ProstaglandinF2α (PGF2α) drives luteolysis and smooth muscle contraction by activating the FP receptor. Stable, lipophilic analogs of PGF2α are used to modulate luteolysis and treat glaucoma. 16-phenoxytetranorProstaglandinF2α (16-phenoxytetranor PGF2α) is a metabolically stable form of PGF2α containing a 16-phenoxy group at the ω-terminus. It binds to the FP receptor on ovine luteal cells with much greater affinity (440%) than PGF2α. 16-phenoxytetranor PGF2α methylester is a lipophilic analog of 16-phenoxytetranor PGF2α. Methylesters of PGs serve as prodrugs, as they are efficiently hydrolyzed in certain tissues to generate the bioactive free acid.