Get access

Prediction of solubility of drugs and other compounds in organic solvents

Authors

  • Michael H. Abraham,

    Corresponding author
    1. Department of Chemistry, University College London, 20 Gordon Street, London WC1H OAJ, UK
    • Department of Chemistry, University College London, 20 Gordon Street, London WC1H OAJ, UK. Telephone: 44-20-7679-4639; Fax: 44-20-7679-7463.
    Search for more papers by this author
  • Robert E. Smith,

    1. Total Diet and Pesticide Research Center, US Food and Drug Administration, West 80th Street, Lenexa, Kansas 66214
    2. Chemistry Department, Park University, 8700 Northwest River Park Drive, Parkville, Missouri 64152
    Search for more papers by this author
  • Ron Luchtefeld,

    1. Total Diet and Pesticide Research Center, US Food and Drug Administration, West 80th Street, Lenexa, Kansas 66214
    Search for more papers by this author
  • Aaron J. Boorem,

    1. Chemistry Department, Park University, 8700 Northwest River Park Drive, Parkville, Missouri 64152
    Search for more papers by this author
  • Rensheng Luo,

    1. Department of Chemistry and Biochemistry, University of Missouri – St. Louis, One University Drive, St. Louis, Missouri 63121
    Search for more papers by this author
  • William E. Acree Jr.

    1. Department of Chemistry, University of North Texas, 1155 Union Circle Drive #305070, Denton, Texas 76203-5017
    Search for more papers by this author

Abstract

We have set out a procedure for the prediction of solubilities of drugs and other compounds in a wide range of solvents, based on the Abraham solvation equations. The method requires a knowledge of solubilities of a given compound in a few solvents, as shown by our own experimental data on apocynin, diapocynin, dehydrodivanillin, and dehydrodi(methyl vanillate). The procedure is especially useful for very hydrophobic compounds such as cholesteryl acetate and cholesterol that we give as examples. Other examples include vanillin and 3,4-dichlorobenzoic acid. If the solubility in water is available, then this alone is sufficient to predict solubilities in organic solvents, provided that the Abraham descriptors are available for the compound. Predictions can be made for solubilities in some 85 solvents. © 2009 Wiley-Liss, Inc. and the American Pharmacists Association J Pharm Sci 99: 1500–1515, 2010

Ancillary