Latanoprost ethyl amide

Latanoprost ethyl amide (Lat-NEt) is a latanoprost analog in which the C-1 carboxyl group has been modified to an N-ethyl amide. Prostaglandin esters have been shown to have ocular hypotensive activity. Prostaglandin N-ethyl amides were recently introduced as alternative prostaglandin ocular hypotensive prodrugs. Although it has been claimed that prostaglandin ethyl amides are not converted to the free acids in vivo, studies in our laboratories have shown that bovine and human corneal tissue converts the N-ethyl amides of various prostaglandins to the free acids with a conversion rate of about 2.5 µg/g corneal tissue/hr. Lat-NEt would be expected to show the typical intraocular effects of Latanoprost free acid, but with the much slower hydrolysis pharmacokinetics of the prostaglandin N-amides.