Permeation of WIN 55,212-2, a potent cannabinoid receptor agonist, across human tracheo-bronchial tissue in vitro and rat nasal epithelium in vivo

J Pharm Pharmacol. 2006 Nov;58(11):1459-65. doi: 10.1211/jpp.58.11.0006.

Abstract

The aim of this study was to investigate the intranasal absorption of R-(+)-WIN 55,212-2 mesylate in vivo and in vitro. Permeation experiments of R-(+)-WIN 55,212-2 formulations with 2% dimethyl-beta-cyclodextrin (DMbetaCD), 2% trimethyl-beta-cyclodextrin (TMbetaCD) or 2% randomly methylated-beta-cyclodextrin (RAMbetaCD) in 1:1 propylene glycol/saline and 1.5% propylene glycol +3% Tween 80 in saline were conducted using EpiAirway tissue and an anesthetized rat nasal absorption model, respectively. Samples were analysed by liquid chromatography-mass spectrometry. Mucosal tolerance was screened using paracellular marker permeation and tissue viability as indices. Nasal absorption of WIN 55,212-2 was rapid, with a t(max) (time of peak concentration) of 0.17 to 0.35 h in vivo. Relative to 1.5% propylene glycol +3% Tween 80 (control), 1:1 propylene glycol/saline, RAMbetaCD, DMbetaCD and TMbetaCD resulted in 24-, 20-, 17- and 10-fold WIN 55,212-2 permeation increases in vitro, respectively. The in vivo absolute bioavailabilities were also increased with 1:1 propylene glycol/saline, RAMbetaCD, DMbetaCD and TMbetaCD compared to 1.5% propylene glycol +3% Tween 80 (0.15 vs. 0.66-0.77). The viability of the EpiAirway tissues was significantly reduced by DMbetaCD and TMbetaCD formulations. This study showed that WIN 55,212-2 mesylate can be delivered via the nasal route. Absorption of R-(+)-WIN 55,212-2 was rapid and bioavailability was significantly improved using methylated cyclodextrins and propylene glycol-based cosolvent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Administration, Intranasal
  • Adult
  • Analgesics / administration & dosage
  • Analgesics / metabolism
  • Analgesics / pharmacokinetics
  • Animals
  • Area Under Curve
  • Benzoxazines / chemistry
  • Benzoxazines / metabolism
  • Benzoxazines / pharmacokinetics*
  • Bronchi / cytology
  • Bronchi / metabolism*
  • Cannabinoid Receptor Agonists*
  • Cell Culture Techniques
  • Cyclodextrins / chemistry
  • Half-Life
  • Humans
  • Injections, Intravenous
  • Male
  • Molecular Structure
  • Morpholines / chemistry
  • Morpholines / metabolism
  • Morpholines / pharmacokinetics*
  • Naphthalenes / chemistry
  • Naphthalenes / metabolism
  • Naphthalenes / pharmacokinetics*
  • Olfactory Mucosa / cytology
  • Olfactory Mucosa / metabolism
  • Permeability
  • Propylene Glycol / chemistry
  • Rats
  • Rats, Sprague-Dawley
  • Trachea / cytology
  • Trachea / metabolism*

Substances

  • Analgesics
  • Benzoxazines
  • Cannabinoid Receptor Agonists
  • Cyclodextrins
  • Morpholines
  • Naphthalenes
  • (3R)-((2,3-dihydro-5-methyl-3-((4-morpholinyl)methyl)pyrrolo-(1,2,3-de)-1,4-benzoxazin-6-yl)(1-naphthalenyl))methanone
  • Propylene Glycol