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Solubilizing steroidal drugs by β-cyclodextrin derivatives.

Dennis H Schwarz1, Annegret Engelke1, Gerhard Wenz1

  • 1Organic Macromolecular Chemistry, Campus C4.2, Saarland University, 66123 Saarbrücken, Germany.

International Journal of Pharmaceutics
|July 27, 2017
PubMed
Summary

Beta-cyclodextrin derivatives significantly enhance the solubility of hydrophobic steroidal drugs. Anionic heptakis-6-sulfoethylsulfanyl-6-deoxy-β-cyclodextrin (HSES) showed the highest complexation efficiency for steroids.

Keywords:
Binding constantCorticosteroidsCyclodextrinsDrug deliveryGonadal steroidsHeptakis[6-O-(4-sulfobutyl)]-beta-cyclodextrin (PubChem CID: 71307542)Inclusion compoundsSolubilizationSteroidsbeta-Cyclodextrin (PubChem CID: 444041)hydroxypropyl-beta-Cyclodextrin (PubChem CID: 44134771)

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Area of Science:

  • Pharmaceutical Sciences
  • Supramolecular Chemistry

Background:

  • Steroidal drugs exhibit poor water solubility, limiting their administration and bioavailability.
  • Beta-cyclodextrin (β-CD) and its derivatives are known to improve the solubility of hydrophobic active pharmaceutical ingredients (APIs).

Purpose of the Study:

  • To systematically review solubility enhancements of various steroids using β-CD derivatives.
  • To investigate the role of cyclodextrin structure and substituents in steroid solubilization.

Main Methods:

  • Systematic review of literature on steroid-cyclodextrin complexation.
  • Analysis of factors influencing solubility enhancement, including steric fit and cyclodextrin substituents.
  • Characterization of binding interactions using ROESY NMR spectroscopy.

Main Results:

  • Anionic heptakis-6-sulfoethylsulfanyl-6-deoxy-β-cyclodextrin (HSES) achieved 60-90% complexation efficiency for most tested steroids.
  • Neutral β-CD thioethers, heptakis-6-methylsulfanyl-6-deoxy-2-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)]-β-CD (HTMT) and heptakis-6-thioglyceryl-6-deoxy-β-CD (HTG), exhibited gender selectivity for testosterone and estradiol, respectively.
  • Solubilization primarily involves complexation of the A/B and C/D rings of the steroid framework.

Conclusions:

  • β-CD derivatives are effective in enhancing steroid solubility and bioavailability.
  • HSES is a highly efficient solubilizing agent for a broad range of steroids.
  • Specific β-CD thioethers demonstrate selective binding for hormonal steroids, suggesting potential for targeted drug delivery.