Role of CYP2D6 in the N-hydroxylation of procainamide

Pharmacogenetics

Volumn 7, Issue 5, 1997, Pages 381-390

  Lessard, Étienne ^a   Fortin, Anne ^a   Bélanger, Pierre Maxime ^a   Beaune, Philippe ^b   Hamelin, Bettina A ^a   Turgeon, Jacques ^a  

^a LAVAL UNIVERSITY   (Canada)

^b HÔPITAL NECKER ENFANTS MALADES   (France)

Author keywords

CYP2D6; Cytochrome P450; N hydroxylation; Procainamide

Indexed keywords

CYTOCHROME P450; FURAFYLLINE; KETOCONAZOLE; NITROSO DERIVATIVE; PROCAINAMIDE; QUINIDINE; SULFAPHENAZOLE;

ARTICLE; CONTROLLED STUDY; DRUG HYDROXYLATION; DRUG METABOLISM; ENZYME ACTIVITY; GENE TRANSFER; HUMAN; HUMAN TISSUE; IN VITRO STUDY; LIVER MICROSOME; LUPUS ERYTHEMATOSUS; LYMPHOBLASTOID CELL; METABOLITE; NITROSATION; PRIORITY JOURNAL; PROTEIN EXPRESSION; YEAST;

ANTI-ARRHYTHMIA AGENTS; CELLS, CULTURED; CYTOCHROME P-450 CYP2D6; HUMANS; HYDROXYLATION; MICROSOMES, LIVER; PROCAINAMIDE; RECOMBINANT PROTEINS; SACCHAROMYCES CEREVISIAE;

EID: 0030868486     PISSN: 0960314X     EISSN: None     Source Type: Journal    
DOI: 10.1097/00008571-199710000-00007     Document Type: Article

References (49)

