title: Mebendazole mesylate monohydrate: a new route to improve the solubility of mebendazole polymorphs.
abstract: Mebendazole mesylate monohydrate, a new stable salt of mebendazole (MBZ), has been synthesized and fully characterized. It was obtained from recrystallization of MBZ forms A, B, or C in diverse solvents with the addition of methyl sulfonic acid solution. The crystal packing is first organized as a two-dimensional array consisting of rows of alternating MBZ molecules linked to columns of mesylate ions by hydrogen bonds. The three-dimensional structure is further developed by classical intermolecular interactions involving water molecules. In addition, nonclassical contacts are also found. The vibrational behavior is consistent with the crystal structure, the most important functional groups showing shifts to lower or higher frequencies in relation to the MBZ polymorphs. Thermal analysis indicates that the compound is stable up to 50°C. Decomposition occurs in five steps. Solubility studies show that the title compound presents a significant higher performance than polymorph C. © 2013 Wiley Periodicals, Inc. and the American Pharmacists Association J Pharm Sci 102:3528-3538, 2013.
authors.affiliation: Physics Instituto of São Carlos, Universidade of São Paulo, CP 369, 13560-970, São Carlos, SP, Brazil.
authors.forename: Karina
authors.initials: K
authors.lastname: de Paula
authors.forename: Gerardo E
authors.initials: GE
authors.lastname: Camí
authors.forename: Elena V
authors.initials: EV
authors.lastname: Brusau
authors.forename: Griselda E
authors.initials: GE
authors.lastname: Narda
authors.forename: Javier
authors.initials: J
authors.lastname: Ellena
mesh_terms: D003460:Crystallization / Q000379:methods; D006860:Hydrogen Bonding; D008463:Mebendazole / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D012995:Solubility; D012996:Solutions / Q000737:chemistry; D012997:Solvents / Q000737:chemistry
chemical_list: D008698:Mesylates; D012996:Solutions; D012997:Solvents; C045880:methanesulfonic acid; D008463:Mebendazole
keywords: FTIR-Raman spectroscopy; crystal structure; dissolution; mebendazole mesylate; solid state; thermal stability