bimatoprost isopropyl ester

Bimatoprost isopropyl ester is an F-series prostaglandin analog, which has been approved as a hypotensive drug.

Bimatoprost is an F-series prostaglandin (PG) analog approved for use as an ocular hypotensive drug. Oxidation of the C-15 hydroxyl group and amide hydrolysis of Bimatoprost produces 15-keto-17-phenyl trinor PGF2α, a potential metabolite when administered to animals. 15-keto PG analogs can be minor impurities in commercial preparations of corresponding bulk drug compounds. Although much less potent than the parent compound, 15-keto PGs can still produce a small but measurable decrease (1 mm Hg) in intraocular pressure of normal cynomolgus monkeys at a dose of 1 μg eye. 15-keto Latanoprost (15-keto-17-phenyl-13,14-dihydro trinor PGF2α isopropyl ester) acts as a miotic in normal cat eyes, causing an 8 mm reduction in pupillary diameter at 5 μg eye. This is less potent compared to many other F-type PGs; for example, PGF2α induces similar miosis at less than 1 μg eye.

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.