Studying of drug solubility in water and alcohols using drug-ammonium ionic liquid-compounds

Mohammad Halayqa , Aneta Pobudkowska-Mirecka , Urszula Domańska-Żelazna , Maciej Zawadzki

Abstract

Synthesis of three mefenamic acid (MEF) derivatives - ionic liquid compounds composed of MEF in an anionic form and ammonium cation (choline, MEF1), or {di(2-hydroxyethyl)dimethyl ammonium (MEF2)}, or {tri(2-hydroxyethyl)methyl ammonium compound (MEF3)} is presented. The basic thermal properties of pure compounds i.e. fusion temperatures, and the enthalpy of fusion of these compounds have been measured with differential scanning microcalorimetry technique (DSC). Molar volumes have been calculated with the Barton group contribution method. The solubilities of MEF1, MEF2 and MEF3 using the dynamic method were measured at constant pH in a range of temperature from (290 to 370) K in three solvents: water, ethanol and 1-octanol. The experimental solubility data have been correlated by means of three commonly known GE equations: the Wilson, NRTL and UNIQUAC with the assumption that the systems studied here present simple eutectic behaviour. The activity coefficients of pharmaceuticals at saturated solutions in each binary mixture were calculated from the experimental data. The formation of MEF-ionic liquid compounds greatly increases the solubility in water in comparison with pure MEF or complexes with 2-hydroxypropyl-β-cyclodextrin. The development of these compounds formulations will assist in medication taking into account oral solid or gel medicines.
Author Mohammad Halayqa ZChF
Mohammad Halayqa,,
- Department Of Physical Chemistry
, Aneta Pobudkowska-Mirecka ZChF
Aneta Pobudkowska-Mirecka,,
- Department Of Physical Chemistry
, Urszula Domańska-Żelazna
Urszula Domańska-Żelazna,,
-
, Maciej Zawadzki ZChF
Maciej Zawadzki,,
- Department Of Physical Chemistry
Journal seriesEuropean Journal of Pharmaceutical Sciences, ISSN 0928-0987
Issue year2018
Vol111
Pages270-277
Publication size in sheets0.5
Keywords in EnglishSynthesis MEF-IL-compoundsDSC dataExperimental solubilityMEF + water, ethanol, 1-octanolThermodynamic correlation
DOIDOI:10.1016/j.ejps.2017.09.052
URL http://www.sciencedirect.com/science/article/pii/S0928098717305444?via%3Dihub
Languageen angielski
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Score (nominal)35
ScoreMinisterial score = 35.0, 20-12-2017, ArticleFromJournal
Ministerial score (2013-2016) = 35.0, 20-12-2017, ArticleFromJournal
Publication indicators WoS Impact Factor: 2016 = 3.756 (2) - 2016=3.866 (5)
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