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热力学在预测麻黄碱非对映异构体和对映异构体二元混合物溶解度中的应用

Thermodynamics in the prediction of the solubilities of binary mixtures of the diastereoisomers and enantiomers of ephedrine.

作者信息

Schmidt W F, Porter W, Carstensen J T

机构信息

College of Pharmacy, University of Georgia, Athens 30602.

出版信息

Pharm Res. 1988 Jun;5(6):391-5. doi: 10.1023/a:1015919913896.

DOI:10.1023/a:1015919913896
PMID:3244652
Abstract

Equations derived from the Clausius-Clapeyron and Prigogine-Defay equations were used to determine the free energy of mixing for diastereoisomers and enantiomers from heats of fusion and transition temperature data. These equations are applied to the thermodynamics of mixing of the six binary equimolar combinations of (1R,2S)-ephedrine, (1S,2R)-ephedrine; and (1R,2R)- and (1S,2S)-pseudoephedrine isomers. The relative equilibrium solubility of the binary mixtures in water is consistent with thermodynamic calculations.

摘要

从克劳修斯 - 克拉佩龙方程和普里戈金 - 德法伊方程推导出来的公式,被用于根据熔化热和转变温度数据来确定非对映异构体和对映异构体的混合自由能。这些公式被应用于(1R,2S)-麻黄碱、(1S,2R)-麻黄碱以及(1R,2R)-和(1S,2S)-伪麻黄碱异构体的六种二元等摩尔组合的混合热力学。二元混合物在水中的相对平衡溶解度与热力学计算结果一致。

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引用本文的文献

1
Nuclear magnetic resonance (NMR) spectroscopic investigation of interaction energies of ephedrine stereoisomers in noncrystalline solids and its correlation with thermodynamic data.非晶态固体中麻黄碱立体异构体相互作用能的核磁共振(NMR)光谱研究及其与热力学数据的相关性。
Pharm Res. 1991 Sep;8(9):1128-36. doi: 10.1023/a:1015898217143.
2
Formation of the racemic compound of ephedrine base from a physical mixture of its enantiomers in the solid, liquid, solution, or vapor state.在固体、液体、溶液或蒸汽状态下,其对映体的物理混合物形成麻黄碱碱的外消旋化合物。
Pharm Res. 1992 Aug;9(8):1083-91. doi: 10.1023/a:1015870915132.

本文引用的文献

1
Extended solubility approach: solubility parameters for crystalline solid compounds.扩展溶解度方法:结晶固体化合物的溶解度参数
J Pharm Sci. 1981 Feb;70(2):170-2. doi: 10.1002/jps.2600700214.
2
Expanded solubility parameter approach. I: Naphthalene and benzoic acid in individual solvents.扩展溶解度参数法。I:萘和苯甲酸在单一溶剂中的情况。
J Pharm Sci. 1984 Feb;73(2):179-88. doi: 10.1002/jps.2600730210.
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Stereochemical studies on medicinal agents. IV. Conformational analysis of ephedrine isomers and related compounds.
J Med Chem. 1967 Nov;10(6):1057-63. doi: 10.1021/jm00318a015.
4
Steric aspects of adrenergic drugs. II. Effects of DL isomers and desoxy derivatives on the reserpine-pretreated vas deferens.肾上腺素能药物的空间因素。II. DL异构体和脱氧衍生物对利血平预处理的输精管的影响。
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Molecular geometry and adrenergic drug activity.分子几何学与肾上腺素能药物活性。
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6
Solubility properties in polymers and biological media 5: an analysis of the physicochemical properties which influence octanol-water partition coefficients of aliphatic and aromatic solutes.聚合物和生物介质中的溶解性特性5:对影响脂肪族和芳香族溶质正辛醇-水分配系数的物理化学性质的分析
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Theoretical derivation of solute-solvent interaction parameter in binary solution: case of the deviation from Raoult's law.二元溶液中溶质-溶剂相互作用参数的理论推导:偏离拉乌尔定律的情况。
J Pharm Sci. 1986 May;75(5):463-8. doi: 10.1002/jps.2600750509.
8
Linear solvation energy relationships: 36. Molecular properties governing solubilities of organic nonelectrolytes in water.线性溶剂化能关系:36. 决定有机非电解质在水中溶解度的分子性质。
J Pharm Sci. 1986 Apr;75(4):338-49. doi: 10.1002/jps.2600750405.
9
Cosolvency and cosolvent polarity.共溶性与共溶剂极性。
Pharm Res. 1987 Jun;4(3):220-30. doi: 10.1023/a:1016456127893.