A number of 17-aryl trinor and 16-aryloxy tetranor prostaglandin F2α derivatives have been approved for the treatment of glaucoma.1,2,3 These "ring" prostaglandin (PG) analogs have improved efficacy over the PGs with an n-alkyl lower side chain. 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.4 17-trifluoromethylphenyl-13,14-dihydro trinor PGF1α (17-TFM-PGF1α) is a typical "ring" analog reminiscent of the trifluoromethyl-phenoxy ring of Travoprost. The a chain of 17-TFM-PGF1α is saturated, making this compound a formal member of the one-series PGs. Recent work has shown that in the "ring" series of analogs, this modification has little impact on FP receptor binding.5 As an ocular hypotensive agent, it is expected that 17-TFM-PGF1α would act very much like the free acid of latanoprost.
1.Woodward, D.F., Krauss, A.H.P., Chen, J., et al.The pharmacology of Bimatoprost (LumiganTM)Survey of Ophthalmology45S337-S345(2001)
2.Stjernschantz, J.W.From PGF2α-isopropyl ester to latanoprost: A review of the development of xalatan. The proper lectureInvestigative Ophthalmology & Visual Science42(6)1134-1145(2001)
3.Sorbera, L.A., and CastaÑer, J.TravoprostDrugs Future25(1)41-45(2000)
4.Resul, B., Stjernschantz, J., No, K., et al.Phenyl-substituted prostaglandins: Potent and selective antiglaucoma agentsJournal of Medicinal Chemistry36243-248(1993)
5.deLong, M.A., Amburgey, J., Taylor, C., et al.Synthesis and in vitro evaluation of human FP-receptor selective prostaglandin analoguesBioorganic & Medicinal Chemistry Letters101519-1522(2000)
