Reference : Application of molecular modeling to the study of cyproterone acetate stability in the p...
Scientific journals : Article
Human health sciences : Pharmacy, pharmacology & toxicology
http://hdl.handle.net/2268/20376
Application of molecular modeling to the study of cyproterone acetate stability in the presence of cyclodextrin derivatives
English
Henry de Hassonville, Sandrine [ > > ]
Dive, Georges mailto [Université de Liège - ULg > > Centre d'ingénierie des protéines >]
Evrard, Brigitte mailto [Université de Liège - ULg > Département de pharmacie > Pharmacie galénique >]
Barillaro, Valery [> > > >]
Bertholet, Pascal [> > > >]
Delattre, Luc mailto [Université de Liège - ULg > Département de pharmacie > Département de pharmacie >]
Piel, Géraldine mailto [Université de Liège - ULg > Département de pharmacie > Pharmacie galénique et magistrale >]
2004
Journal of Drug Delivery Science and Technology
Editions Sante
14
5, SEP-OCT
357-362
Yes
International
1157-1489
Paris
[en] cyclodextrins ; cyproterone acetate ; stability ; molecular modeling ; methylated-beta-cyclodextrin ; gamma-cyclodextrin
[en] The ability of cyclodextrins (CDs) to increase the solubility of cyproterone acetate (CPA) was previously shown by phase-solubility and NMR studies [1]. In the present work, the influence of various CDs on the stability of CPA was studied in pH 6 and pH 8 aqueous solutions at 25degreesC. Different CDs were tested: hydroxypropyl-beta-cyclodextrin (HPbetaCD), randomly methylated beta-cyclodextrin (RAMEB), hydroxypropyl-gamma-cyclodextrin (HPgammaCD) and gamma-cyclodextrin (gammaCD). At pH 6, the presence of these CDs reduces the degradation of CPA. Nevertheless, at pH 8, the gamma-CD derivatives are ineffective against the degradation of CPA, whereas the beta-CD derivatives (HPbetaCD and RAMEB) allow decreasing CPA hydrolysis. Molecular modeling was performed to theoretically calculate some of the most energetically favorable conformations for gamma-CD and RAMEB complexes with CPA. The position of the ester group in the CD caivity seems to be the most important factor influencing the hydrolysis of CPA. Other factors, such as the size of the cavity, the substitution of the CD hydroxyls and the stability constant also have a strong incidence on CPA stability.
Researchers ; Professionals
http://hdl.handle.net/2268/20376

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