Binding affinities of mometasone furoate and related compounds including its metabolites for the glucocorticoid receptor of rat skin tissue

J Steroid Biochem Mol Biol. 1993 Feb;44(2):141-5. doi: 10.1016/0960-0760(93)90021-n.

Abstract

The binding affinities of mometasone furoate (MF), its metabolites and related compounds for the glucocorticoid receptor of rat epidermis and dermis were measured. MF and its main metabolite exhibited binding affinities higher than those of alclomethasone dipropionate (ADP) and betamethasone dipropionate (BDP), but equivalent to betamethasone 17-valerate (BMV). For compound I (metabolite of MF), ADP, BDP and BMV, the binding affinity was found to be higher in epidermis relative to dermis. This difference in the dermal/epidermal binding ratio may be a favorable sign leading to a possible reduction of dermal collagen atrophy, a known side effect of glucocorticoids. In structure-binding relationship studies, esterification of the 17-OH by furoylation and introduction of the 9 alpha-Cl caused a marked increase of the binding affinity, whereas the 6 beta-hydroxylation led to a pronounced decrease.

MeSH terms

  • Administration, Topical
  • Animals
  • Animals, Newborn
  • Anti-Inflammatory Agents / metabolism*
  • Glucocorticoids
  • Molecular Structure
  • Mometasone Furoate
  • Pregnadienediols / chemistry
  • Pregnadienediols / metabolism*
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Glucocorticoid / metabolism*
  • Skin / metabolism*

Substances

  • Anti-Inflammatory Agents
  • Glucocorticoids
  • Pregnadienediols
  • Receptors, Glucocorticoid
  • Mometasone Furoate