Association of mitotane with chylomicrons and serum lipoproteins: practical implications for treatment of adrenocortical carcinoma

Eur J Endocrinol. 2016 Mar;174(3):343-53. doi: 10.1530/EJE-15-0946. Epub 2015 Dec 15.

Abstract

Objective: Oral mitotane (o,p'-DDD) is a cornerstone of medical treatment for adrenocortical carcinoma (ACC).

Aim: Serum mitotane concentrations >14 mg/l are targeted for improved efficacy but not achieved in about half of patients. Here we aimed at a better understanding of intestinal absorption and lipoprotein association of mitotane and metabolites o,p'-dichlorodiphenylacetic acid (o,p'-DDA) and o,p'-dichlorodiphenyldichloroethane (o,p'-DDE).

Design: Lipoproteins were isolated by ultracentrifugation from the chyle of a 29-year-old patient and serum from additional 14 ACC patients treated with mitotane. HPLC was applied for quantification of mitotane and metabolites. We assessed NCI-H295 cell viability, cortisol production, and expression of endoplasmic reticulum (ER) stress marker genes to study the functional consequences of mitotane binding to lipoproteins.

Results: Chyle of the index patient contained 197 mg/ml mitotane, 53 mg/ml o,p'-DDA, and 51 mg/l o,p'-DDE. Of the total mitotane in serum, lipoprotein fractions contained 21.7±21.4% (VLDL), 1.9±0.8% (IDL), 8.9±5.5% (LDL1), 18.9±9.6% (LDL2), 10.1±4.0% (LDL3), and 26.3±13.0% (HDL2). Only 12.3±5.5% were in the lipoprotein-depleted fraction.

Discussion: Mitotane content of lipoproteins directly correlated with their triglyceride and cholesterol content. O,p'-DDE was similarly distributed, but 87.9±4.2% of o,p'-DDA found in the HDL2 and lipoprotein-depleted fractions. Binding of mitotane to human lipoproteins blunted its anti-proliferative and anti-hormonal effects on NCI-H295 cells and reduced ER stress marker gene expression.

Conclusion: Mitotane absorption involves chylomicron binding. High concentrations of o,p'-DDA and o,p'-DDE in chyle suggest intestinal mitotane metabolism. In serum, the majority of mitotane is bound to lipoproteins. In vitro, lipoprotein binding inhibits activity of mitotane suggesting that lipoprotein-free mitotane is the therapeutically active fraction.

Publication types

  • Case Reports
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adrenal Cortex Neoplasms / drug therapy*
  • Adrenocortical Carcinoma / drug therapy*
  • Adult
  • Aged
  • Antineoplastic Agents, Hormonal / metabolism*
  • Antineoplastic Agents, Hormonal / pharmacology
  • Antineoplastic Agents, Hormonal / therapeutic use
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Chromatography, High Pressure Liquid
  • Chyle / chemistry
  • Chylomicrons / metabolism*
  • Cohort Studies
  • Endoplasmic Reticulum Stress / drug effects
  • Female
  • Gastrointestinal Absorption
  • Humans
  • Lipoproteins / metabolism*
  • Lipoproteins / pharmacology
  • Lipoproteins, HDL2 / metabolism
  • Lipoproteins, IDL / metabolism
  • Lipoproteins, LDL / metabolism
  • Lipoproteins, VLDL / metabolism
  • Male
  • Middle Aged
  • Mitotane / analogs & derivatives
  • Mitotane / metabolism*
  • Mitotane / pharmacology
  • Mitotane / therapeutic use

Substances

  • Antineoplastic Agents, Hormonal
  • Chylomicrons
  • Lipoproteins
  • Lipoproteins, HDL2
  • Lipoproteins, IDL
  • Lipoproteins, LDL
  • Lipoproteins, VLDL
  • 2,2-(2-chlorophenyl-4'-chlorophenyl)acetic acid
  • Mitotane
  • 2,2-(2-chlorophenyl-4'-chlorophenyl)-1,1-dichloroethene