17-phenyl trinor Prostaglandin F2α diethyl amide

17-phenyl trinor Prostaglandin F_2α diethyl amide (17-phenyl trinor PGF_2α diethyl amide) is an analog of PGF_2α in which the C-1 carboxyl group has been modified to an N-diethyl amide. PG esters have been shown to have ocular hypotensive activity.¹ PG N-ethyl amides were recently introduced as alternative PG hypotensive prodrugs.² Studies have shown that bovine and human corneal tissue converts the N-ethyl amides of various PGs to the free acids with a conversion efficiency of about 2.5 μg/g corneal tissue/hr.³ However, dialkyl amides such as 17-phenyl trinor PGF_2α diethyl amide are inert to corneal amidase activity, and are not converted in any detectable amount to the corresponding free acids. These compounds may therefore be useful tools in elucidating the claim that PG amides have intrinsic intraocular hypotensive activity.

1. Bito, L.Z. Comparison of the ocular hypotensive efficacy of eicosanoids and related compounds Exp. Eye Res. 38,181-184(1984).
2. Woodward, D.F., Krauss, A.H., Chen, J., et al. The pharmacology of bimatoprost (Lumigan?) Surv. Ophthalmol. 45(Suppl 4),S337-S345(2001).
3. Maxey, K.M., Johnson, J., and LaBrecque, J. The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist Surv. Ophthalmol. 47(Suppl 1),S34-S40(2002).