1. Alarcon-Segovia D. Drug-induced antinuclear antibodies and lupus syndromes. Drugs 1976: 12, 69-77.
2. Bélanger PM, Grech-Bélanger O, Blouin M. Colorimetric determination of N-hydroxylated metabolites in microsomal studies. Anal Biochem 1981: 118, 47-52.
3. Bigger JT, Jr, Heissenbuttel RH. The use of procainamide and lidocaine in the treatment of cardiac arrhythmias. Prog Cardiovasc Dis 1969: 11, 515-534.
4. Blomgren SE, Condeme JJ, Bignall MC, Vaughan JH. Antinuclear antibody induced by procainamide: a prospective study. N Engl J Med 1969: 281, 64-66.
5. Budinsky RA, Roberts SM, Coats EA, Adams L, Hess EV. The formation of procainamide hydroxylamine by rat and human liver microsomes. Drug Metab Disp 1987: 15, 37-43.
6. Ching MS, Blake CL, Ghabrial H, Ellis SW, Lennard MS, Tucker GT, Smallwood RA. Potent inhibition of yeast-expressed CYP2D6 by dihydroquinidine, quinidine, and its metabolites. Biochem Pharmacol 1995: 50, 833-837.
7. Christoff PB, Conti DR, Naylor C, Jusko WJ. Procainamide disposition in obesity. Drug Intel Clin Pharm 1983: 17, 516-522.
8. Coyle JD, Boudoulas H, MacKichan JJ, Lima JJ. Concentration-dependent clearance of procainamide in normal subjects. Biopharm Drug Disp 1985: 6, 159-165.
9. de Groot MJ, Vermeulen NPE, Kramer JD, van Acker FAA, Donné-Op den Kelder GM. A three-dimensional protein model for human cytochrome P450 2D6 based on the crystal structures of P450 101, P450 102, and P450 108. Client Res Toxicol 1996: 9, 1079-1091.
10. de Groot MJ, Bijloo GJ, Martens BJ, van Acker FAA, Vermeulen NPE. A refined substrate model for human cytochrome P450 2D6. Chem Res Toxicol 1997: 10, 41-48.
11. DuSouich P, Erill S. Patterns of acetylation of procainamide and procainamide derived p-aminobenzoic acid in man. European Journal of Clinical Investigation 1976: 10, 283-287.
12. Eichelbaum M, Gross AS. The genetic polymorphism of debrisoquine/sparteine metabolism. Clinical aspects. Pharmacol Ther 1990: 46, 377-394.
13. Ellis SW, Hayhurst GP, Smith G, Lightfoot T, Wong MMS, Simula AP, Ackland MJ, Sternberg MJE, Lennard MS, Tucker GT, Wolf CR. Evidence that aspartic acid 301 is a critical substrate-contact residue in the active site of cytochrome P450 2D6. J Biol Chem 1995: 270, 29055-29058.
14. Freeman RW, Woosley RL, Oates JA, Harbison RL. Evidence for the biotransformation of procainamide to a reactive metabolite. Toxicol Appl Pharmacol 1979: 50, 9-16.
15. Freeman RW, Uetrecht JP, Woosley RL, Oates JA, Harbison RD. Covalent binding of procainamide in vitro and in vivo to hepatic protein in mice. Drug Metab Disp 1981: 9, 188-192.
16. Frislid K, Berg M, Hansteen V. Comparison of the acetylation of procainamide and sulfamidine in man. Eur J Clin Invest 1976: 9, 433-438.
17. Gibson TP, Matusik J, Matusik E. Acetylation of procainamide in man and its relationship to isonicotinic acid hydrazide acetylation phenotype. Clin Pharmacol Ther 1974: 17, 395-399.
18. Gibson TP, Atkinson AJ, Jr, Matusik E. Kinetics of procainamide and N-acetylprocainamide in renal failure. Kidney Int 1977: 12, 422-429.
19. Griesemer DA. Procainamide-induced lupus. Johns Hopkins Med J 1976: 138, 289-295.
20. Henningsen NC, Cederberg A, Hanson A, Johansson BW. Effects of long-term treatment with procaine amide. Acta Med Scand 1975: 198, 475-482.
21. Interian A, Jr, Zaman L, Velez-Robinson E, Kozlovskis P, Castellanos A, Myerburg RJ. Paired comparisons of efficacy of intravenous and oral procainamide in patients with inducible sustained ventricular tachyarrhythmias. J Am Coll Cardiol 1991: 17, 1581-1586.
22. Islam SA, Wolf CR, Lennard MS, Sternberg MJE. A three-dimensional molecular template for substrates of human cytochrome P450 involved in debrisoquine 4-hydroxylation. Carcinogenesis 1991: 12, 2211-2219.
23. Jiang X, Khursigara G, Rubin RL. Transformation of lupus-inducing drugs to cytotoxic products by activated neutrophils. Science 1994: 266, 810-813.
24. Karlsson E, Molin L. Polymorphic acetylation of procainamide in healthy subjects. Acta Med Scand 1975: 197, 299-302.
25. Koch-Weser J. Pharmacokinetics of procainamide in man. Ann NY Acad Sci 1971: 179, 370-382.
26. Koch-Weser J. Antiarrhythmic prophylaxis in ambulatory patients with coronary heart disease. Arch Intern Med 1972: 129, 763-772.
