17 phenyl trinor prostaglandin f2α isopropyl ester

17-phenyl trinor PGF2α N-ethyl amide is an F-series prostaglandin analog approved as an ocular hypotensive drug, sold under the Allergan trade name Bimatoprost. The N-ethyl amide prostaglandin prodrugs are converted into the active free acid more slowly than analogous prostaglandin ester prodrugs like latanoprost. This product is the isopropyl ester of the free acid prostaglandin corresponding to Bimatoprost. The free acid, 17-phenyl trinor PGF2α, is a potent FP receptor agonist, and in human and animal glaucoma models, FP receptor agonist activity closely correlates with intraocular hypotensive activity. The 17-phenyl trinor PGF2α isopropyl ester derivative was examined for IOP-lowering activity during latanoprost's development and, at a dose of 3 μg/eye in monkeys, was the most potent analog, reducing IOP by 1.3 mm Hg more than latanoprost, though it was also significantly more irritating to the eye.

17-phenyl trinor prostaglandin F2α (17-phenyl trinor PGF2α) derivatives have been approved for the treatment of glaucoma, with unsubstituted or meta-substituted aromatic derivatives being the most potent FP receptor agonists. 17-trifluoromethylphenyl trinor PGF2α, which contains an aromatic ring reminiscent of the trifluoromethyl-phenoxy ring in travoprost ((+)-fluprostenol isopropyl ester), is expected to act similarly to the free acid form of travoprost as an ocular hypotensive agent. Additionally, 17-phenyl trinor PGF2α is a potent luteolytic and abortifacient with a potency equal to or greater than that of fluprostenol and cloprostenol.

A number of 17-phenyl trinor prostaglandin F2α(17-phenyl trinor PGF2α) derivatives have been approved for the treatment of glaucoma.1,2,3Of 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.417-trifluoromethylphenyl-13,14-dihydro trinor PGF2αbears an aromatic ring which is reminiscent of the trifluoromethyl-phenoxy ring of travoprost ((+)-fluprostenol isopropyl ester). As an ocular hypotensive agent, it would be expected that 17-trifluoromethylphenyl-13,14-dihydro trinor PGF2αwould act very much like the free acid of latanoprost.