Physicochemical characterization of terbinafine-cyclodextrin complexes in solution and in the solid state View Full Text


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Article Info

DATE

2010-04

AUTHORS

Maite Uzqueda, Carmen Martín, Arantza Zornoza, Miguel Sánchez, Itziar Vélaz

ABSTRACT

Terbinafine (TB) is an allylamine derivative used as oral and topical antifungal agent. The physicochemical properties of the complexes between TB and different cyclodextrins (CDs): α-CD, β-CD, hydroxypropylβ-CD, methylβ-CD and γ-CD, have been studied in pH 12 aqueous solutions at 25 °C and in the solid state. Different phase solubility profiles of TB in the presence of CDs have been obtained: AL type for TB with hydroxypropylβ-CD and γ-CD, AP type for the complexes with methylβ-CD and α-CD, while a BS profile was found for TB-β-CD. The apparent stability constants of the complexes were calculated at 25 °C from the phase solubility diagrams. The higher increase of TB solubility, up to 200-fold, together with the higher value of the stability constant were found for the complex with methylβ-CD. Solid systems of 1:1 drug:CD molar ratio were prepared and characterised using X-ray diffraction patterns, thermal analysis and FTIR spectroscopy. The coevaporation method can be considered the best method in preparing these solid complexes. The complexes of TB with natural CDs, except with α-CD, were crystalline, whereas the methyl and hydroxypropyl derivatives gave rise to amorphous phases. Dissolution rate studies have been performed with TB-β-CD and TB-HPβ-CD complexes, showing a positive influence of complexation on the drug dissolution. More... »

PAGES

393-402

References to SciGraph publications

  • 2003-10. Influence of Cyclodextrin Complexation on the Physicochemical and Biopharmaceutical Properties of Ketoconazole in JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
  • 2002-12. The Aggregation of Cyclodextrins as Studied by Photon Correlation Spectroscopy in JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
  • 2004-05. Determination of crystalline content gradients in cold-drawn poly-L-lactic acid films by DSC in JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY
  • 2002-12. Recent Aspects of Pharmaceutical Application of Cyclodextrins in JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
  • 2002-08. Investigation on the Interaction of Bendazac with β-, Hydroxypropyl-β-, and γ-, yclodextrins in JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
  • 2006-05. Characterization of Complexes Between Naftifine and Cyclodextrins in Solution and in the Solid State in PHARMACEUTICAL RESEARCH
  • 2003-06. Improvement of the Physicochemical Properties of Clotrimazole by Cyclodextrin Complexation in JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
  • 1992-02. Terbinafine in DRUGS
  • 2002-12. Improvement in the Physicochemical Properties of Ketoconazole through Complexation with Cyclodextrin Derivatives in JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
  • 2005-11. Complexation of Ketoconazole by Native and Modified Cyclodextrins in JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
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    http://scigraph.springernature.com/pub.10.1007/s10847-009-9656-0

    DOI

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