title: Sulfonate salts of the therapeutic agent dapsone: 4-[(4-aminophenyl)sulfonyl]anilinium benzenesulfonate monohydrate and 4-[(4-aminophenyl)sulfonyl]anilinium methanesulfonate monohydrate.
abstract: Dapsone, formerly used to treat leprosy, now has wider therapeutic applications. As is the case for many therapeutic agents, low aqueous solubility and high toxicity are the main problems associated with its use. Derivatization of its amino groups has been widely explored but shows no significant therapeutic improvements. Cocrystals have been prepared to understand not only its structural properties, but also its solubility and dissolution rate. Few salts of dapsone have been described. The title salts, C12H13N2O2S(+)·C6H5O3S(-)·H2O and C12H13N2O2S(+)·CH3SO3(-)·H2O, crystallize as hydrates and both compounds exhibit the same space group (monoclinic, P21/n). The asymmetric unit of each salt consists of a 4-[(4-aminophenyl)sulfonyl]anilinium monocation, the corresponding sulfonate anion and a water molecule. The cation, anion and water molecule form hydrogen-bonded networks through N-H...O=S, N-H...Owater and Owater-H...O=S hydrogen bonds. For both salts, the water molecules interact with one sulfonate anion and two anilinium cations. The benzenesulfonate salt forms a two-dimensional network, while the hydrogen bonding within the methanesulfonate salt results in a three-dimensional network.
authors.affiliation: Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, C.P. 62209, Mexico.
authors.forename: Nancy Sarahy
authors.initials: NS
authors.lastname: Gaytán-Barrientos
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Coyoacán, 04510 México D.F., Mexico.
authors.forename: David
authors.initials: D
authors.lastname: Morales-Morales
authors.affiliation: Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, C.P. 62209, Mexico.
authors.forename: Dea
authors.initials: D
authors.lastname: Herrera-Ruiz
authors.affiliation: Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, C.P. 62209, Mexico.
authors.forename: Reyna
authors.initials: R
authors.lastname: Reyes-Martínez
authors.affiliation: Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, C.P. 62209, Mexico.
authors.forename: Jesús
authors.initials: J
authors.lastname: Rivera-Islas
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D001557:Benzenesulfonates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003622:Dapsone / Q000737:chemistry*; D006860:Hydrogen Bonding; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D012492:Salts
chemical_list: D000814:Aniline Compounds; D001557:Benzenesulfonates; D008698:Mesylates; D012492:Salts; C045880:methanesulfonic acid; D003622:Dapsone
keywords: anilinium; crystal structure; dapsone; hydrated salts; hydrogen bonding; solubility; therapeutic applications; toxicity