Advertisement

Pharmaceutisch weekblad

, Volume 3, Issue 1, pp 224–237 | Cite as

Transport in QSAR IV

The interfacial drug transfer model. Relationships between partition coefficients and rate constants of drug partitioning
  • J. Th. M. Van De Waterbeemd
  • C. C. A. A. Van Boekel
  • R. L. F. M. De Sévaux
  • A. C. A. Jansen
  • K. W. Gerritsma
Original Articles
First Online:

Abstract

A model for the interphase transfer of drugs is developed and theoretical relationships between partition coefficients and partitioning (transport) rate constants are derived.

A good agreement with experimental data from a series of sulfonamide derivatives is obtained. It is concluded that stagnant diffusion layers at the interface determine to a large extent the transfer rate constants.

Keywords

Homologous Series Gibbs Free Energy Diffusion Rate Constant Bilinear Equation Pharmaceutisch Weekblad Scientific Edition 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
This is a preview of subscription content, log in to check access.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Albery, W. J., andM. M. Kreevoy (1978)Advan. Phys. Org. Chem. 16, 87.Google Scholar
  2. Boom, J. H. van, P. M. J. Burgers, C. A. G. Haasnoot andC. B. Reese (1977)Rec. Trav. Chim. Pays Bas 96, 91.CrossRefGoogle Scholar
  3. BrØnsted, J. N., andK. Pedersen (1924)Z. Physik. Chem. 108, 185.Google Scholar
  4. Collander, R. (1954)Physiol. Plantarum 7, 420.CrossRefGoogle Scholar
  5. Craig, P.N. (1971)J. Med. Chem. 14, 680.CrossRefPubMedGoogle Scholar
  6. Dasler, W., andC. D. Bauer (1946)Ind. Eng. Chem. (Anal. Ed.) 18, 52.CrossRefGoogle Scholar
  7. Desnuelle, P., andG. Bonjour (1952)Biochim. Biophys. Acta 9, 356.CrossRefPubMedGoogle Scholar
  8. Dolby, L. J., C. A. Elliger, S. Esfandiari andK. S. Marshall (1968)J. Org. Chem. 33, 4508.CrossRefGoogle Scholar
  9. Draper, N. R., andH. Smith (1966)Applied regression analysis, John Wiley & Sons Ltd., New York.Google Scholar
  10. Eigen, M. (1963)Angew. Chem. 75, 489.CrossRefGoogle Scholar
  11. Flynn, G. L., andS. H. Yalkowsky (1972)J. Pharm. Sci. 61, 838.CrossRefPubMedGoogle Scholar
  12. Franke, R. (1979)Il Farmaco Ed. Sci. 34, 545.Google Scholar
  13. Gresham, T. L., J. E. Jansen andF. W. Shaver (1948)J. Am. Chem. Soc. 70, 1003;Ibidem (1950)72, 72.CrossRefGoogle Scholar
  14. Hamilton, C. S., andC. L. Simpson (1929)J. Am. Chem. Soc. 51, 3158.CrossRefGoogle Scholar
  15. Hammond, G. S. (1955)J. Am. Chem. Soc. 77, 334.CrossRefGoogle Scholar
  16. Hansch, C., andT. Fujita (1964)J. Am. Chem. Soc. 86, 1616.CrossRefGoogle Scholar
  17. Hassner, A., andV. Alexaniau (1978)Tetrahedron Letters 4475.Google Scholar
  18. Higuchi, T., andA. F. Michaelis (1968)Anal. Chem. 40, 1925.CrossRefGoogle Scholar
  19. Higuchi, T., andS. S. Davis (1970)J. Pharm. Sci. 59, 1376.CrossRefPubMedGoogle Scholar
  20. Holmberg, B. (1945)Arkiv Mineral. Geol. B 21, 7.Google Scholar
  21. Hunt, B. J., andW. Rigby (1967)Chem. Ind., 1868.Google Scholar
  22. Hyde, R. M. (1975)J. Med. Chem. 18, 231;Ibidem (1977)Chem. Ind., 859.CrossRefPubMedGoogle Scholar
  23. Hyde, R. M., andE. Lord (1979)Eur. J. Med. Chem. 14, 199.Google Scholar
  24. Ives, D. J. G., andK. Sames (1943)J. Chem. Soc., 516.Google Scholar
  25. Johnson, C. D. (1975)Chem. Rev. 75, 755.CrossRefGoogle Scholar
  26. Johnson, C. R., andJ. E. Keiser (1973)Organic Synthesis, Coll. Vol. V, 791.Google Scholar
  27. Jones, L. W., andD. H. Powers (1924)J. Am. Chem. Soc. 46, 2518.CrossRefGoogle Scholar
  28. Jones, R. A. Y. (1979)Physical and Mechanistic Organic Chemistry. Cambridge University Press, Cambridge.Google Scholar
