Influence of hydroxypropyl-beta-cyclodextrin on the transdermal permeation and skin accumulation of oxybenzone

Drug Dev Ind Pharm. 2002 Oct;28(9):1117-24. doi: 10.1081/ddc-120014578.

Abstract

The objective of the present study was to determine the effects of hydroxypropyl-beta-cyclodextrin (HPCD) concentration on the transdermal permeation and skin accumulation of a model ultraviolet (UV) absorber, oxybenzone. The concentration of oxybenzone was held constant at 2.67 mg/mL for all formulations, while the HPCD concentrations varied from 0 to 20% (w/w). Complexation of oxybenzone by HPCD was demonstrated by differential scanning calorimetry. A modified Franz cell apparatus was used in the transdermal experiments, with aliquots of the receptor fluid assayed for oxybenzone by high-performance liquid chromatography. From the permeation data, flux of the drug was calculated. Skins were removed from the diffusion cells at specified time points over a 24-hr period and the oxybenzone content in the skin determined. The aqueous solubility of oxybenzone increased linearly with increasing HPCD concentration, following a Higuchi AL-type complexation. The stability constant of the reaction was calculated from the phase-solubility diagram and found to be 2047 M-1. As the concentration of HPCD was increased from 0 to 10%, transdermal permeation and skin accumulation of oxybenzone increased. Maximum flux occurred at 10% HPCD, where sufficient cyclodextrin was added to completely solubilize all oxybenzone. When the concentration of HPCD was increased to 20%, both transdermal permeation and skin accumulation decreased. These data suggest the formation of a drug reservoir on the surface of the skin.

MeSH terms

  • 2-Hydroxypropyl-beta-cyclodextrin
  • Administration, Cutaneous
  • Animals
  • Benzophenones / administration & dosage
  • Benzophenones / chemistry
  • Benzophenones / pharmacokinetics*
  • Calorimetry, Differential Scanning
  • Cyclodextrins / chemistry
  • Cyclodextrins / pharmacology*
  • Dose-Response Relationship, Drug
  • Excipients / chemistry
  • Excipients / pharmacology*
  • In Vitro Techniques
  • Mice
  • Mice, Hairless
  • Permeability / drug effects
  • Skin / metabolism
  • Skin Absorption / drug effects*
  • Solubility
  • Solvents
  • Sunscreening Agents / administration & dosage
  • Sunscreening Agents / chemistry
  • Sunscreening Agents / pharmacokinetics*
  • Thermodynamics
  • Time Factors
  • Water
  • beta-Cyclodextrins*

Substances

  • Benzophenones
  • Cyclodextrins
  • Excipients
  • Solvents
  • Sunscreening Agents
  • beta-Cyclodextrins
  • Water
  • 2-Hydroxypropyl-beta-cyclodextrin
  • oxybenzone