Cocrystallization is a way of changing the physical properties of a material by incorporating another chemical compound, a coformer, into its crystal. Cocrystallization holds great significance in the design of new organic materials and in the modification of drug properties such as shelf life and solubility in the bloodstream. Sulfa drugs, which are known for their antibacterial, antifungal, anti-inflammatory, and diuretic properties, have been previously cocrystallized with carboxylic acids which are known for their hydrogen-bond donating abilities. Because only two of eleven sulfa drugs tested were able to consistently form cocrystals with carboxylic acids, we sought to find a more effective set of coformers. Here we take advantage of the hydrogen-bond donating ability of the sulfonamide hydrogen, selecting coformers that are good hydrogen-bond acceptors. In this study, 200 cocrystallization experiments were carried out using eleven sulfa drugs and nine different coformers in search of a compound that would cocrystallize with a wide range of sulfa drugs. Thirty-one new sulfa drug cocrystals were synthesized and characterized by pNMR and FTIR. TPPO (triphenylphosphine oxide), which cocrystallized with seven of the eleven drugs tested, was found to be the most effective coformer.

Investigation of potential coformers for synthesis of sulfa drug cocrystals

253rd National Meeting (2017)

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