Structural attributes influencing unbound tissue distribution

Eur J Med Chem. 2020 Jan 1:185:111813. doi: 10.1016/j.ejmech.2019.111813. Epub 2019 Oct 28.

Abstract

Unbound tissue-to-plasma partition coefficients (Kpuu) were determined for 56 structurally diverse compounds in rats following intravenous infusion. Five tissues were included in the study: white adipose, brain, heart, liver, and skeletal muscle. The rank ordering of the median tissue Kpuu values was: liver (4.5) > heart (1.8) > adipose (1.2) > skeletal muscle (0.6) > brain (0.05), with liver being most enriched and brain most impaired. The median Kpuu values of acids and zwitterions were lower than those of bases and neutrals in all tissues but liver. Selective tissue distribution was observed, dependent upon chemotype, which demonstrated the feasibility of targeting or restricting drug exposure in certain tissues through rational design. Physicochemical attributes for Kpuu were identified using recursive partitioning, which further classified compounds with enriched or impaired tissue distribution. The attributes identified provided valuable insight on design principles for asymmetric tissue distribution to improve efficacy or reduce toxicity.

Keywords: Brain; Disposition; Drug design; Fraction unbound; Heart; K(puu); Liver; Metabolism; Pharmacokinetics; Skeletal muscle; Tissue unbound partition coefficient; Transporters; White adipose.

MeSH terms

  • Animals
  • Dose-Response Relationship, Drug
  • Infusions, Intravenous
  • Male
  • Models, Molecular
  • Molecular Structure
  • Organic Chemicals / administration & dosage
  • Organic Chemicals / chemistry
  • Organic Chemicals / pharmacokinetics*
  • Pharmaceutical Preparations / administration & dosage
  • Pharmaceutical Preparations / chemistry*
  • Rats
  • Rats, Wistar
  • Structure-Activity Relationship
  • Tissue Distribution

Substances

  • Organic Chemicals
  • Pharmaceutical Preparations