Tafluprost (free acid)-d4 (Synonyms: AFP-172-d4)

Tafluprost (free acid)-d₄ contains four deuterium atoms at the 3', 3', 4', and 4' positions. It is intended for use as an internal standard for the quantification of tafluprost (free acid) by GC- or LC-mass spectrometry. A number of 17-phenyl trinor prostaglandin F_2α derivatives have been approved for the treatment of glaucoma.^1,2,3,4 Of these, the ones wherein the 13,14-double bond has been hydrogenated retain relatively good potency, but show a significantly reduced incidence of local irritant side effects.⁵ Alternatively, it was recently reported that analogs incorporating a 15-deoxy-15,15-difluoro modification also had a favorable ophthalmic activity profile.⁶

1.Woodward, D.F., Krauss, A.H.P., Chen, J., et al.The pharmacology of Bimatoprost (LumiganTM)Survey of Ophthalmology45S337-S345(2001) 2.Abramovitz, M., Adam, M., Boie, Y., et al.The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogsBiochim. Biophys. Acta1483(2)285-293(2000) 3.Sorbera, L.A., and CastaÑer, J.TravoprostDrugs Future25(1)41-45(2000) 4.Maxey, K.M., Johnson, J., Camras, C.B., et al.The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonistSuv. Ophthalmol.47(4)S34-S40(2002) 5.Resul, B., Stjernschantz, J., No, K., et al.Phenyl-substituted prostaglandins: Potent and selective antiglaucoma agentsJournal of Medicinal Chemistry36243-248(1993) 6.Takagi, Y., Nakajima, T., Shimazaki, A., et al.Pharmacological characteristics of AFP-168 (tafluprost), a new prostanoid FP receptor agonist, as an ocular hypotensive drugExperimental Eye Research78767-776(2004)