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Effect of cyclodextrins on the solubility and antimycotic activity of sertaconazole: Experimental and computational studies

Perdomo-Lopez, I., Rodriguez-Perez, A. I., Yzquierdo-Peiro, J.M., White, Alex William, Estrada, E. G., Villa, T. G. and Torres-Labandeira, J. J. 2002. Effect of cyclodextrins on the solubility and antimycotic activity of sertaconazole: Experimental and computational studies. Journal of Pharmaceutical Sciences 91 (11) , pp. 2408-2415. 10.1002/jps.10237

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This study investigated the effects of the complexation of sertaconazole nitrate with different cyclodextrin (CD) derivatives (α-CD, β-CD, γ-CD, hydroxypropyl-β-CD, and hydroxypropyl-γ-CD) on the aqueous solubility and antimycotic activity of the drug. Phase solubility studies indicated that the solubility of sertaconazole in enzyme-free simulated gastric- and enzyme-free simulated enteric fluids was significantly increased in the presence of cyclodextrins. The observed order of solubility increasing effect was: γ-CD > HPγ-CD > HPβ-CD > β-CD > α-CD. Solid-state sertaconazole–cyclodextrin complexes were prepared by freeze drying, and characterized by X-ray powder difractometry, differential scanning calorimetry (DSC), and infrared spectroscopy (FTIR). Freeze-dried complexes showed markedly higher solubility than both physical mixtures and sertaconazole alone. The antimycotic activities of sertaconazole–cyclodextrin complexes in solution were evaluated by inhibition zone assays with Candida albicans. The activity ranking agrees with the solubility ranking observed for these complexes, with the γ-CD–sertaconazole complex showing the strongest antimycotic activity. Finally, molecular modeling studies were carried out using the MM2 force field method, for complexes in vacuum and in water. This enable indentification of the preferred orientation of sertaconazole in the γ-CD cavity and of the main structural features responsible for the enhancement of its solubility and antimycotic activity. © 2002 Wiley-Liss, Inc. and the American Pharmaceutical Association J Pharm Sci 91:2408–2415, 2002

Item Type: Article
Status: Published
Schools: Pharmacy
Subjects: R Medicine > RS Pharmacy and materia medica
Publisher: WileyBlackwell
ISSN: 0022-3549
Last Modified: 04 Jun 2017 07:48

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