Experimental determination and computational analysis of solid-liquid phase equilibrium of nifedipine in twelve pure solvents

被引：18

作者：

Wang, Guangle ^{[1
,2
,3
]}

Wang, Gang ^{[2
]}

Gong, Junbo ^{[1
,2
,3
]}

Li, Wenlong ^{[1
,3
]}

Shang, Zeren ^{[1
,3
]}

Zhao, Shaolei ^{[1
,3
]}

Dong, Weibing ^{[2
]}

Wang, Yan ^{[1
,3
]}

机构：

[1] Tianjin Univ, Sch Chem Engn & Technol, State Key Lab Chem Engn, Tianjin 300072, Peoples R China

[2] Qinghai Nationalities Univ, Sch Chem & Chem Engn, Xining 810007, Peoples R China

[3] Coinnovat Ctr Chem & Chem Engn Tianjin, Tianjin 300072, Peoples R China

来源：

JOURNAL OF CHEMICAL THERMODYNAMICS | 2020年 / 150卷

基金：

中国国家自然科学基金;

关键词：

Solubility; Intermolecular interactions; Molecular dynamic simulation; COSMO-RS model; Nifedipine; THERMODYNAMIC ANALYSIS; BINARY SOLVENTS; MOLECULAR-INTERACTIONS; DOUBLE-BLIND; PLUS WATER; 288.15; K; SOLUBILITY; CRYSTALLIZATION; MIXTURES; ACID;

D O I：

10.1016/j.jct.2020.106223

中图分类号：

O414.1 [热力学];

学科分类号：

摘要：

Nifedipine is an oral calcium channel blocker in clinical practice, and widely used to prevent and treat heart diseases. In this work, the equilibrium solubility of nifedipine (NIF) in twelve pure solvents including alcohols and esters was determined by static method at temperatures ranging from 283.15 K to 323.15 K. In all studied solvent systems, the solubility increases monotonously with increasing temperature. Besides, the effect of solvent properties on solid-liquid phase equilibrium of NIF was investigated. The results show that the solubility of NIF correlates well with the solvent properties in alcohol solvents but no obvious correlation can be found in ester solvents. In addition, the solubility data was correlated with the modified Apelblat equation, lambda h equation, van't Hoff equation and NRTL model, and the overall fitting ARD% are 0.94%, 2.15%, 2.75% and 4.03% respectively. Therefore, the modified Apelblat equation achieves the best fitting performance. Furthermore, in order to quantitatively study how the solute-solvent interaction affects the solubility, the solvation free energy was calculated by the molecular dynamic (MD) simulation. The absolute values of solvation free energy of esters (-18.96 to-20.32 kJ.mol(-1)) are higher than those of alcohols (-15.21 to-17.54 kJ.mol(-1)), which is consistent with the order of solubility values. Moreover, COSMO-RS sigma-profiles were employed to qualitatively describe the intermolecular interactions. Finally, the COSMO-RS model was employed to predict the solubility of NIF in the studied solvents. The results show a good performance on predicting the solubility of NIF though the deviations existed in some cases. (c) 2020 Elsevier Ltd.

引用

页数：13

共 61 条

[1] Solubility measurement, Hansen solubility parameters and solution thermodynamics of gemfibrozil in different pharmaceutically used solvents [J].

Abul Kalam, Mohd ;

Alshehri, Sultan ;

Alshamsan, Aws ;

Alkholief, Musaed ;

Ali, Raisuddin ;

Shakeel, Faiyaz .

DRUG DEVELOPMENT AND INDUSTRIAL PHARMACY, 2019, 45 (08) :1258-1264

[2] Solubility of a poorly soluble immunosuppressant in different pure solvents: Measurement, correlation, thermodynamics and molecular interactions [J].

Abul Kalam, Mohd ;

Khan, Abdul Arif ;

Alshamsan, Aws ;

Haque, Anzarul ;

Shakeel, Faiyaz .

JOURNAL OF MOLECULAR LIQUIDS, 2018, 249 :53-60

[3]

[Anonymous], 1996, SMALL WOOD HDB ORGAN

[4]

[Anonymous], 2012, MAT STUD 7 0

[5] Solubility, solution thermodynamics and molecular interactions of osimertinib in some pharmaceutically useful solvents [J].

Anwer, Md. Khalid ;

Mohammad, Muqtader ;

Fatima, Farhat ;

Alshahrani, Saad M. ;

Aldawsari, Mohammed F. ;

Alalaiwe, Ahmed ;

Al-Shdefat, Ramdan ;

Shakeel, Faiyaz .

JOURNAL OF MOLECULAR LIQUIDS, 2019, 284 :53-58

[6] Solubilities of L-aspartic, DL-aspartic, DL-glutamic, p-hydroxybenzoic, o-anistic, p-anisic, and itaconic acids in water from T = 278 K to T = 345 K [J].

Apelblat, A ;

Manzurola, E .

JOURNAL OF CHEMICAL THERMODYNAMICS, 1997, 29 (12) :1527-1533

[7] Morbidity and mortality in patients randomised to double-blind treatment with a long-acting calcium-channel blocker or diuretic in the International Nifedipine GITS study: Intervention as a Goal in Hypertension Treatment (INSIGHT) [J].

Brown, MJ ;

Palmer, CR ;

Castaigne, A ;

de Leeuw, PW ;

Mancia, G ;

Rosenthal, T ;

Ruilope, LM .

LANCET, 2000, 356 (9227) :366-372

[8]

Burger A., 1996, SCI PHARM, V64, P293

[9] Engineering of pharmaceutical materials: An industrial perspective [J].

Chow, Kwok ;

Tong, Henry H. Y. ;

Lum, Susan ;

Chow, Albert H. L. .

JOURNAL OF PHARMACEUTICAL SCIENCES, 2008, 97 (08) :2855-2877

[10] Prediction of ethenzamide solubility in organic solvents by explicit inclusions of intermolecular interactions within the framework of COSMO-RS-DARE [J].

Cysewski, Piotr .

JOURNAL OF MOLECULAR LIQUIDS, 2019, 290

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