Pharmacological profiles of fentanyl analogs at mu, delta and kappa opiate receptors

Eur J Pharmacol. 1992 Mar 24;213(2):219-25. doi: 10.1016/0014-2999(92)90685-w.

Abstract

Receptor binding assays using [3H]DAGO ([D-Ala2,MePhe4-Gly5-ol]enkephalin) (mu), [3H]DPDPE ([D-Pen2,D-Pen5]enkephalin) (delta) and [3H]U-69593 (kappa) were done in guinea pig whole brain membranes. Agonist activity was determined in norbinaltorphimine or beta-funaltrexamine (beta-FNA) treated guinea pig ileum (mu and kappa, respectively) and beta-FNA-treated mouse vas deferens (delta). The compounds with highest affinity were the most potent at the mu-receptor. The selectivity observed in the binding affinities was also found in in vitro activity. No correlation was found between mu-affinity and selectivity; the highest affinity analog, lofentanil, was found to be among the least selective, while another high affinity analog, R30490, was the most mu-selective. The results show that not all fentanyls are highly mu-selective, and could produce actions through delta- and kappa-opiate receptors.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Analgesics, Opioid / metabolism
  • Animals
  • Benzeneacetamides*
  • Brain / metabolism
  • Enkephalin, Ala(2)-MePhe(4)-Gly(5)-
  • Enkephalin, D-Penicillamine (2,5)-
  • Enkephalins / metabolism*
  • Fentanyl / analogs & derivatives*
  • Fentanyl / metabolism
  • Guinea Pigs
  • Ileum / drug effects
  • Ileum / metabolism
  • Male
  • Mice
  • Naltrexone / analogs & derivatives
  • Naltrexone / pharmacology
  • Pyrrolidines / metabolism*
  • Receptors, Opioid / metabolism*
  • Receptors, Opioid, delta
  • Receptors, Opioid, kappa
  • Receptors, Opioid, mu
  • Vas Deferens / drug effects
  • Vas Deferens / metabolism

Substances

  • Analgesics, Opioid
  • Benzeneacetamides
  • Enkephalins
  • Pyrrolidines
  • Receptors, Opioid
  • Receptors, Opioid, delta
  • Receptors, Opioid, kappa
  • Receptors, Opioid, mu
  • Enkephalin, Ala(2)-MePhe(4)-Gly(5)-
  • norbinaltorphimine
  • Naltrexone
  • 4-methoxymethylfentanyl
  • beta-funaltrexamine
  • lofentanil
  • Enkephalin, D-Penicillamine (2,5)-
  • U 69593
  • Fentanyl