17-phenyl trinor prostaglandin f2a

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 Prostaglandin F2αdimethyl amide is an isomer of 17-phenyl trinor prostaglandin F2αethyl amide . N/A

17-phenyl trinor Prostaglandin F2α (17-phenyl trinor PGF2α) is a metabolically stable analog of PGF2α and is a potent agonist for the FP receptor, binding with a relative potency of 756% compared to that of PGF2α. The ethyl amide of 17-phenyl trinor PGF2α bimatoprost has been approved for use as an ocular hypotensive drug. 17-phenyl trinor PGF2α methyl amide is an analog of bimatoprost. Its biological and toxicological properties have not been evaluated.

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.

17-phenyl trinor Prostaglandin F2α N-ethyl amide (17-phenyl trinor PGF2α) is an F-series prostaglandin analog which has been approved for use as an ocular hypotensive drug, sold under the Allergan trade name 17-phenyl trinor PGF2α ethyl amide. Investigations in our lab have shown that 17-phenyl trinor PGF2α ethyl amide is converted by an amidase enzymatic activity in the human cornea to yield the corresponding free acid, with a conversion rate of about 25 μg/cornea/24 hours. The free acid, 17-phenyl trinor PGF2α, is a potent FP receptor agonist. 15(R)-17-phenyl trinor PGF2α is the 15-epi, or unnatural" isomer of this active free acid metabolite. It has much diminished FP receptor-mediated activity

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.

N-Desethyl Bimatoprost (17-phenyl trinor PGF2α amide) is an F-series PG analog in which the C-1 carboxyl group has been modified to an unsubstituted amide. PG esters have been shown to have ocular hypotensive activity. PG N-ethyl amides were recently introduced as alternative PG hypotensive prodrugs. Although it has been claimed that PG amides are not converted to the free acids in vivo, studies have shown that bovine and human corneal tissue converts the amides of various PGs to the free acids with a conversion efficiency of about 10-20% relative to the hydrolysis of isopropyl esters. 17-phenyl trinor PGF2α amide would be expected to show the typical intraocular effects of latanoprost, but with the much slower hydrolysis pharmacokinetics of the PG N-amides.