17-phenyl trinor Prostaglandin F2α ethyl amide-d4 (Synonyms: Bimatoprost-d4, 15(S)-Bimatoprost-d4, 17-phenyl trinor PGF2α ethyl amide-d4)

17-phenyl trinor Prostaglandin F_2α ethyl amide (17-phenyl trinor PGF_2α ethyl amide) is sold under the Allergan trade name Bimatoprost and is an F-series PG analog which has been approved for use as an ocular hypotensive drug.¹ Investigations in our lab have shown that 17-phenyl trinor PGF_2α ethyl amide is converted by an amidase enzymatic activity in the bovine and human cornea to yield the corresponding free acid, with a conversion rate of about 40 µg/g corneal tissue/24 hours.² The free acid, 17-phenyl trinor PGF_2α, is a potent FP receptor agonist.^3,4 In human and animal models of glaucoma, FP receptor agonist activity corresponds very closely with intraocular hypotensive activity.

1.Woodward, D.F., Krauss, A.H.P., Chen, J., et al.The pharmacology of Bimatoprost (LumiganTM)Survey of Ophthalmology45S337-S345(2001) 2.Maxey, K.M., Johnson, J., Camras, C.B., et al.The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonistSuv. Ophthalmol.47(4)S34-S40(2002) 3.Balapure, A.K., Rexroad, C.E., Jr., Kawada, K., et al.Structural requirements for prostaglandin analog interaction with the ovine corpus luteum prostaglandin F2α receptorBiochem. Pharmacol.38(14)2375-2381(1989) 4.Lake, S., Gullberg, H., Wahlqvist, J., et al.Cloning of the rat and human prostaglandin F2α receptors and the expression of the rat prostaglandin F2α receptorFEBS Letters355317-325(1994)