Issue 21, 2016

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

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

Supplementary files

Article information

Article type
Communication
Submitted
14 ربيع الثاني 1437
Accepted
30 ربيع الثاني 1437
First published
01 جمادى الأولى 1437

Chem. Commun., 2016,52, 4037-4040

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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