TY - CONF A1 - Castro, R. A. E. A1 - Cortesao, A. M. A1 - Maria, T. M. R. A1 - Silva, M. R. A1 - Emmerling, Franziska A1 - Canotilho, J. A1 - Eusebio, M. E. S. T1 - New cocrystals of bexarotene with pyridinecarboxamide isomers sustained by the acid∙∙∙aromatic nitrogen supramolecular heterosynthon N2 - Pharmaceutical cocrystals are homogenous crystalline structures made up of two or more components in a definite stoichiometric ratio, where at least one of the components in the crystal lattice is an active pharmaceutical ingredient (API).1 Pharmaceutical cocrystals have opened the opportunity for engineering solid-state forms designed to have tailored properties to enhance drug product bioavailability and stability, as well a enhance processability of the solid material inputs in drug product manufacture. In this work the cocrystallization of bexarotene, an approved API by the U.S. Food and Drug Administration that belongs to Biopharmaceutics Classification System Class II (low solubility–high permeability), with pyridine carboxamide isomers (picolinamide, nicotinamide and isonicotinamide) was successfully undertaken. The synthesis was achieved by liquid assisted grinding (LAG) and the solids obtained were characterized by differential scanning calorimetry (DSC), infrared spectroscopy (FTIR-ATR), powder X-ray diffraction (XRPD), single crystal X-ray diffraction (SXD), and polarized light thermomicroscopy (PLTM). For bexarotene: picolinamide and bexarotene:isonicotinamide, 1:1 cocrystals were obtained directly from milling. SXD data of bexarotene:isonicotinamide cocrystal reveal acid∙∙∙aromatic nitrogen supramolecular heterosynthon and that the homosynthon amide∙∙∙amide in isonicotinamide is preserved. The bexarotene:nicotinamide mixtures prepared by ball milling give rise to simple binary solid–liquid phase diagram with an eutectic point, well described by the Schröder-van Laar equation. Melt crystallization of the 1:1 mixture gives rise to a cocrystal for which a complex phase behaviour is observed. T2 - 6th Meeting IAPC CY - Zagreb, Croatia DA - 04.09.2017 KW - Crystalline structure KW - Bexarotene KW - Powder X-ray diffraction KW - Single crystal X-ray diffraction KW - Infrared spectroscopy PY - 2017 AN - OPUS4-41063 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER -