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

• Seven new solvates and one new cocrystal of pranlukast (PRS) were discovered.
• The PRS crystal structures were categorized into the sheet-like and channel-like patterns.
• PRS ethanolate showed an improved dissolution profile compared to PRS hemihydrate.

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.

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