Case Study: Latanoprost: Isopropylester of a Prostaglandin F2α Analog
Latanoprost is an esterified prodrug and does not render its potent interaction with the prostaglandin F2α receptor until hydrolyzed to its free acid. The phenyl-substituted esters of PGF2α analogs were also found not to be metabolized by 15-hydroxyprostaglandin dehydrogenase, which is found in various ocular tissues, allowing them to penetrate the cornea where they are hydrolyzed to the active free acid form by esterases (Basu et al., 1994). In addition, latanoprost is also thought to be less irritating than the PGF2α isopropyl free ester when applied topically to the eye (Astin et al., 1994). Naturally occurring prostaglandins may cause marked microcirculatory changes in the eye; however, structural analogs with increased affinity and selectivity for prostaglandin F2 receptors, such as latanoprost, have little or no such effect (Stjernschantz et al., 2000).
KeywordsAqueous Humor Prostaglandin Analogue Prostaglandin Leukot Essent Fatty Acid Ocular Hypotensive Agent Aqueous Humor Dynamics
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