Prediction of solubility of drugs and other compounds in organic solvents

  1. Michael H. Abraham1,*,
  2. Robert E. Smith2,3,
  3. Ron Luchtefeld2,
  4. Aaron J. Boorem3,
  5. Rensheng Luo4,
  6. William E. Acree Jr.5

Article first published online: 22 SEP 2009

DOI: 10.1002/jps.21922

Issue

Journal of Pharmaceutical Sciences

Journal of Pharmaceutical Sciences

Volume 99, Issue 3, pages 1500–1515, March 2010

Additional Information

How to Cite

Abraham, M. H., Smith, R. E., Luchtefeld, R., Boorem, A. J., Luo, R. and Acree, W. E. (2010), Prediction of solubility of drugs and other compounds in organic solvents. Journal of Pharmaceutical Sciences, 99: 1500–1515. doi: 10.1002/jps.21922

Author Information

  1. 1

    Department of Chemistry, University College London, 20 Gordon Street, London WC1H OAJ, UK

  2. 2

    Total Diet and Pesticide Research Center, US Food and Drug Administration, West 80th Street, Lenexa, Kansas 66214

  3. 3

    Chemistry Department, Park University, 8700 Northwest River Park Drive, Parkville, Missouri 64152

  4. 4

    Department of Chemistry and Biochemistry, University of Missouri – St. Louis, One University Drive, St. Louis, Missouri 63121

  5. 5

    Department of Chemistry, University of North Texas, 1155 Union Circle Drive #305070, Denton, Texas 76203-5017

*Department of Chemistry, University College London, 20 Gordon Street, London WC1H OAJ, UK. Telephone: 44-20-7679-4639; Fax: 44-20-7679-7463.

Publication History

  1. Issue published online: 7 JAN 2010
  2. Article first published online: 22 SEP 2009
  3. Manuscript Accepted: 31 JUL 2009
  4. Manuscript Received: 30 APR 2009

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Keywords:

  • physicochemical properties;
  • solubility;
  • structure–property relationship (SPR);
  • distribution;
  • QSPR

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

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