Investigation of xenobiotic metabolism by CYP2D6 and CYP2C19: Importance of enantioselective analytical methods

Journal of Chromatography B: Biomedical Applications

Volumn 678, Issue 1, 1996, Pages 73-92

  Marzo, Antonio ^a   Balant, Luc P ^b  

^a IPAS SA   (Switzerland)

^b Service de Psychiatrie de l Enfant et de l Adolescent   (Switzerland)

Author keywords

CYP2D19; CYP2D6; Debrisoquine; Dextromethorphan; Enantiomer separation; Enzymes; Reviews; S Mephenytoin; Sparteine; Xenobiotics

Indexed keywords

ADRENERGIC RECEPTOR BLOCKING AGENT; ALPRENOLOL; AMITRIPTYLINE; CYTOCHROME P450 ISOENZYME; DEBRISOQUINE; DEXTROMETHORPHAN; MEPHENYTOIN; METOPROLOL; MIANSERIN; NORTRIPTYLINE; PROPRANOLOL; SPARTEINE;

ANIMAL MODEL; BIOASSAY; BIOEQUIVALENCE; CONTROLLED STUDY; DRUG DEVELOPMENT; DRUG TRANSFORMATION; ENANTIOMER; ENZYME ISOLATION; GAS CHROMATOGRAPHY; GENETIC POLYMORPHISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; IN VITRO STUDY; MASS SPECTROMETRY; PHENOTYPE; PRIORITY JOURNAL; RABBIT; REVIEW; TECHNIQUE; XENOBIOTIC METABOLISM;

EID: 0029916361     PISSN: 15726495     EISSN: None     Source Type: Journal    
DOI: 10.1016/0378-4347(95)00229-4     Document Type: Review

References (105)

