An insight into dapsone co-crystals: sulfones as participants in supramolecular interactions

Eutectics and Salt of Dapsone With Hydroxybenzoic Acids: Binary Phase Diagrams, Characterization and Evaluation

“…Powder dissolution study was carried out by an RC-6 dissolution test analyzer, using the USP paddle method at a rotation speed of 100 rpm at 37 C. The known amount of the sample (1.5 g of raw drug or multicomponent solids) was added into the dissolution vessels containing 200 mL of physiological pH, including 0.1 mol/L HCL (pH ¼ 1.2), sodium acetate buffer (pH ¼ 4.5), potassium dihydrogen phosphate buffer (pH ¼ 6.8) after being sieved through 100-mesh sieves to minimize the size effect on dissolution results. At regular time intervals (2,5,10,15,20,30,45,60, 120, 240 min), 2 ml of the aliquots were withdrawn and filter through a 0.45 mm filter into the centrifuge tube and the certain amount of dissolution medium (continually heated at 37 C) was added to the dissolution vessels. A certain amount of the solution was withdrawn from centrifuge tube to chromatographic vial and diluted with chromatographic grade acetonitrile.…”

“…14 It was first studied as sulfonamide antibiotics for the treatment of malaria, tuberculosis and leprosy. 15 Further studies reveal the remarkable anti-inflammatory effects of DAP on the treatment of skin diseases, like psoriasis 16 and papulopustular rosaceaskin. 17 Moreover, it also displays an anticonvulsant and neuroprotective effect on status epilepticus (SE).…”

“…21 Lots of efforts were devoted to overcoming the solubility limitation such as the development of amorphous solid dispersants with PVP K30, 22 inclusion compound with bCD, 23,24 nanoliposomes (NLs), 25 gel, 17 nanoemulsions 26 and cocrystals. 15,27,28 But some of these strategies are practical limited or could not achieve the desired goal to increase the solubility. More explorations are needed to continually improve its physicochemical properties, specifically dissolution and solubility property.…”

Sulfonate salts of the therapeutic agent dapsone: 4-[(4-aminophenyl)sulfonyl]anilinium benzenesulfonate monohydrate and 4-[(4-aminophenyl)sulfonyl]anilinium methanesulfonate monohydrate

“…As is the case for many therapeutic agents, low aqueous solubility (0.85 mg ml À1 , 1% Tween 80) (Jiang et al, 2014) and high toxicity (methemoglobinemia at daily doses >100 mg) (Tingle et al, 1997) are the main problems associated with the use of dapsone. In a different line of research, cocrystals of dapsone have been prepared to understand not only its structural properties (Deng et al, 2012;Martins et al, 2013;Smith & Wermuth, 2012a,b) but also its solubility and dissolution rate (Jiang et al, 2014;He et al, 2015). However, these derivatizations show no significant therapeutic improvements.…”

“…However, these derivatizations show no significant therapeutic improvements. In a different line of research, cocrystals of dapsone have been prepared to understand not only its structural properties (Deng et al, 2012;Martins et al, 2013;Smith & Wermuth, 2012a,b) but also its solubility and dissolution rate (Jiang et al, 2014;He et al, 2015). Even though drug-salt formation is a common strategy, this has not been the case for dapsone and thus few salts have been described.…”