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

CrystEngComm Pub Date: 2011-12-23 DOI: 10.1039/C2CE06507J

Abstract

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 R22(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 R22(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 (～fivefold) increase in the aqueous solubility of the drug.

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