27. Koymans L, Vermeulen NPE, van Acker SABE, te Koppele JM, Heykants JJP, Lavrijsen K, Meuldermans W, Donné-Op den Kelder GM. A predictive model for substrates of cytochrome P450-debrisoquine (2D6). Chem Res Toxicol 1992: 5, 211-219.
28. Meyer UA, Gut J, Kronbach T, Skoda C, Meir UT, Catin T, Dayer P. The molecular mechanisms of two common polymorphisms of drug oxidation - evidence for functional changes in cytochrome P-450 isozymes catalysing bufuralol and mephenytoin oxidation. Xenobiotica 1986: 16, 449-464.
29. 150 2D6 based on homology modeling and NMR studies of substrate binding. Biochem 1996: 35, 4540-4550.
30. Mongey AB, Donovan-Brand R, Thomas T, Adams LE, Hess EV. Serologic evaluation of patients receiving procainamide. Arthritis Rheum 1992: 35, 219-223.
31. Okumura K, Kita T, Chikazawa S, Komada F, Iwakawa S, Tanigawara Y. Genotyping of N-acetylation polymorphism and correlation with procainamide metabolism. Clin Pharmacol Ther 1997: 61, 509-517.
32. Otton SV, Crewe HK, Lennard MS, Tucker GT, Woods HF. Use of quinidine inhibition to define the role of the sparteine/debrisoquine cytochrome P450 in metoprolol oxidation by human liver microsomes. J Pharmacol Exp Ther 1988a: 247, 242-247.
33. Otton SV, Lennard MS, Tucker GT, Woods HF. Effect of quinidine and quinine on metoprolol oxidation in human liver microsomes. Br J Clin Pharmacol 1988b: 26, 644P.
34. Reidenberg MM, Drayer DE, Levy M, Warner H. Polymorphic acetylation of procainamide in man. Clin Pharmacol Ther 1975: 172, 722-730.
35. Roberts SM, Adams LE, Donovan-Brand RJ, Budinsky RA, Skoulis NP, Zimmer HW, Hess EV. Procainamide hydroxylamine lymphocyte toxicity in the rat: evidence for participation by hemoglobin. Int J Pharmac 1989: 11, 419-427.
36. Roden DM, Reele SB, Higgins SB, Wilkinson GR, Smith R, Oates JA, Woosley RL. Antiarrhythmic efficacy, pharmacokinetics and safety of N-acetylprocainamide in human subjects: comparison with procainamide. Am J Cardiol 1980: 46, 463-68.
37. Smith DA, Jones BC. Speculations on the substrate structure-activity relationship (SSAR) of cytochrome P450 enzymes. Biochem Pharmacol 1992: 44, 2089-2098.
38. Strobl G, Heinrich B, Wolff T, Guengerich FP. Inhibition of bufuralol-1 hydroxylation in rat and human liver: In vitro studies and inhibitor modelling. In: Schuster I, ed. Cytochrome P-450: Biochemistry and biophysics. London: Taylor and Francis, 1989: 407-410.
39. Uetrecht J. Drug metabolism by leukocytes and its role in drug-induced lupus and other idiosyncratic drug reactions. Toxicology 1990: 20, 213-235.
40. Uetrecht JP, Woosley RL. Acetylator phenotype and lupus erythematosus. Clin Pharmacokinet 1981: 6, 118-134.
41. Uetrecht JP, Freeman RW, Woosley RL. The implications of procainamide metabolism to its induction of lupus. Arthritis Rheum 1981: 24, 994-999.
42. Uetrecht JP, Sweetman BJ, Woosley RL, Oates JA. Metabolism of procainamide to a hydroxylamine by rat and human hepatic microsomes. Drug Metab Disp 1984: 12, 77-81.
43. Uetrecht JP, Zahid N, Rubin RL. Metabolism of procainamide to a hydroxylamine by human neutrophils and mononuclear leukocytes. Chem Res Toxicol 1988: 1, 74-78.
44. Uetrecht J, Zahid N, N-chlorination and oxidation of procainamide by myeloperoxidase: toxicological implications. Chem Res Toxicol 1991: 4, 218-222.
45. von Schmiedeberg S, Goebel C, Gleichmann E, Uetrecht J. Neutrophils and drug metabolism. Science 1995: 268, 585-586.
46. Weinstein A. Drug-induced lupus erythematosus. Progress in Clinical Immunology 1980: 4, 1-21.
47. Wolff T, Distlerath LM, Worthington MT, Groopman JD, Hammons GJ, Kadlubar FF, Prough RA, Martin MV, Guengerich FP. Substrate specificity of human liver cytochrome P-450 debrisoquine 4-hydroxylase probed using immunochemical inhibition and chemical modeling. Cancer Res 1985: 45, 2116-2122.
48. Wolff T, Distlerath LM, Worthington MT, Guengerich FP. Human liver debrisoquine 4-hydroxylase: test for specifity toward various monooxygenase substrates and model of the active site. Arch Toxicol 1987: 60, 89-90.
49. Woosley RL, Drayer DE, Reidenberg MM, Nies AS. Effect of acetylator phenotype on the rate at which procainamide induces antinuclear antibodies and the lupus syndrome. N Engl J Med 1978: 298, 1157-1159.