Ionic partition diagrams of ionisable drugs: PH-lipophilicity profiles, transfer mechanisms and charge effects on solvation

Journal of Electroanalytical Chemistry

Volumn 462, Issue 2, 1999, Pages 235-250

  Reymond, Frédéric ^a   Chopineaux Courtois, Véronique ^a   Steyaert, Guillaume ^b   Bouchard, Géraldine ^b   Carrupt, Pierre Alain ^b   Testa, Bernard ^b   Girault, Hubert H ^a  

^a EPFL   (Switzerland)

^b UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

Diclofenac; Hydralazine; ITIES; Lauric acid; Lipophilicity; Nicotine; Phenylalanine; Pyridine

Indexed keywords

CHARGE TRANSFER; CHLORINE COMPOUNDS; CYCLIC VOLTAMMETRY; DISSOCIATION; GIBBS FREE ENERGY; INTERFACES (MATERIALS); IONIZATION; PH EFFECTS; REACTION KINETICS; WATER;

DICHLOROETHANE; IONIC PARTITION DIAGRAMS; LIPOPHILICITY; PARTITION COEFFICIENTS;

DRUG PRODUCTS;

EID: 0033075350     PISSN: 15726657     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-0728(98)00418-5     Document Type: Article

References (77)

1. Valvani S.C., Yalkowsky S.H. Solubility and partitioning in drug design. Valvani S.C., Sinkula A.A., Yalkowsky S.H. Physical Chemical Properties of Drugs. 10:1980;201 Marcel Dekker, New York.
2. Conradi R.A., Burton P.S., Borchardt R.T. Physico-chemical and biological factors that influence a drug's cellular permeability by passive diffusion. Pliska V., Testa B., van de Waterbeemd H. Lipophilicity in Drug Action and Toxicology. 4:1996;233 VCH, Weinheim.
3. Reymond F., Steyaert G., Carrupt P.-A., Testa B., Girault H.H. Helv. Chim. Acta. 79:1996;101.
4. Reymond F., Steyaert G., Pagliara A., Carrupt P.-A., Testa B., Girault H. Helv. Chim. Acta. 79:1996;1651.
5. Senda M., Kakiuchi T., Osakai T. Electrochim. Acta. 36:1991;253.
6. Girault H.H. Charge transfer across liquid liquid interfaces. Bockris J.O. M., Conway B., White R. Modern Aspects of Electrochemistry. 25:1993;1 Plenum Press, New York.
7. Shirai O., Yoshida Y., Matsui M., Maeda K., Kihara S. Bull. Chem. Soc. Jpn. 69:1996;3151.
8. Ding L., Wang E. Electroanalysis. 8:1996;922.
9. Houk J., Guy R.H. Chem. Rev. 88:1988;455.
10. Kontturi K., Murtomäki L. J. Controlled Release. 41:1996;177.
11. Senda M. Anal. Sci. Technol. 8:1995;95A.
12. Arai K., Kusu F., Takamura K. Electrochemical behavior of drugs at oil water interfaces. Volkov A. G., Deamer D. W. Liquid Liquid Interfaces. Theory and Methods. 1996;375 CRC Press, Boca Raton.
13. Ohkouchi T., Kakutani T., Senda M. Bioelectrochem. Bioenerg. 25:1991;71.
14. Doe H., Yoshioka K., Kitagawa T. J. Electroanal. Chem. 324:1992;69.
15. Matsuda H., Yamada Y., Kanamori K., Kudo Y., Takeda Y. Bull. Chem. Soc. Jpn. 64:1991;1497.
16. Reymond F., Steyaert G., Carrupt P.-A., Testa B., Girault H.H. J. Am. Chem. Soc. 118:1996;11951.
17. Arai K., Ohsawa M., Kusu F., Takamura K. Bioelectrochem. Bioenerg. 31:1993;65.
18. Kontturi K., Murtomaki L. J. Pharm. Sci. 81:1992;970.
19. M.H. Abraham, Chem. Soc. Rev. (1993) 73.
20. Testa B., Carrupt P.-A., Gaillard P., Billois F., Weber P. Pharm. Res. 13:1996;335.
21. Steyaert G., Lisa G., Carrupt P.-A., Testa B., Reymond F., Girault H.H. J. Chem. Soc. Faraday Trans. 93:1997;401.
22. F. Reymond, H.H. Girault, in preparation.
23. Bard A.J., Faulkner L.R. Electrochemical Methods: Fundamentals and Applications. 1980;Wiley, New York.
24. International program on chemical safety (Ed.), 1,2-Dichloroethane, World Health Organization, Geneva, 1995.
25. Wandlowski T., Marecek V., Samec Z. Electrochim. Acta. 35:1990;1173.
26. Kubota Y., Katano H., Maeda K., Senda M. Electrochim. Acta. 44:1998;109.
27. Shao Y., Osborne M.D., Girault H.H. J. Electroanal. Chem. 318:1991;101.
28. G. Steyaert, Intérêt en Chimie Thérapeutique de la Lipophilie d'Espèces Ioniques, Ph.D. Thesis, University of Lausanne, Lausanne, 1998.
29. Rekker R.F., Mannhold R. Calculation of Drug Lipophilicity. The Hydrophobic Fragmental Approach. 1992;VCH, Weinheim.
30. F. Reymond, P.-A. Carrupt, B. Testa, H.H. Girault, Chem. Eur. J. (1999) in press.
31. Aungst B.J., Blake J.A., Hussain M.A. Pharm. Res. 7:1990;712.
