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Sulfonate salts of the therapeutic agent dapsone: 4‐[(4‐aminophenyl)sulfonyl]anilinium benzenesulfonate monohydrate and 4‐[(4‐aminophenyl)sulfonyl]anilinium methanesulfonate monohydrate
Author(s) -
Gaytán-Barrientos Nancy Sarahy,
Morales-Morales David,
Herrera-Ruiz Dea,
Reyes-Martínez Reyna,
Rivera-Islas Jesús
Publication year - 2016
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229616003284
Subject(s) - sulfonyl , chemistry , hydrogen bond , sulfonate , salt (chemistry) , solubility , medicinal chemistry , molecule , aqueous solution , stereochemistry , organic chemistry , sodium , alkyl
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, C 12 H 13 N 2 O 2 S + ·C 6 H 5 O 3 S − ·H 2 O and C 12 H 13 N 2 O 2 S + ·CH 3 SO 3 − ·H 2 O, crystallize as hydrates and both compounds exhibit the same space group (monoclinic, P 2 1 / 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…O water and O water —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.