Searching for Synthetic Opioid Rescue Agents: Identification of a Potent Opioid Agonist with Reduced Respiratory Depression

J Med Chem. 2024 Jun 13;67(11):9173-9193. doi: 10.1021/acs.jmedchem.4c00333. Epub 2024 May 29.

Abstract

While in the process of designing more effective synthetic opioid rescue agents, we serendipitously identified a new chemotype of potent synthetic opioid. Here, we report that conformational constraint of a piperazine ring converts a mu opioid receptor (MOR) antagonist into a potent MOR agonist. The prototype of the series, which we have termed atoxifent (2), possesses potent in vitro agonist activity. In mice, atoxifent displayed long-lasting antinociception that was reversible with naltrexone. Repeated dosing of atoxifent produced antinociceptive tolerance and a level of withdrawal like that of fentanyl. In rats, while atoxifent produced complete loss of locomotor activity like fentanyl, it failed to produce deep respiratory depression associated with fentanyl-induced lethality. Assessment of brain biodistribution demonstrated ample distribution of atoxifent into the brain with a Tmax of approximately 0.25 h. These results indicate enhanced safety for atoxifent-like molecules compared to fentanyl.

MeSH terms

  • Analgesics, Opioid* / chemical synthesis
  • Analgesics, Opioid* / chemistry
  • Analgesics, Opioid* / pharmacology
  • Animals
  • Brain / drug effects
  • Brain / metabolism
  • Fentanyl* / chemical synthesis
  • Fentanyl* / chemistry
  • Fentanyl* / pharmacology
  • Humans
  • Male
  • Mice
  • Naltrexone / analogs & derivatives
  • Naltrexone / chemical synthesis
  • Naltrexone / chemistry
  • Naltrexone / pharmacology
  • Naltrexone / therapeutic use
  • Piperazines / chemical synthesis
  • Piperazines / chemistry
  • Piperazines / pharmacokinetics
  • Piperazines / pharmacology
  • Piperazines / therapeutic use
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Opioid, mu* / agonists
  • Receptors, Opioid, mu* / metabolism
  • Respiratory Insufficiency* / chemically induced
  • Respiratory Insufficiency* / drug therapy
  • Structure-Activity Relationship
  • Tissue Distribution

Substances

  • Receptors, Opioid, mu
  • Analgesics, Opioid
  • Fentanyl
  • Piperazines
  • Naltrexone