Design, synthesis, and biological evaluation of 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-[(4'-pyridyl)carboxamido]morphinan derivatives as peripheral selective μ opioid receptor Agents

J Med Chem. 2012 Nov 26;55(22):10118-29. doi: 10.1021/jm301247n. Epub 2012 Nov 9.

Abstract

Peripheral selective μ opioid receptor (MOR) antagonists could alleviate the symptoms of opioid-induced constipation (OIC) without compromising the analgesic effect of opioids. However, a variety of adverse effects were associated with them, partially due to their relatively low MOR selectivity. NAP, a 6β-N-4'-pyridyl substituted naltrexamine derivative, was identified previously as a potent and highly selective MOR antagonist mainly acting within the peripheral nervous system. The noticeable diarrhea associated with it prompted the design and synthesis of its analogues in order to study its structure-activity relationship. Among them, compound 8 showed improved pharmacological profiles compared to the original lead, acting mainly at peripheral while increasing the intestinal motility in morphine-pelleted mice (ED(50) = 0.03 mg/kg). The slight decrease of the ED(50) compared to the original lead was well compensated by the unobserved adverse effect. Hence, this compound seems to be a more promising lead to develop novel therapeutic agents toward OIC.

Publication types

  • Evaluation Study
  • Research Support, N.I.H., Extramural

MeSH terms

  • Analgesics / chemical synthesis
  • Analgesics / pharmacokinetics
  • Analgesics / pharmacology
  • Animals
  • Caco-2 Cells
  • Drug Design*
  • Gastrointestinal Motility / drug effects*
  • Humans
  • Male
  • Mice
  • Models, Molecular
  • Molecular Structure
  • Morphinans / chemical synthesis*
  • Morphinans / pharmacokinetics
  • Morphinans / pharmacology*
  • Morphine Derivatives / chemical synthesis*
  • Morphine Derivatives / pharmacokinetics
  • Morphine Derivatives / pharmacology*
  • Narcotic Antagonists / chemical synthesis*
  • Narcotic Antagonists / pharmacokinetics
  • Narcotic Antagonists / pharmacology*
  • Radioligand Assay
  • Receptors, Opioid, mu / antagonists & inhibitors*
  • Receptors, Opioid, mu / metabolism
  • Structure-Activity Relationship
  • Tissue Distribution

Substances

  • 17-cyclopropylmethyl-3,14-dihydroxy-4,5-epoxy-6-((4'-(3'-methylpyridyl))carboxamido)morphinan
  • Analgesics
  • Morphinans
  • Morphine Derivatives
  • Narcotic Antagonists
  • Receptors, Opioid, mu