Eduardo L. Gutiérrez, Matheus S. Souza, Luan F. Diniz, Javier Ellena,
Salt formation approach was taken to improve Mebendazole (MBZ) solubility. MBZ polymorph A was easily recrystallized as a 1:1 nitrate salt (MBZ N) in methanol. Single crystal X-ray diffraction data show that MBZ N crystallizes in the P1¯ space group. By strong intermolecular H-bonding interactions, MBZ is associated with a nitrate anion forming a supramolecular R22(8) synthon. Crystal packing is stabilized by these H-bonds, through which each nitrate connects two molecules of MBZ forming chains along the b axis. The vibrational behavior studied by micro FT-Raman and FT-IR spectroscopy is consistent with the crystal structure. Thermal analysis of the salt indicates that the compound is stable up to 150 °C, when an almost simultaneous elimination of HNO3 and CO2 occurs. MBZ N equilibrium solubility was evaluated in hydrochloric acid 0.1 M solution and compared with those of MBZ A and C. An improvement in a factor of 5 and 1.22 was found respectively.
https://doi.org/10.1016/j.molstruc.2018.02.060
@article{Guti_rrez_2018, doi = {10.1016/j.molstruc.2018.02.060}, url = {https://doi.org/10.1016%2Fj.molstruc.2018.02.060}, year = 2018, month = {jun}, publisher = {Elsevier {BV}}, volume = {1161}, pages = {113--121}, author = {Eduardo L. Guti{\'{e}}rrez and Matheus S. Souza and Luan F. Diniz and Javier Ellena}, title = {Synthesis, characterization and solubility of a new anthelmintic salt: Mebendazole nitrate}, journal = {Journal of Molecular Structure} }