prostaglandin f-2α isopropyl ester

PGF2α isopropyl ester is an ester prodrug of PGF2α with enhanced lipid solubility. Due to better membrane penetration, PGF2α isopropyl ester is more suitable than PGF2α or PGF2α tromethamine salt for topical application in studies on intraocular pressure. The ester functionality is readily hydrolyzed in vivo to release the active compound PGF2α. When administered topically to the eyes of cynomolgus monkeys, a 5 μg dose reduces intraocular pressure by 68% after the fourth day of treatment.

15(S)-15-methyl Prostaglandin F2α (15(S)-15-methyl PGF2α) has been shown to have potent uterine stimulant and abortifacient properties when administered intramuscularly to induce labor. 15(S)-15-methyl PGF2α isopropyl ester is a lipophilic analog of 15(S)-15-methyl PGF2α methyl ester, which may be hydrolyzed in vivo to the fully active free acid.

Prostaglandin F2α (PGF2α) drives luteolysis and smooth muscle contraction by activating the FP receptor. Stable, lipophilic analogs of PGF2α are used to modulate luteolysis and treat glaucoma. 16-phenoxy tetranor Prostaglandin F2α isopropyl ester (16-phenoxy tetranor PGF2α isopropyl ester) is a lipophilic analog of 16-phenoxy tetranor PGF2α. Isopropyl esters of PGs serve as prodrugs, as they are efficiently hydrolyzed in certain tissues to generate the bioactive free acid.

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.