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Open AccessArticle

Measurements, Thermodynamic Modeling, and a Hydrogen Bonding Study on the Solubilities of Metoprolol Succinate in Organic Solvents

by Jian Shen 1,*, Xianrui Liang 2 and Hao Lei 1
1
School of Materials and Chemical Engineering, Ningbo University of Technology, Ningbo 315016, China
2
College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, China
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(10), 2469; https://doi.org/10.3390/molecules23102469
Received: 2 September 2018 / Revised: 17 September 2018 / Accepted: 19 September 2018 / Published: 26 September 2018
(This article belongs to the Special Issue Intramolecular Hydrogen Bonding 2018)
The solubilities of metoprolol succinate (a cardioselective β1 adrenergic receptor) in methanol, ethanol, n-propanol, isopropanol, n-butanol, ethyl acetate, and acetone were measured at temperatures ranging from (278.2 to 318.2) K using a solid–liquid equilibrium method. The solubility of metoprolol succinate increases with increasing temperature. At a fixed temperature, the solubility decreases in the order methanol > ethanol > n-butanol > n-propanol > isopropanol > acetone > ethyl acetate. The enthalpy of fusion and the melting point of metoprolol succinate were determined by differential scanning calorimetry. The thermodynamic properties of the dissolution process, determined by a van’t Hoff analysis, have been obtained and are discussed. The modified Apelblat equation, Wilson model, and non-random two-liquid (NRTL) model were employed to correlate the solubilities of metoprolol succinate in different solvents. Finally, a quantitative structure–property relationship (QSPR) study of physical properties of solvents and density functional theory simulations of hydrogen-bonding structure were carried out to give the explanation for the sequence of solubility in alcohols. The density functional theory (DFT) calculations well illustrated that the solubility of metoprolol succinate in various alcohols can be mainly attributed to the intra- and intermolecular hydrogen bonds in metoprolol succinate-solvent complexes. View Full-Text
Keywords: metoprolol succinate; solubility; dissolution enthalpy; hydrogen bonding; thermodynamic model metoprolol succinate; solubility; dissolution enthalpy; hydrogen bonding; thermodynamic model
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Shen, J.; Liang, X.; Lei, H. Measurements, Thermodynamic Modeling, and a Hydrogen Bonding Study on the Solubilities of Metoprolol Succinate in Organic Solvents. Molecules 2018, 23, 2469.

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