15(S)-Fluprostenol isopropyl ester

15(S)-Fluprostenol isopropyl ester (15(S)-Flu-Ipr) is the unnatural C-15 epimer of Travoprost. Travoprost is the Alcon trade name for fluprostenol isopropyl ester, (Flu-Ipr) an F-series prostaglandin analog which has been approved for use as an ocular hypotensive drug.{8839,9613} Flu-Ipr is a prodrug which is converted by esterase enzymatic activity in the cornea to yield the corresponding free acid. The free acid, fluprostenol, is a potent FP receptor agonist.{8322} In human and animal models of glaucoma, FP receptor agonist activity corresponds very closely with intraocular hypotensive activity. Although data is currently not available for the activity of 15(S)-Flu-Ipr, inversion of the stereochemistry at the 15 position of ocular hypotensive prostaglandins generally lowers the potency approximately 100 fold.{1107}