Synthesis, characterization and solubility of a new anthelmintic salt: Mebendazole nitrate

Autor(es)

Gutierrez, Eduardo L. ^{[1, 2, 3]} ; Souza, Matheus S. ^[1] ; Diniz, Luan F. ^[1] ; Ellena, Javier ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Inst Fis Sao Carlos, CP 369, BR-13560970 Sao Carlos, SP - Brazil

^[2] Consejo Nacl Invest Cient & Tecn, INQUISAL, San Luis - Argentina

^[3] Univ Nacl San Luis, Fac Quim Bioquim & Farm, Area Quim Fis, RA-5700 San Luis - Argentina

• Tipo de documento: Artigo Científico
• Fonte: Journal of Molecular Structure; v. 1161, p. 113-121, JUN 5 2018.
• Citações Web of Science: 0

Resumo

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 PT space group. By strong intermolecular H-bonding interactions, MBZ is associated with a nitrate anion forming a supramolecular R-2(2)(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 degrees 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. (C) 2018 Elsevier B.V. All rights reserved. (AU)

• Processo FAPESP: 15/25694-0 - Obtenção, caracterização e avaliação de novas formas sólidas cristalinas de fármacos usados no tratamento da tuberculose
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• Modalidade de apoio: Bolsas no Brasil - Mestrado
• Processo FAPESP: 13/03487-8 - Centro de caracterização de novas espécies minerais: espectroscopia Raman, difração por raios X e nêutrons, e microssonda eletrônica
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