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HPLC method for determination of the enantiomeric purity of a new ω chain aldehyde synthon used in the synthesis of travoprost

Monika Kosińska ,  Marta Zezula ,  Anna Rosa ,  Joanna Zagrodzka ,  Iwona Dams ,  Michał Chodyński ,  Anita Pietraszek ,  Małgorzata Krupa 

Pharmaceutical Research Institute (IF), Rydygiera 8, Warszawa 01-793, Poland


A new optically pure synthon, precursor of the ω chain, was applied for synthesis of Travoprost (Fig.1), which is a topical medication used for controlling the progression of glaucoma or ocular hypertension, by reducing intraocular pressure. It is a prostaglandin analogue that works by increasing the outflow of aqueous fluid from the eyes. [1]


Fig 1. Travoprost, namely izopropyl (Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(R,E)-3-hydroxy-4-(3-trifluoromethylphenoxy)but-1-enyl]cyclopentyl}hept-5-enoate

Synthesis of the new ω chain  synthon consisted of seven optimized synthetic steps. Identity and  enantiomeric purity of the synthesized compounds were determined.

Determining the enantiomeric purity of chiral therapeutic agents is important in the development of active pharmaceutical ingredients (API).  Analytical method used for this purpose must ensure fast and effective separation of isomers. The common and widely applied method which meets these requirements is high performance liquid chromatography (HPLC).

The HPLC methods for determination of investigated compounds were developed. The individual compounds were separated using columns containing polysaccharide chiral stationary phase. The mobile phase consisted of hexane with addition of an alcohol (methanol, ethanol or  isopropanol). UV detection with detector  wavelength was  220 nm was applied to determine the investigated compounds. In course of extensive research it was proven, that the developed methods are selective and sensitive for all separated compounds. Elaborated method fulfills the criteria of European Pharmacopoeia for API analysis and can be used to control the synthesis process. [2][3]



[3] European Directorate for the Quality of Medicines & HealthCare, European Pharmacopoeia 7.0, Chapter: 2.2.46 Chromatographic separation techniques (2010)

Projekt współfinansowany przez Unię Europejską z Europejskiego Funduszu Rozwoju Regionalnego w ramach Programu Operacyjnego Innowacyjna Gospodarka

nr UDA-POIG.01.03.01-14-068/08-00 „Opracowanie innowacyjnych technologii leków oftalmicznych o szczególnym znaczeniu terapeutycznym i społecznym”


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Submitted: 2012-03-20 23:08
Revised:   2012-05-10 09:32