Interactive image
SMILES Fc2cc(ccc2c1ccccc1)[C@H](C(=O)O)C
InChI InChI=1S/C15H13FO2/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11/h2-10H,1H3,(H,17,18)/t10-/m1/s1 N Key:SYTBZMRGLBWNTM-SNVBAGLBSA-N N
NY (what is this?)

Tarenflurbil,Flurizan or R-flurbiprofen, is the single enantiomer of the racemate NSAID flurbiprofen. For several years, research and trials for the drug were conducted by Myriad Genetics, to investigate its potential as a treatment for Alzheimer's disease; that investigation concluded in June 2008 when the company announced it would discontinue development of the compound.

At proposed therapeutic concentrations, this molecule lacks anti-inflammatory activity, and does not inhibit either cyclooxygenase 1 (COX-1) or cyclooxygenase 2 (COX-2) enzymes. Only the S-enantiomers of arylpropionic acid NSAID can potently inhibit COX, whereas the R-enantiomers exert almost no COX activity. R-Flurbiprofen is inefficiently converted into S-flurbiprofen, with 1.5% of the R-enantiomer undergoing bioinversion to the S-form. Although this compound lacks activity against COX, studies have shown that this drug is a potent reducer of levels of beta amyloid, the main constituent of amyloid plaques in Alzheimer's disease, and therefore there was interest in this drug as a therapeutic agent.

In 2005, Myriad Genetics reported the results of its Phase II clinical trial of Flurizan; it was the largest ever Alzheimer's drug treatment trial using R-flurbiprofen. Patients were split into three treatment groups, receiving placebo, 400 or 800 mg R-flurbiprofen twice daily for a year. Result from this trial showed that the drug was well tolerated, and positive trends were observed with the 800 mg twice-daily dose in patients with mild Alzheimer's disease. A subgroup of patients that were diagnosed with mild disease, and had high plasma drug levels had significantly less decline in two primary behavioral outcomes (Activities of Daily Living scale (ADCS-ADL) and Global Function (CDR-SB)). Approximately 80 patients enrolled in the optional follow-on study showed continuing benefits with R-flurbiprofen, with increasing positive trends over this period for all primary outcomes after 24 months. On March 5, 2007 Myriad reported final results of the two-year trial, showing that 42% of those 80 patients showed improvement or no decline in one or more of the three primary endpoints of cognition, global function and activities of daily living, compared to a typical 10% of patients on placebo.