Pharmaceutical cocrystals of an analgesic drug ethenzamide (ETZ) with various coformers, namely, gallic acid (GA), 2-nitrobenzoic acid (2NB), 3-nitrobenzoic acid (3NB), 2,4-dinitrobenzoic acid (DNB), and 3-toluic acid (3TA) were synthesized by the solvent evaporation method. All the cocrystals were characterized by various analytical techniques, and the crystal structures were determined by the single-crystal X-ray diffraction method (SCXRD). SCXRD analysis revealed that all the synthesized cocrystals were formed through a robust supramolecular acid-amide heterosynthon except the ethenzamide/gallic acid cocrystal, where molecules interacted through O−H•••O hydrogen bond involving −OH of gallic acid and oxygen of amide group of the ETZ molecule. The physicochemical properties such as stability, hygroscopicity, and solubility studies of the ETZ−GA cocrystal were evaluated. It was found that the ETZ−GA cocrystal has a higher solubility (2fold) than that of the pure ETZ drug molecule. Hygroscopic study of the ETZ−GA cocrystal revealed that synthesized cocrystal was non-hygroscopic at ∼75% RH conditions. The ETZ−GA cocrystal found to be stable for a time period of four months at ambient temperature.
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