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Does solute stereochemistry influence percutaneous penetration?

C M Heard1, K R Brain

  • 1Welsh School of Pharmacy, University of Wales College of Cardiff, United Kingdom.

Chirality
|January 1, 1995
PubMed
Summary
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Percutaneous penetration is limited by the stratum corneum. While ceramides show potential for chiral discrimination, studies found no statistically significant differences in stereoisomer permeation rates through human skin.

Area of Science:

  • Dermatology
  • Physical Chemistry
  • Pharmacokinetics

Background:

  • The stratum corneum acts as the primary barrier to percutaneous drug absorption.
  • Keratin and ceramides are key components of the stratum corneum, potentially influencing drug stereochemistry.
  • Previous studies suggested ceramide monolayers exhibit stereoselective interactions with drug diastereomers.

Purpose of the Study:

  • To investigate the potential for chiral discrimination in skin permeation.
  • To determine if stereochemistry affects drug diffusion rates across the stratum corneum.
  • To obtain evidence for intrinsic stereoselectivity in skin permeation.

Main Methods:

  • Investigated binding of propranolol enantiomers to solubilized epidermal keratin.
  • Examined interactions of ephedrine diastereomers with ceramide monolayers.

Related Experiment Videos

  • Measured in vitro permeation rates of ephedrine diastereomers through human skin.

    • Main Results:

    • Keratin binding showed no significant stereoselectivity for propranolol enantiomers.
    • Ceramide monolayers displayed dose-dependent stereoselective interactions with ephedrine diastereomers.
    • In vitro human skin permeation rates for ephedrine diastereomers were not statistically different.

    Conclusions:

    • While ceramide interactions suggest potential stereoselectivity, this was not observed in human skin permeation.
    • Factors like time averaging and high diffusant concentrations may obscure subtle stereospecific interactions.
    • Current evidence does not support intrinsic stereoselectivity in skin permeation.