10327. Tarenflurbil

Nomenclature

CAS number: 51543-40-9
(αR)-2-Fluoro-α-methyl-[1,1′-biphenyl]-4-acetic acid; ()-2-(2-fluoro-4-biphenylyl)propionic acid; (R)-flurbiprofen; E-7869; MPC-7869; Flurizan (Myriad).
C15H13FO2; mol wt 244.26.
C 73.76%, H 5.36%, F 7.78%, O 13.10%.

Description and references

γ-Secretase inhibiting isomer of flurbiprofen, q.v. Lowers brain levels of the 42-residue isoform of amyloid β peptide (Aβ42) that is implicated in Alzheimer's disease pathology. Prepn of racemate: BE 658723; S. S. Adams et al., US 3755427 (1965, 1973 both to Boots); of isomers: J. S. Nicholson, J. L. Turner, US 4188491 (1980 to Boots); R. Hardy et al., US 5599969 (1997 to Boots). Determn in plasma using capillary electrophoresis: A. Rousseau et al., Electrophoresis 29, 3641 (2008) DOI PubMed. Effect on γ-secretase and Aβ42 in vivo: J. L. Eriksen et al., J. Clin. Invest. 112, 440 (2003) DOI PubMed. Clinical pharmacokinetics and safety: D. R. Galasko et al., Alzheimer Dis. Assoc. Disord. 21, 292 (2007) DOI PubMed. Evaluation in Alzheimer's disease patients: G. K. Wilcock et al., Lancet Neurol. 7, 483 (2008) DOI PubMed. Review of development and clinical experience: H. Geerts, IDrugs 10, 121-133 (2007) PubMed.

Chemical structure

Properties

Crystals from n-heptane. [α]D20 29.5°. Sol in methanol.

Therapeutic Category

Antiamyloidogenic agent; in treatment of Alzheimer's disease.

Keywords

Antiamyloidogenic