1. L.P. Balant, U. Gundert-Remy, A.R. Boobis and C. von Bahr, Eur. J. Clin. Pharmacol., 36 (1989) 551.
2. I. Darmansjah and A. Muchtar, Clin. Pharmacol. Ther., 52 (1992) 449.
3. F. Sjöqvist, in S.G. Dahl and L.F. Gram (Editors), Clinical Pharmacology in Psychiatry. From Molecular Studies to Clinical Reality - Psychopharmacology Series 7, Springer-Verlag, Berlin, 1989, pp. 181-191.
4. L.P. Balant and P.G. Welling, in P.G. Welling and L.P. Balant (Editors), Handbook of Experimental Pharmacology, Vol. 110, Pharmacokinetics of Drugs, Springer-Verlag, Berlin, 1994, Chapter 8, pp. 233-263.
5. A. Marzo, Boll. Chim. Farm., 132 (1993) 267.
6. R. Bonicke and W. Reif, Arch. Exp. Pathol. Pharmacol., 220 (1953) 321.
7. D.A.P. Evans, K.A. Manley and V.A. McKusick, Br. Med. J., 2 (1960) 461.
8. W.W. Weber and D.W. Hein, Pharmacol. Rev., 37 (1985) 25.
9. D.W. Clark, Drugs, 29 (1985) 342.
10. D.A.P. Evans, Pharmacol. Ther., 42 (1989) 157.
11. D.A.P. Evans, in W. Kalow (Editor), Pharmacogenetics of Drug Metabolism, Pergamon Press, New York, 1992, pp. 95-178.
12. P.R. Bechtel and Y. Bechtel, in G. Alvan, L.P. Balant, P.R. Bechtel, A.R. Boobis, L.F. Gram and K. Pithan (Editors), European Consensus on Pharmacogenetics, Commission of the European Communities (Coordinated Action COST B1), Luxembourg, 1990, pp. 171-178.
13. U.A. Meyer, U.M. Zanger, D. Grant and M. Blum, in B. Testa (Editor) Advances in Drug Research, Academic Press, London, 1990, pp. 197-241.
14. L.P. Balant, A. Gorgia, J.M. Tschopp, C. Revillard and J. Fabre, Schweiz. Med. Wochenschr., 106 (1976) 1403.
15. P. Dayer, L. Balant, F. Courvoisier, A. Küpfer, A. Kubli, A. Gorgia and J. Fabre, Eur. J. Drug Metab. Pharmacokinet., 7 (1982) 73.
16. P. Dayer, L. Balant, A. Küpfer, F. Courvoisier and J. Fabre, Eur. J. Clin. Pharmacol., 24 (1983) 797.
17. A. Mahgoub, J.R. Idle, L.G. Dring, R. Lancester and R.L. Smith, Lancet, II (1977) 584.
18. M. Eichelbaum, N. Spannbrucker, B. Steincke and H.J. Dengler, Eur. J. Clin. Pharmacol., 16 (1979) 183.
19. G. Alvan, P. Bechtel and U. Gundert-Remy. Eur. J. Clin. Pharmacol., 39 (1990) 533.
20. M. Eichelbaum, Clin. Pharmacokinet., 7 (1982) 1.
21. M.S. Lennard, G.T. Tucker and H.F. Wood, Clin. Pharmacokinet., 11 (1986) 1.
22. F.J. Gonzalez, in W. Kalow (Editor), Pharmacogenetics of Drug Metabolism, Pergamon Press, New York, 1992, pp. 413-452.
23. F.J. Gonzalez and U.A. Meyer, Clin. Pharmacol. Ther., 50 (1991) 233.
24. U.A. Meyer, R.C. Skoda, U.M. Zanger, M. Heim and F. Broly, in W. Kalow (Editor), Pharmacogenetics of Drug Metabolism, Pergamon Press, New York, 1992, pp. 609-623.
25. K. Brøsen and L.F. Gram, Eur. J. Clin. Pharmacol., 36 (1989) 537.
26. M. Eichelbaum and A.S. Gross, in W. Kalow (Editor), Pharmacogenetics of Drug Metabolism, Pergamon Press, New York, 1992, pp. 625-648.
27. F. Sjöqvist, in W. Kalow (Editor), Pharmacogenetics of Drug Metabolism, Pergamon Press, New York, 1992, pp. 689-700.
28. H.K. Kroemer, G. Mikus and M. Eichelbaum, in P.G. Welling and L.P. Balant (Editors), Handbook of Experimental Pharmacology - Pharmacokinetics of Drugs, Springer-Verlag, Heidelberg, 1994, pp. 265-288.
29. A.E. Balant-Gorgia, L.P. Balant and G. Garrone, Ther. Drug Monit., 11 (1989) 415.
30. I. Roots, N. Drakoulis and J. Brockmöller, in W. Kalow (Editor), Pharmacogenetics of Drug Metabolism, Pergamon Press, New York, 1992, pp. 815-841.
31. O. Pelkonen, Scand. J. Work Environ. Health, 18 (1992) 17.
32. W. Kalow (Editor), Pharmacogenetics of Drug Metabolism, Pergamon Press, New York, 1992.
33. A. Küpfer, J. Bircher and R. Preisig, J. Pharmacol. Exp. Ther., 203 (1977) 493.
34. A. Küpfer, R.K. Roberts, S. Schenker and R.A. Branch, J. Pharmacol. Exp. Ther., 318 (1981) 193.
35. A. Küpfer, P. Desmond, S. Schenker and R.A. Branch, Pharmacologist, 21 (1979) 173.
36. A. Kupfer and R. Preisig, Eur. J. Clin. Pharmacol., 26 (1984) 753.
