13-TRANS LATANOPROST is a geometric isomer of the parent drug Latanoprost, characterized by a trans configuration at the 13-position of the cyclopentyl ring. This structural variation introduces distinct stereochemical properties, affecting its pharmacokinetic profile. The molecule retains key functional groups, including a 17-phenylpropanoic acid moiety, a 5-lipoxygenase-derived cyclopentyl ring, and a 13-hydroxy ester linkage. The trans double bond at C13-C14 disrupts conjugation compared to the cis parent compound, altering its conformational flexibility. This impurity arises during synthetic processes due to partial isomerization and serves as an HPLC reference standard for impurity profiling in Latanoprost formulations.
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InChI=1S/C26H38O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,16-17,19,21-25,27-29H,4,9,12-15,18H2,1-2H3/b8-3-,17-16+/t21-,22+,23+,24-,25+/m0/s1
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