bimatoprost acid

Bimatoprost acid (17-phenyl trinor PGF2α) is a metabolically stable analog of PGF2α and has a potential antagonistic activity for the FP receptor. It has a relative potency of 756% compared to PGF2α for binding to the FP receptor on ovine luteal cells.

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.

Prostaglandin F2α (PGF2α) drives luteolysis and smooth muscle contraction by activating the FP receptor. Bimatoprost methyl ester is a lipophilic analog of 17-phenyl trinor PGF2α, a potent agonist for the FP receptor. 17-phenyl trinor PGF2α binds the FP receptor on ovine luteal cells with a relative potency of 756% compared to that of PGF2α. Esters of PGs serve as prodrugs, as they are efficiently hydrolyzed in certain tissues to generate the bioactive free acid.