37. G.R. Wilkinson, F.P. Guengerich and R.A. Branch, in W. Kalow (Editor), Pharmacogenetics of Drug Metabolism, Pergamon Press, New York, 1992, pp. 657-685.
38. J.A. Goldstein, G.W. Wilkinson, K. Nakamura, U.A. Meyer and S.M.F. De Morais, J. Biol. Chem., 269 (1994) 15419.
39. T. Andersson, C.G. Regardh, Y.C. Lou, Y. Zhang, M.L. Dahl and L. Bertilsson, Pharmacogenetics, 2 (1992) 25.
40. S.A. Ward, N.A. Helsby, E. Skjelbo, K. Brøsen, L.F. Gram and A.M. Breckenridge, Br. J. Clin. Pharmacol., 31 (1991) 689.
41. A. Adedoyin, C. Prakash, D. O'Shea, I.A. Blair and G.R. Wilkinson, Pharmacogenetics, 4 (1994) 27.
42. A. Küpfer and R.A. Branch, Clin. Pharmacol. Ther., 38, (1985) 414.
43. S.H. Sindrup, K. Brøsen, M.G.J. Hansen, T. AaesJørgensen, K.F. Overø and L.F. Gram, Ther. Drug Monit., 13 (1993) 11.
44. S.A. Ward, T. Walle, U.K. Walle, G.R. Wilkinson and R.A. Branch, Clin. Pharmacol. Ther., 45 (1989) 72.
45. P. Baumann, M. Jonzier-Perey, L. Kerb, A. Küpfer, D. Tingueley and J. Schopf, Int. Clin. Psychopharmacol., 1 (1988) 102.
46. E. Skjelbo, K. Brøsen, J. Hallas and L.F. Gram, Clin. Pharmacol. Ther., 49 (1991) 18.
47. K. Kramer Nielsen, K. Brøsen, J. Hansen and L.F. Gram, Clin. Pharmacol. Ther., 55 (1994) 518.
48. L. Bertilsson, T.K. Henthorn, E. Sanz, G. Tybring, J. Säwe and T. Villén, Clin. Pharmacol. Ther., 45 (1989) 348.
49. Y. Horai, M. Nakano, T. Ishizaki, K. Ishikawa, H.H. Zhou, B.J. Zhou, C.L. Lia and L.M. Zhang, Clin. Pharmacol. Ther., 46 (1989) 198.
50. K. Nakamura, F. Goto, W.A. Ray, C.B. McAllister, E. Jacqz, G.R. Wilkinson and R.A. Branch, Clin. Pharmacol. Ther., 38 (1985) 402.
51. A. Kubli, L. Balant, P. Dayer, A. Balant-Gorgia and J. Fabre, J. Pharm. Clin., 1 (1982) 301.
52. P. Dayer, L. Balant, A. Küpfer, R. Striberni and T. Leemann, Eur. J. Clin. Pharmacol., 28 (1985) 317.
53. S. Vandel, G. Bertschy, B. Vandel, G. Allers and R. Volmat, Eur. J. Clin. Pharmacol., 37 (1989) 595.
54. A.E. Balant-Gorgia, P. Schulz, P. Dayer, L. Balant, A. Kubli, C. Gertsch and G. Garrone, Arch. Psychiatr. Nervenkr., 232 (1982) 215.
55. S. Vandel, G. Bertschy, B. Vandel, G. Allers and R. Volmat, Eur. J. Clin. Pharmacol., 39 (1990) 97.
56. M. Jerling and G. Alván, Eur. J. Clin. Pharmacol., 46 (1994) 67.
57. M. Bjerre, L.F. Gram, P. Kragh-Sørensen, C.B. Kristensen, O.L. Pedersen, M. Møller and P. Thayssen, Psychopharmacology, 75 (1981) 354.
58. K. Brøsen, R. Klysner, L.F. Gram, S.V. Otton, P. Bech and L. Bertilsson, Eur. J. Clin. Pharmacol., 30 (1986) 679.
59. S.H. Sindrup, K. Brøsen and L.F. Gram, Clin. Pharmacol. Ther., 51 (1992) 288.
60. J. Hermansson and C. von Bahr, J. Chromatogr., 227 (1982) 113.
61. M.S. Lennard, G.T. Tucker, J.H. Silas, S. Freestone, L.E. Ramsay and H.F. Woods, Clin. Pharmacol. Ther., 34 (1983) 732.
62. M.S. Lennard, in W. Kalow (Editor), Pharmacogenetics of Drug Metabolism, Pergamon Press, New York, 1992, pp. 701-720.
63. Annex XII, Pharmacokinetic studies in man, in Council Recommendation 87/176/EEC Concerning Tests Relating to the Placing on the Market of Proprietary Medicinal Products, Official Journal of the European Communities L73 (16 March 87).
64. U. Gundert-Remy, in G. Alvan, L.P. Balant, P.R. Bechtel, A.R. Boobis, L.F. Gram and K. Pithan (Editors), European Consensus on Pharmacogenetics, Commission of the European Communities (Coordinated Action COST B1), Luxembourg, 1990, pp. 129-134.
65. U. Gundert-Remy, in M. Rowland and L. Aarons (Editors), New Strategies in Drug Development and Clinical Evaluation: The Population Approach, Commission of the European Communities (Coordinated Action COST B1), Luxembourg, 1992, pp. 153-156.
66. C. von Bahr, C.G. Groth, H. Jansson, G. Lundgren, M. Lind and H. Glaumann, Clin. Pharmacol. Ther., 27 (1980) 711.
67. A.R. Boobis, M.J. Brodie, G.C. Kahn, D.R. Fletcher, J.H. Saunders and D.S. Davies, Br. J. Clin. Pharmacol., 9 (1980) 11.