32. Cumming K.I., Winfield A.J. Int. J. Pharm. 108:1994;141.
33. Golden G.M., McKie J.E., Potts R.O. J. Pharm. Sci. 76:1987;25.
34. Green P.G., Guy R.H., Hadgraft J. Int. J. Pharm. 48:1988;103.
35. Green P.G., Hadgraft J., Ridout G. Pharm. Res. 6:1989;628.
36. Smith S.W., Anderson B.D. J. Pharm. Sci. 84:1995;551.
37. J.M. Ritter, L.D. Lewis, T.G.K. Mast (Eds.), A Textbook of Clinical Pharmacology, Arnold, New York, 1995.
38. Lin S.S., Ho H., Chien Y.W. J. Controlled Release. 26:1993;175.
39. Oakley D.M., Swarbrick J. J. Pharm. Sci. 76:1987;866.
40. Nair M.K., Chetty D.J., Ho H., Chien Y.W. J. Pharm. Sci. 86:1997;257.
41. V. Chopineaux-Courtois, S. Lemoult, P.-A. Carrupt, D. Schiffrin, H.H. Girault, Chem. Commun., in press.
42. Reece P.A. Med. Res. Rev. 1:1985;73.
43. Azuma J., Sawamura A., Harada H., Awata N., Kishimoto S., Sperelakis N. Eur. J. Pharmacol. 135:1987;137.
44. Tracy J.W., Webster L.T. Drugs used in the chemotherapy of protozoal infections: malaria. Hardman J.G., Limbird L.E., Molinoff P.B., Ruddon R.W. The Pharmacological Basis of Therapeutics. 1995;965 McGraw-Hill, New York.
45. Rubin L.J., Peter R.H. New Engl. J. Med. 302:1980;69.
46. Reeves J.T. New Engl. J. Med. 302:1980;112.
47. O'Malley K., Segal J.L., Israili Z.H., Boles M., McNay J.L., Dayton P.G. Clin. Pharmac. Ther. 18:1975;581.
48. Moore-Jones D., Perry H.M. Proc. Soc. Exp. Biol. Med. 122:1966;576.
49. Haegele K.D., Skrdlant H.B., Robie N.W., Lalka D., McNay J.K. J. Chromatogr. 126:1976;517.
50. Reece P.A., Stanley P.E., Zacest R. J. Pharm. Sci. 67:1978;1150.
51. Naik D.V., Davis B.R., Minnet K.M., Schulman G. J. Pharm. Sci. 65:1976;274.
52. J.E.F. Reynolds (Ed.) Martindale: The Extra Pharmacopoeia, The Pharmaceutical Press, London, 1982.
53. Pagliara A., Carrupt P.-A., Caron G., Gaillard P., Testa B. Chem. Rev. 97:1997;3385.
54. Anderson J.A., Graven H., Ertel R., Fisch R. J. Pediatr. 61:1962;603.
55. Huang T., Warsinke A., Kuwana T., Scheller F.W. Anal. Chem. 70:1998;991.
56. Bessmann S.P. Nutrition Rev. 37:1979;209.
57. Prasad C., Dalton L., Levy H. Nutrition Res. 18:1998;391.
58. W.M. Pardridge (Ed.) An Introduction to the Blood-Brain Barrier: Methodology and Biology, Cambridge University Press, Cambridge, 1998.
59. Binek-Singer P., Johnson T.C. Biochem. J. 206:1982;407.
60. Choi T., Pardridge W.M. J. Biol. Chem. 261:1986;6536.
61. Pardridge W.M. Phenylalanine transport at the human blood-brain barrier. Kaufmann S. Amino Acids in Health and Disease: New Perspectives. 1987;43 Liss, New York.
62. Wall K.M., Pardridge W.M. Biochem. Biophys. Res. Comm. 168:1990;1177.
63. Pardridge W.M. Neurochem. Res. 23:1998;635.
64. Möller H.E., Weglage J., Wiedermann D., Vermathen P., Bick U., Ullrich K. Brain Res. 778:1997;329.
65. Knudsen G.M., Hasselbalch S., Toft P.B., Christensen E., Paulson O.B., Lou H. J. Inher. Metab. Dis. 18:1995;653.
66. Pagliara A., Testa B., Carrupt P.-A., Jolliet P., Morin C., Morin D., Urien S., Tillement J.-P., Rihoux J.-P. J. Med. Chem. 41:1998;853.
67. Young R.C., Mitchell R.C., Brown T.H., Ganellin C.R., Griffiths R., Jones M., Rana K.K., Saunders D., Smith I.R., Sore N.E., Wilks T.J. J. Med. Chem. 31:1988;656.
68. ter Laak T., Tsai R.-S., Donné-Op den Kelder G.M., Carrupt P.-A., Testa B., Timmerman H. Eur. J. Pharm. Sci. 2:1994;373.
69. Fauchère J.-L. Lipophilicity in peptide chemistry and peptide drug design. Pliska V., Testa B., van de Waterbeemd H. Lipophilicity in Drug Action and Toxicology. 1996;355 VCH, Weinheim.
70. Abraham M.H., Danil de Namor A.F. J. Chem. Soc. Faraday Trans. 172:1976;955.
71. Czapkiewicz J., Czapkiewicz-Tutaj B. J. Chem. Soc. Faraday Trans. 176:1980;1663.
72. Sabela A., Marecek V., Samec Z., Fuoco R. Electrochim. Acta. 37:1992;231.
73. Shao Y., Weber S.G. J. Phys. Chem. 100:1996;14714.
74. Clarke F.H. J. Pharm. Sci. 73:1984;226.
75. Cordell G.A. Introduction to Alkaloids: A Biogenic Approach. 1981;Wiley, New York.
76. El Tayar N., Tsai R.-S., Carrupt P.-A., Testa B. J. Chem. Soc. Perkin Trans. 2:1992;79.
77. Shao Y., Stewart A.A., Girault H.H. J. Chem. Soc. Farad. Trans. 87:1991;2593.