Encyclopedia of Psychopharmacology

Living Edition
| Editors: Ian P. Stolerman, Lawrence H. Price

Lipophilicity

  • Craig W. LindsleyEmail author
Living reference work entry
DOI: https://doi.org/10.1007/978-3-642-27772-6_7015-1
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Synonyms

Hydrophobicity; Nonpolarity

Definition

Lipophilicity, or “fat friendly” as derived from the Greek, is described as the degree to which an organic molecule dissolves in fat, oil, or nonpolar organic solvents (i.e., hexanes), as opposed to polar solvents (i.e., water). Of all the physiochemical properties measured and monitored in a chemical optimization program en route to a drug candidate, lipophilicity is the most important, as it influences ligand–target binding interactions, solubility, ADME (absorption, distribution, metabolism, and elimination) properties, as well as in vivo toxicological outcomes, and, therefore, the overall quality of the drug candidate. Historically, LogP, the partition coefficient of a molecule between octanol (lipophilic phase) and water (hydrophilic phase), was used to measure lipophilicity; however LogD, the LogP at pH 7.4 (the physiological pH of blood serum), is now often employed to more accurately account for charged molecules. Recently,...

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Copyright information

© Springer-Verlag Berlin Heidelberg 2014

Authors and Affiliations

  1. 1.Departments of Pharmacology & ChemistryVanderbilt University Medical Center, Vanderbilt Center for Neuroscience Drug DiscoveryNashvilleUSA