The Impact of Lipophilicity in Drug Discovery: Rapid Measurements by Means of Reversed-Phase HPLC

Methods Mol Biol. 2018:1824:217-228. doi: 10.1007/978-1-4939-8630-9_12.

Abstract

Lipophilicity constitutes a vital physicochemical property in drug design as it is connected with pharmacodynamic and pharmacokinetic properties as well as toxicological aspects of candidate drugs. Traditional partitioning experiments to determine n-octanol-water coefficients are laborious and time-consuming, while they cannot be reliably performed for highly lipophilic or compounds undergoing degradation. Alternatively, lipophilicity of candidate drugs can be accurately and reproducibly determined using reversed-phase liquid chromatography. In this chapter, the details of protocols for lipophilicity assessment using reversed-phase HPLC, under conditions which provide the best simulation of n-octanol-water partition coefficients, are described.

Keywords: Extrapolated retention factors; Lipophilicity; Reversed-phase HPLC; n-Octanol as mobile phase additive; n-Octanol-water partition coefficient.

MeSH terms

  • 1-Octanol / chemistry
  • Chromatography, High Pressure Liquid / instrumentation
  • Chromatography, High Pressure Liquid / methods
  • Chromatography, Reverse-Phase / instrumentation
  • Chromatography, Reverse-Phase / methods
  • Drug Design*
  • Drug Discovery / instrumentation
  • Drug Discovery / methods*
  • Humans
  • Water / chemistry

Substances

  • Water
  • 1-Octanol