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Journal of Crystal Growth

Journal of Crystal Growth

IF: 1.7
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Manufacture and characterization of two distinct quasi-polymorphs of empagliflozin

Published:15 March 2020 DOI: 10.1016/j.jcrysgro.2020.125489
Paul Kim , Ga-Young Kim , Min-Yong Cho , Min-Jeong Lee , Guang J. Choi

Abstract

We investigated the polymorphic behaviors of empagliflozin (EMP), an SGLT2 inhibitor focusing on the preparation and characterization of its two distinct quasi-polymorphs combined with in-line monitoring of crystallization processes. EMP has only been reported as a single polymorph without pseudo-polymorphs so far. In this study, two differentiable crystal forms, the needle-shaped ‘Form I’ and platy-shaped ‘Form P’, were reproducibly created using an anti-solvent approach. Although the two forms of EMP yielded the same results in many of these analyses, they could be differentiated by powder X-ray diffraction (PXRD), differential scanning calorimetry (DSC), and microscopy. Based on a detailed analysis of DSC thermograms, a small but obvious transition was detected during the melting of crystalline EMP at 152–157?°C. This transition, which occurred at a low activation energy, was identified as a polymorphic transformation from Form P to Form I.

The anti-solvent crystallization process was monitored by in-line NIR absorbance measurements and interpreted using principal component analysis (PCA). The crystal form was dependent on the crystallization solvent. Two different solvent/anti-solvent pairs (ethanol-water and ethanol-hexane) yielded substantially different PCA results, indicating distinct pathways to the creation of each crystal form. Rapid nucleation and high crystal growth rate was achieved by crystallization under Scheme P, which also exhibited fluctuation in its PC score plot. This was associated with reversible polymorphic selection between the two crystal forms during the crystallization of EMP.

Substances (8)

Materials
Procduct Name CAS Molecular Formula Supplier Price
Empagliflozin 864070-44-0 C23H27ClO7 764 suppliers $5.00-$1950.00
Empagliflozin 864070-44-0 C23H27ClO7 764 suppliers $5.00-$1950.00
Empagliflozin 864070-44-0 C23H27ClO7 764 suppliers $5.00-$1950.00
Empagliflozin 864070-44-0 C23H27ClO7 764 suppliers $5.00-$1950.00
Empagliflozin 864070-44-0 C23H27ClO7 - Inquiry
Empagliflozin 864070-44-0 C23H27ClO7 - Inquiry
Empagliflozin 864070-44-0 - Inquiry
Empagliflozin 864070-44-0 - Inquiry

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