Analytical profile of mono[{3-[4-(2-ethoxyethoxy)-benzoyloxy]-2-hydroxypropyl}-tert-butylammonium] fumarate

Authors: Ivan Malík ;  Lenka Mitterová ;  Fils Andriamainty ;  Petr Mokrý 1;  Miloš Lukáč 2;  Jozef Csöllei 1;  Jana Gališinová ;  Janka Karlovská 3
Authors‘ workplace: Katedra farmaceutickej chémie, Farmaceutická fakulta Univerzity Komenského ;  Ústav chemických léčiv, Farmaceutická fakulta, Veterinární a farmaceutická univerzita Brno 1;  Katedra chemickej teórie liečiv, Farmaceutická fakulta, Univerzita Komenského v Bratislave 2;  Laboratórium NMR, Farmaceutická fakulta, Univerzita Komenského v Bratislave 3
Published in: Čes. slov. Farm., 2012; 61, 44-52
Category: Original Articles


The present paper aims at a complex spectral and physicochemical evaluation of mono[{3-[4-(2-ethoxyethoxy)-benzoyloxy]-2-hydroxypropyl}-tert-butylammonium] fumarate, the potential ultra-short acting blocker of ß1-adrenergic receptors. The identity of the evaluated compound (labelled as UPB-2) was confirmed by 1H-, 13C-NMR and IR spectral data as well. The estimated physicochemical parameters included melting point data, solubility in various media, purity checking (adsorption thin-layer chromatography), surface activity determination (non--direct Traube stalagmometric method), acidobasic characteristics (pKa value determination by alkalimetric titration), log ε values estimation (spectrophotometrically in UV/VIS region) and a study of the influence of acidic and alkaline media towards the stability of UPB-2. Other experimentally estimated values were lipohydrophilic descriptors using RP-HPLC (log k’) and the log Pexps in various lipohydrophilic media by the shake flask method. Based on the log Pexp readouts, the ability to permeate across the brain-blood barrier was predicted. For the content determination of UBP-2 the RP-HPLC (reversed-phase HPLC), the method of an internal standard and UV/VIS spectrophotometry at the wavelength of 260 nm (aqueous medium) and at 258 nm (methanolic medium) was applied.

Key words:
ß1-blockers • analytical evaluation • spectral and physicochemical properties • content determination


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