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Issue 21, 2016
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Color polymorphs of aldose reductase inhibitor epalrestat: configurational, conformational and synthon differences

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Abstract

We report five crystalline polymorphs and an amorphous phase of epalrestat together with configurational isomerism and color behavior: form I (deep red), form II (deep orange), form III (bright yellow), form IV (yellow), and form V (orange) are in the E,Z configuration of the drug, and a Z,Z isomer (bright yellow). Two pathways are identified for polymorph conversion: direct transformation of the E,Z isomer and another pathway via the Z,Z isomer to the E,Z polymorphs. From a pharmaceutical perspective, the stability of polymorphs was established under grinding, solvent slurry and thermal conditions: form I (thermodynamic) > form II > form V > form III > form IV (least stable).

Graphical abstract: Color polymorphs of aldose reductase inhibitor epalrestat: configurational, conformational and synthon differences

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Supplementary files

Article information


Submitted
24 Jan 2016
Accepted
09 Feb 2016
First published
10 Feb 2016

Chem. Commun., 2016,52, 4037-4040
Article type
Communication

Color polymorphs of aldose reductase inhibitor epalrestat: configurational, conformational and synthon differences

B. Swapna, K. Suresh and A. Nangia, Chem. Commun., 2016, 52, 4037
DOI: 10.1039/C6CC00697C

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