Characterization of beta-lapachone and methylated beta-cyclodextrin solid-state systems

AAPS PharmSciTech. 2007 Jul 27;8(3):E60. doi: 10.1208/pt0803060.

Abstract

The purpose of this research was to explore the utility of beta cyclodextrin (betaCD) and beta cyclodextrin derivatives (hydroxypropyl-beta-cyclodextrin [HPbetaCD], sulfobutylether-beta-CD [SBbetaCD], and a randomly methylated-beta-CD [RMbetaCD]) to form inclusion complexes with the antitumoral drug, beta-lapachone (betaLAP), in order to overcome the problem of its poor water solubility. RMbetaCD presented the highest efficiency for betaLAP solubilization and was selected to develop solid-state binary systems. Differential scanning calorimetry (DSC), X-ray powder diffractometry (XRPD), Fourier transform infrared (FTIR) and optical and scanning electron microscopy results suggest the formation of inclusion complexes by both freeze-drying and kneading techniques with a dramatic improvement in drug dissolution efficiency at 20-minute dissolution efficiency (DE(20-minute) 67.15% and 88.22%, respectively) against the drug (DE(20-minute) 27.11%) or the betaCD/drug physical mixture (DE(20-minute) 27.22%). However, the kneading method gives a highly crystalline material that together with the adequate drug dissolution profile make it the best procedure in obtaining inclusion complexes of RMbetaCD/betaLAP convenient for different applications of betaLAP.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2-Hydroxypropyl-beta-cyclodextrin
  • Calorimetry, Differential Scanning
  • Cyclodextrins / chemistry*
  • Microscopy, Electron, Scanning
  • Naphthoquinones / chemistry*
  • Solubility
  • Spectroscopy, Fourier Transform Infrared
  • X-Ray Diffraction
  • beta-Cyclodextrins / chemistry

Substances

  • Cyclodextrins
  • Naphthoquinones
  • beta-Cyclodextrins
  • 2-Hydroxypropyl-beta-cyclodextrin
  • beta-lapachone