68. P.J. Meier, H.K. Mueller, B. Dick and U.A. Meyer, Gastroenterology, 85 (1983) 682.
69. T. Inaba, R.E. Tyndale and W.A. Mahon, Br. J. Clin. Pharmacol., 22 (1986) 199.
70. C.J. Speirs, S. Murray, A.R. Boobis, C.E. Seddon and D.S. Davies, Br. J. Clin. Pharmacol., 22 (1986) 739.
71. A. Marzo, G. Cardace and E. Arrigoni Martelli, Chirality, 4 (1992)247.
72. A. Marzo, Boll. Chim. Farm., 128 (1989) 45.
73. K. Blau, in K. Blau and G.S. King (Editors), Handbook of Derivatives for Chromatography, Issue reprinted on demand by University Microfilms International, Ann Arbor, MI, 1986.
74. D.R. Knapp, Handbook of analytical derivatisation reactions, Wiley-Interscience, New York, 1979.
75. EU-Note for guidance: investigation of chiral active substances, CPMP Working party on quality of medicinal products, CPMP Working party on safety of medicinal products, CPMP Working party on efficacy of medicinal products, III/3601/91-EN-FINAL, April 1994.
76. A. Marzo, Arzneim. Forsch., 44 (1994) 791.
77. P. De Witt, R. Deias, S. Muck, B. Galletti, D. Meloni, P. Celletti and A. Marzo, J. Chromatogr. B, 657 (1994) 67.
78. A.M. Barrett and V.A. Cullum, Br. J. Pharmacol., 34 (1968) 43.
79. A. Marzo and J.D. Desager, Curr. Ther. Res., 30 (1981) 442.
80. A. Roux, G. Blanchot, A. Baglin and B. Flouvat. J. Chromatogr., 570 (1991) 435.
81. G.D. de Jongh, H.M. van den Wildenberg and F. van derVeen, Drug Metab. Dispos., 9 (1981) 48.
82. M.L. Dahl, G. Tybring, C.E. Elwin, C. Alm, K. Andreasson, M. Gyllenpalm and L. Bertilsson, Clin. Pharmacol. Ther., 56 (1994) 176.
83. C.B. Eap, K. Powell, D. Campus-Souche, C. Monney, D. Bealttig, W. Teaschner and P. Bauman, Chirality, 6 (1994) 555.
84. B. Mellström, L. Bertilsson, Y.C. Lou, J. Säwe and F. Sjöqvist, Clin. Pharmacol. Ther., 34 (1983) 516.
85. M. Åsberg, B. Cronholm, F. Sjöqvist and D. Tuck, Br. Med. J., 3 (1971) 331.
86. S.R. Biggs, L.F. Chasseaud, D.R. Hawkins and I. Midgley, Drug Metab. Dispos., 7 (1979) 233.
87. B. Vandel, M. Sandoz, S. Vandel, G. Allers and R. Valmat, Eur. J. Clin. Pharmacol., 22 (1982) 239.
88. B. Alexanderson and O. Borgå, Eur. J. Clin. Pharmacol., 5 (1973) 174.
89. G. Alván, O. Borgå, M. Lind, L. Palmér and B. Siwers, Eur. J. Clin. Pharmacol., 11 (1977) 219.
90. O. Borgå and M. Garle, J. Chromatogr., 68 (1972) 77.
91. L. Bertilsson and B. Alexanderson, Eur. J. Clin. Pharmacol., 4 (1972) 201.
92. B. Mellström, L. Bertilsson, J. Säwe, H.U. Shulz and F. Sjöqvist, Clin. Pharmacol. Ther., 30 (1981) 189.
93. B. Mellström and R. Braithwaite, J. Chromatogr., 157 (1978) 379.
94. J.L. Bock, E. Giller, S. Gray and P. Jatlow, Clin. Pharmacol. Ther., 31 (1982) 609.
95. M.L. Dahl, C. Nordin and L. Bertilsson, Ther. Drug Monit., 13 (1991) 189.
96. E. Nusser, K. Nill and U. Breyer-Pfaff, Drug Metab. Dispos., 16 (1988) 509.
97. E. Nusser, K. Nill and U. Breyer-Pfaff, J. Chromatogr., 528 (1990) 163.
98. B. Becher, W. Fischer, Z. Taneri, E. Scholz, W.E. Müller and U. Breyer-Pfaff, Psychopharmacology, 106 (1992) 303.
99. U. Breyer-Pfaff, B. Pfandl, K. Nill, E. Nusser, C. Monney, M. Jonzier-Perey, D. Baettig and P. Baumann, Clin. Pharmacol. Ther., 52 (1992) 350.
100. C.B. Eap, L. Koeb, E. Holsboer-Trachsler and P. Baumann, Ther. Drug Monit., 14 (1992) 380.
101. A. Marzo and L.P. Balant, Arzneim. Forsch., 45 (1995) 109.
102. EU-Note for guidance: Investigation of bioavailability and bioequivalence, CPMP working party on efficacy of medicinal products, III/54/89-EN-FINAL-December 1991.
103. Notice to applicants for marketing authorization for medicinal products for human use in the member states of the European Community, Volume IIA, 1993.
104. H.K. Kroemer, C. Funk-Brentano, D.J. Silberstein, A.J. J. Wood, M. Eichelbaum, R.L. Woosley and D.M. Roden, Circulation, 79 (1989) 1068.
105. L.A. Siddoway, K.A. Thompson, C.B. McAllister, T. Wang, G.R. Wilkinson, D.M. Rodey and R.L. Woosley, Circulation, 75 (1987) 785.