  29. Koizumi, T., T., Arita andK. Kakemi (1964)Chem. Pharm. Bull. 12, 413.CrossRefPubMedGoogle Scholar
  30. Kresge, A. J. (1973)Chem. Soc. Rev. 2, 475.CrossRefGoogle Scholar
  31. Kubinyi, H. (1976)Arzneimittel-Forsch. 26, 1991;Ibidem (1978)J. Pharm. Sci. 67, 262;Ibidem (1979)Progr. Drug Res. 23, 98;Ibidem (1980) Personal communication.Google Scholar
  32. Kubinyi, H., andO. H. Kehrhahn (1978)Arnzneimittel-Forsch. 28, 598.Google Scholar
  33. Leffler, I. E. (1953)Science 117, 340.CrossRefPubMedGoogle Scholar
  34. Lehmkuhl, H., F. Rabet andK. Hauschild (1977)Synthesis, 185.Google Scholar
  35. Leslie, R. E., andH. K. Henze (1949)J. Am. Chem. Soc. 71, 3480.CrossRefGoogle Scholar
  36. Lewis, J. B. (1954)Chem. Eng. Sci. 3, 260.CrossRefGoogle Scholar
  37. Lippold, B. C., andG. F. Schneider (1975)Arzneimittel-Forsch. 25, 843, 1683;Ibidem (1976)Pharmazie 31, 237.Google Scholar
  38. Marcus, R. A. (1968)J. Phys. Chem. 72, 891.CrossRefGoogle Scholar
  39. Martin, Y. C., andJ. J. Hackbarth (1976)J. Med. Chem. 19, 1033.CrossRefPubMedGoogle Scholar
  40. Mcfarland, J. W. (1970)J. Med. Chem. 13, 1192.CrossRefPubMedGoogle Scholar
  41. Mietzsch, F., J. Klaren andR. Behnisch (1943)US Patent 2,335,599.Google Scholar
  42. Mooradian, A., C. J. Cavallito, A. J. Bergman, E. J. Lawson andC. M. Suter (1949)J. Am. Chem. Soc. 71, 3372.CrossRefGoogle Scholar
  43. Murdoch, J. R. (1972)J. Am. Chem. Soc. 94, 4410.CrossRefGoogle Scholar
  44. Neises, B., andW. Steglich (1978)Angew. Chem. 90, 556.CrossRefGoogle Scholar
  45. Nitsch, W. (1965)Ber. Bunsenges. Phys. Chem. 69, 884.CrossRefGoogle Scholar
  46. Nakatani, H., andH. B. Dunford (1979)J. Phys. Chem. 83, 2662.CrossRefGoogle Scholar
  47. Pross, A. (1977)Advan. Phys. Org. Chem. 14, 69.Google Scholar
  48. Rekker, R. F. (1977)The hydrophobic fragmental constant. Elsevier, Amsterdam.Google Scholar
  49. Rosen, H., A. Leaf andW. B. Schwartz (1964)J. Gen. Physiol. 48, 379.CrossRefPubMedPubMedCentralGoogle Scholar
  50. Scott, E. J., L. H. Tung andH. G. Drickamer (1951)J. Chem. Phys. 19, 1075.CrossRefGoogle Scholar
  51. Sekara, V. C., andC. S. Marvel (1933)J. Am. Chem. Soc. 55, 345.CrossRefGoogle Scholar
  52. Sonntag, N. O. V. (1953)Chem. Rev. 52, 237.CrossRefGoogle Scholar
  53. Stehle, R. G., andW. I. Higuchi (1972)J. Pharm. Sci. 61, 1922, 1931.CrossRefPubMedGoogle Scholar
  54. Suzuki, A., W. I. Higuchi andN. F. H. Ho (1970)J. Pharm. Sci. 59, 644, 651.CrossRefPubMedGoogle Scholar
  55. Vogel's textbook of practical organic chemistry, 4th Ed. (1978) Longman, London, 503, 492, 526.Google Scholar
  56. Waterbeemd, J. Th. M. Van De, A. C. A. Jansen andK. W. Gerritsma (1978)Pharm. Weekblad 113, 1097.Google Scholar
  57. Waterbeemd, J. Th. M. Van De, S. Van Boeckel, A. C. A. Jansen andK. W. Gerritsma (1980a)Eur. J. Med. Chem. 15, 279.Google Scholar
  58. Waterbeemd, J. Th. M. Van De, A. C. A. Jansen andK. W. Gerritsma (1980b)Pharm. Weekblad, Sci. Ed. 2, 73.Google Scholar
  59. Whitman, W. G. (1923)Chem. Met. Eng. 29, 147.Google Scholar
  60. Yalkowsky, S. H., andG. L. Flynn (1973)J. Pharm. Sci. 62, 210.CrossRefPubMedGoogle Scholar
  61. Zubrich, J. W., B. I. Dunbar andH. D. Durst (1975)Tetrahedron Letters, 71.Google Scholar

Copyright information

© Bohn, Scheltema & Holkema 1981

Authors and Affiliations

  • J. Th. M. Van De Waterbeemd
    • 1
  • C. C. A. A. Van Boekel
    • 1
  • R. L. F. M. De Sévaux
    • 1
  • A. C. A. Jansen
    • 1
  • K. W. Gerritsma
  1. 1.Department of Pharmacochemistry, Subfaculty of PharmacyUniversity of LeidenThe Netherlands

Personalised recommendations

Cite article

Buy options