Characterization of human metabolism and disposition of levo-tetrahydropalmatine: Qualitative and quantitative determination of oxidative and conjugated metabolites

J Pharm Biomed Anal. 2016 Sep 5:128:371-381. doi: 10.1016/j.jpba.2016.06.015. Epub 2016 Jun 9.

Abstract

Levo-tetrahydropalmatine (l-THP) is a tetrahydroprotoberberine isoquinoline alkaloid and has been used as an analgesic agent in China for over 50 years. Recent studies revealed that l-THP was effective in the treatment of drug addiction. However, the plasma metabolic profile, mass balance and clearance pathways of l-THP in human remain unknown. In the present study, an analytical strategy was developed for qualitative and quantitative investigation of metabolism and disposition of l-THP in human. Detection and structural characterization of l-THP metabolites were performed using liquid chromatography-quadrupole time-of-flight mass spectrometry. Selected major metabolites in plasma, urine and feces determined by liquid chromatography with UV detection were further quantified using a triple quadruple mass spectrometry and reference standards. A total of 20 metabolites were identified, most of which were formed via demethylation, mono-hydroxylation, and glucuronidation and sulfonation of desmethyl metabolites. Five major metabolites accounted for over 10% of the parent drug concentration in plasma. Major urinary and fecal metabolites and the parent drug that were monitored for 72h accounted for 46.3% of the dose, while only 0.16% of the dose was the unchanged drug. Multiple demethylations followed by glucuronide and sulfate conjugations and renal excretion were the major drug clearance pathways of l-THP in human.

Keywords: Disposition; Human; LC–MS/MS; Levo-tetrahydropalmatine; Metabolism; QTOF-MS/MS.

MeSH terms

  • Adult
  • Berberine Alkaloids / blood
  • Berberine Alkaloids / pharmacokinetics*
  • Berberine Alkaloids / urine
  • Chromatography, High Pressure Liquid
  • Feces / chemistry
  • Humans
  • Male
  • Tandem Mass Spectrometry

Substances

  • Berberine Alkaloids
  • tetrahydropalmatine