Plasticity in zwitterionic drugs: the bending properties of Pregabalin and Gabapentin and their hydrates

IUCrJ. 2019 May 22;6(Pt 4):630-634. doi: 10.1107/S2052252519004755. eCollection 2019 Jul 1.

Abstract

The investigation of mechanical properties in molecular crystals is emerging as a novel area of interest in crystal engineering. Indeed, good mechanical properties are required to manufacture pharmaceutical and technologically relevant substances into usable products. In such endeavour, bendable single crystals help to correlate microscopic structure to macroscopic properties for potential design. The hydrate forms of two anticonvulsant zwitterionic drugs, Pregabalin and Gabapentin, are two examples of crystalline materials that show macroscopic plasticity. The direct comparison of these structures with those of their anhydrous counterparts, which are brittle, suggests that the presence of water is critical for plasticity. In contrast, structural features such as molecular packing and anisotropic distribution of strong and weak interactions seem less important.

Keywords: hydrates; plastic bending; single-crystal transformations.

Grants and funding

This work was funded by Science Foundation Ireland grants 12/RC/2275 and 15/SIRG/3577.