Prodrugs pp 1281-1288 | Cite as

Case Study: Latanoprost: Isopropylester of a Prostaglandin F2α Analog

  • Paramita Bandyopadhyay
Part of the Biotechnology: Pharmaceutical Aspects book series (PHARMASP, volume V)


Latanoprost is an esterified prodrug and does not render its potent interaction with the prostaglandin F receptor until hydrolyzed to its free acid. The phenyl-substituted esters of PGF 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 PGF 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).


Aqueous Humor Prostaglandin Analogue Prostaglandin Leukot Essent Fatty Acid Ocular Hypotensive Agent Aqueous Humor Dynamics 


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© American Association of Pharmaceutical Scientists 2007

Authors and Affiliations

  • Paramita Bandyopadhyay
    • 1
  1. 1.Pfizer Global Research and DevelopmentKalamazoo

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