Physicochemical and crystal structure analysis of pranlukast pseudo-polymorphs II: Solvate and cocrystal

Hideaki Furuta; Shintaro Mori; Yasuo Yoshihashi; Etsuo Yonemochi; Hidehiro Uekusa; Kiyohiko Sugano; Katsuhide Terada

doi:10.1016/j.jpba.2015.03.008

Physicochemical and crystal structure analysis of pranlukast pseudo-polymorphs II: Solvate and cocrystal

J Pharm Biomed Anal. 2015:111:44-50. doi: 10.1016/j.jpba.2015.03.008. Epub 2015 Mar 17.

Authors

Hideaki Furuta¹, Shintaro Mori², Yasuo Yoshihashi¹, Etsuo Yonemochi³, Hidehiro Uekusa², Kiyohiko Sugano⁴, Katsuhide Terada¹

Affiliations

¹ Department of Pharmaceutics, Faculty of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan.
² Graduate School of Science and Engineering, Department of Chemistry and Materials Science, Tokyo Institute of Technology, 12-1-H62, Ookayama 2, Meguro-ku, Tokyo 152-8551, Japan.
³ School of Pharmacy and Pharmaceutical Sciences, Hoshi University, 2-4-41, Ebara, Shinagawa, Tokyo 142-8501, Japan.
⁴ Department of Pharmaceutics, Faculty of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan. Electronic address: kiyohiko.sugano@phar.toho-u.ac.jp.

PMID: 25854856
DOI: 10.1016/j.jpba.2015.03.008

Abstract

Pranlukast (PRS) is a leukotriene receptor antagonist for the treatment of bronchial asthma. In this study, six new solvates and one new cocrystal of PRS were characterized by PXRD, TG-DTA, DSC, vapor sorption analysis and the dissolution test. In addition, the crystal structures were determined by single crystal X-ray structure analysis. PRS was found to be a rare example of a promiscuous multicomponent crystal former. The crystal packing patterns of these crystals can be categorized into the sheet-like and channel-like patterns. The ethanol solvate (PRS/ethanol) and urea cocrystal (PRS/urea) were more stable than the others under humid conditions. PRS/ethanol showed an improved dissolution profile compared to PRS HH and PRS/urea.

Keywords: Crystal structure; Dissolution; Pranlukast; Pseudo-polymorph; Vapor sorption.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Chromones / chemistry*
Crystallization / methods
Ethanol / chemistry
Leukotriene Antagonists / chemistry*
Solubility
X-Ray Diffraction / methods

Substances

Chromones
Leukotriene Antagonists
Ethanol
pranlukast