Abstract
Salt formation has been a traditional and successful strategy in modulating the biopharmaceutical physicochemical properties of the active pharmaceutical compound (API). Herein, we have prepared four salts of Sertraline (Srt) with oxalic, fumaric, maleic and methanesulfonic acids to improve the thermal stability and solubility of the API. Anion-exchange reaction and solvent crystallizations have been undertaken to prepare salts of the Srt. These crystalline phases have been characterized by single-crystal and powder X-ray diffraction, Fourier transformed infrared spectroscopy, thermal analysis, and solubility measurements. From the single-crystal structures, we have observed that the carboxylate salts contain anion-water clusters that guide the formation of 1D-anion channels and structures that are then coupled to Srt+ cations. The mesylate salt (SrtH Mes), which is anhydrous, also has an alternating layered structure of cations and anions. SrtH Mes is the most thermally stable salt (m.p 194 ºC) and shows moderate solubility enhancements over the parent hydrochloride one, SrtH Cl. Given this profile, it represents an alternative for new drug formulation, storage, and API purification. In this study, we show the application of crystal structure assessments and their solid-state characterizations to guide and provide a selection of solid forms as candidates for drug development.
Published Version
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