WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 206326
Description: Tarenflurbil, also known as (R)-Flurbiprofen, is an orally active synthetic enantiomer of flurbiprofen. Tarenflurbil activates c-Jun N terminal kinase, increases AP-1 binding to DNA, and downregulates cyclin D1 expression, resulting in arrest of tumor cells in the G1 phase of the cell cycle and apoptosis. This agent also affects the expression of nuclear factor kappa B, a rapid response transcription factor that stimulates the immune response to tumor cells. Tarenflurbil does not inhibit the enzyme cyclo-oxygenase. Tarenflurbil is currently tested in patients with mild Alzheimer's disease.
MedKoo Cat#: 206326
Chemical Formula: C15H13FO2
Exact Mass: 244.08996
Molecular Weight: 244.26
Elemental Analysis: C, 73.76; H, 5.36; F, 7.78; O, 13.10
Synonym: E7869, E 7869, E-7869, Flurizan, Furbiprofen, MPC-7869, MPC 7869, MPC7869, (R)-Flurbiprofen
IUPAC/Chemical Name: (R)-2-(3-Fluoro-4-phenylphenyl)propanoic acid
InChi Key: SYTBZMRGLBWNTM-SNVBAGLBSA-N
InChi Code: 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
SMILES Code: C[C@H](C1=CC=C(C2=CC=CC=C2)C(F)=C1)C(O)=O
Tarenflurbil, 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.
A Phase III clinical study evaluated 800 mg R-flurbiprofen twice-daily versus placebo for 18 months exclusively in 1800 patients with mild Alzheimer's disease. On June 30, 2008, the company announced to discontinued Flurizan due to the disappointed results. Prior to this termination, Myriad had sold distribution rights in the European Union to Lundbeck for an initial payment of $100 million, which Lundbeck has indicated it will now take as a write-down. See wikipedia.com
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