Co-crystals of the antiretroviral nevirapine: crystal structures, thermal analysis and dissolution behaviour

被引：45

作者：

Caira, Mino R. ^{[1
]}

Bourne, Susan A. ^{[1
]}

Samsodien, Halima ^{[1
]}

Engel, Emile ^{[1
]}

Liebenberg, Wilna ^{[2
]}

Stieger, Nicole ^{[2
]}

Aucamp, Marique ^{[2
]}

机构：

[1] Univ Cape Town, Dept Chem, Ctr Supramol Chem Res, ZA-7701 Rondebosch, South Africa

[2] North West Univ, Unit Drug Res & Dev, Fac Hlth Sci, Potchefstroom, South Africa

来源：

CRYSTENGCOMM | 2012年 / 14卷 / 07期

基金：

新加坡国家研究基金会;

关键词：

X-RAY; SOLUBILITY; COCRYSTALS; INCLUSION;

D O I：

10.1039/c2ce06507j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Synthesis and physicochemical characterization of co-crystals of the antiretroviral drug nevirapine (NV) with the pharmaceutically acceptable co-formers saccharin, rac-tartaric acid, maleic acid, glutaric acid and salicylic acid are reported for the first time. The respective stoichiometric NV : co-former ratios are 2 : 1, 1 : 1, 1 : 1, 1 : 1 and 2 : 1. In the 1 : 1 co-crystals, the predicted R-2(2)(8) NV(amide)carboxylic acid supramolecular synthon occurs, whereas in the 2 : 1 species, the co-former is H-bonded to a centrosymmetric NV dimer formed via the R-2(2)(8) amide-amide synthon. Thermal analysis of three co-crystals revealed the unusual phenomenon of precipitation of NV from the melt. Co-crystallization of NV with maleic acid led to the highest (similar to fivefold) increase in the aqueous solubility of the drug.

引用

页码：2541 / 2551

页数：11

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