Advances in the Physicochemical Profiling of Opioid Compounds of Therapeutic Interest

Károly Mazák, B. Noszál, Sándor Hosztafi

Research output: Contribution to journalReview article

Abstract

This review focuses on recent developments in the physicochemical profiling of morphine and other opioids. The acid-base properties and lipophilicity of these compounds is discussed at the microscopic, species-specific level. Examples are provided where this type of information can reveal the mechanism of pharmacokinetic processes at the submolecular level. The role of lipophilicity in quantitative structure–activity relationship (QSAR) studies of opioids is reviewed. The physicochemical properties and pharmacology of the main metabolites of morphine are also discussed. Recent studies indicate that the active metabolite morphine-6-glucuronide (M6G) can contribute to the analgesic activity of systemically administered morphine. The unexpectedly high lipophilicity of M6G partly accounts for its analgesic activity. When administered parenterally, another suspected minor metabolite, morphine-6-sulfate (M6S) has superior antinociceptive effects to those of morphine. However, because sulfate esters of morphine derivatives cannot cross the blood-brain barrier these esters may be good candidates to develop peripheral analgesic drugs.

Original languageEnglish
Pages (from-to)879-887
Number of pages9
JournalChemistryOpen
Volume8
Issue number7
DOIs
Publication statusPublished - Jul 1 2019

Fingerprint

Morphine
Opioid Analgesics
Metabolites
Analgesics
Sulfates
Esters
Morphine Derivatives
Pharmacokinetics
Acids
morphine-6-glucuronide

Keywords

  • basicity
  • glucuronide conjugates
  • lipophilicity
  • opioids
  • physicochemical profiling

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Advances in the Physicochemical Profiling of Opioid Compounds of Therapeutic Interest. / Mazák, Károly; Noszál, B.; Hosztafi, Sándor.

In: ChemistryOpen, Vol. 8, No. 7, 01.07.2019, p. 879-887.

Research output: Contribution to journalReview article

Mazák, Károly ; Noszál, B. ; Hosztafi, Sándor. / Advances in the Physicochemical Profiling of Opioid Compounds of Therapeutic Interest. In: ChemistryOpen. 2019 ; Vol. 8, No. 7. pp. 879-887.
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