A new solvate of epalerstat, a drug for diabetic neuropathy

• Published in: Acta crystallographica. Section E, Crystallographic communications Vol. 73; no. Pt 8; pp. 1264 - 1267
• Main Authors: Putra, Okky Dwichandra, Umeda, Daiki, Fukuzawa, Kaori, Gunji, Mihoko, Yonemochi, Etsuo
• Format: Journal Article
• Language: English
• Published: England International Union of Crystallography 01.08.2017
• Subjects: Research Communications; crystal structure; monosolvate; hydrogen bonding; acetone; epalerstat; isotypic
• ISSN: 2056-9890; 2056-9890
• DOI: 10.1107/S2056989017010751

Epalerstat {systematic name: (5 )-5-[(2 )-2-methyl-3-phenyl-prop-2-en-1-yl-idene]-4-oxo-2-sulfanyl-idene-1,3-thia-zolidine-3-acetic acid} crystallized as an acetone monosolvate, C H NO S ·C H O. In the epalerstat mol-ecule, the methyl-propyl-enediene moiety is inclined to the phenyl ring and the five-membered rhodamine ring by 21.4 (4) and 4.7 (4)°, respectively. In addition, the acetic acid moiety is found to be almost normal to the rhodamine ring, making a dihedral angle of 85.1 (2)°. In the crystal, a pair of O-H⋯O hydrogen bonds between the carb-oxy-lic acid groups of epalerstat mol-ecules form inversion dimers with an (8) loop. The dimers are linked by pairs of C-H⋯O hydrogen bonds, enclosing (20) loops, forming chains propagating along the [101] direction. In addition, the acetone mol-ecules are linked to the chain by a C-H⋯O hydrogen bond. Epalerstat acetone monosolvate was found to be isotypic with epalerstat tertra-hydro-furan solvate [Umeda (2017 ▸). . E , 941-944].