N-dealkylation of arylpiperazine derivatives: Disposition and metabolism of the 1-aryl-piperazines formed

Current Drug Metabolism

Volumn 8, Issue 6, 2007, Pages 612-622

  Caccia, Silvio ^a  

^a MARIO NEGRI INSTITUTE FOR PHARMACOLOGICAL RESEARCH   (Italy)

Author keywords

1 aryl piperazines; Arylpiperazine derivatives; CYP2D6 dependent metabolism; CYP3A4 dependent N dealkylation; Disposition

Indexed keywords

(3 CHLOROPHENYL)PIPERAZINE; 1 ARYLPIPERAZINE DERIVATIVE; ARIPIPRAZOLE; ARYLPIPERAZINE DERIVATIVE; BUSPIRONE; CARBAMAZEPINE; CYTOCHROME P450 2D6; CYTOCHROME P450 3A4; DERAMCICLANE FUMARATE; DRUG METABOLIZING ENZYME; ENCIPRAZINE; ETOPERIDONE; FLUOXETINE; GEPIRONE; HALOPERIDOL; HYDROXYNEFAZODONE; IPSAPIRONE; ITRACONAZOLE; KETOCONAZOLE; NEFAZODONE; PEROSPIRONE; PIPERAZINE DERIVATIVE; PLACEBO; RIFAMPICIN; TANDOSPIRONE; THIORIDAZINE; TIOSPIRONE; TRAZODONE; UNCLASSIFIED DRUG; UNINDEXED DRUG; ZIPRASIDONE;

AREA UNDER THE CURVE; CLINICAL TRIAL; DEPRESSION; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG BRAIN LEVEL; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG ELIMINATION; DRUG HALF LIFE; DRUG METABOLISM; DRUG POTENTIATION; DRUG PROTEIN BINDING; DRUG STRUCTURE; ENZYME ACTIVITY; HUMAN; HYDROPHOBICITY; LIVER TOXICITY; NONHUMAN; REPEATED DRUG DOSE; REVIEW; SCHIZOPHRENIA; TRANQUILIZING ACTIVITY;

ANIMALS; DEALKYLATION; HUMANS; PIPERAZINES; TISSUE DISTRIBUTION;

EID: 34547672814     PISSN: 13892002     EISSN: None     Source Type: Journal    
DOI: 10.2174/138920007781368908     Document Type: Review

References (97)

1. Murphy, D.L.; Lesch, K.P.; Aulakh, C.S.; Pigott, T.A. (1991) Pharmacol. Rev., 43(4), 527-552.
2. Gommans, J.; Hijzen, T.H.; Maes, R.A.; Olivier, B. (1998) Psychopharmacology (Berl), 137(3), 292-302.
3. Gatch, M.B. (2003) Life Sci., 73(11), 1347-67.
4. Baumann, M.H.; Rutter, J.J.; Auerbach, S.B. (1993) Neuropharmacology, 32(12), 1381-1386.
5. Baumann, M.H.; Mash, D.C.; Staley, J.K. (1995) Neuroreport, 6(16), 2150-2152.
6. Thomas, D.R.; Gager, T.L.; Holland, V.; Brown, A.M.; Wood, M.D (1996) Neuroreport, 7(9), 1457-1460.
7. Wood, M.; Chaubey, M.; Atkinson, P.; Thomas, D.R. (2000) Eur. J. Pharmacol., 396(1), 1-8.
8. Saari, W.S.; Halczenko, W.; King, S.W.; Huff, J.R.; Guare, J.P. Jr.; Hunt, C.A.; Randall, W.C.; Anderson, P.S.; Lotti, V.J.; Taylor, D.A.; Clineschmidt, B.V. (1983) J. Med. Chem., 26(12), 1696-1701.
9. Gobbi, M.; Frittoli, E.; Mennini, T. (1990) Eur. J. Pharmacol., 180(1), 183-186.
10. Blier, P.; Curet, O.; Caput, Y.; de Montigny, C. (1991) Neuropharmacology, 30(7), 691-701.
11. Berlin, I.; Chalon, S.; Payan, C.; Schollnhammer, G.; Cesselin, F.; Varoquaux, O.; Puech, A.J. (1995) Br. J. Clin Pharmacol., 39(3), 243-249.
12. Kahn, R.S.; Wetzler, S. (1991) Biol. Psychiatry, 30(11), 1139-1166.
13. Caccia, S. (1990) Boll. Chim. Farm., 129(5), 183-189.
14. Caccia, S.; Garattini, S. (1990) Acta Pharm. Jugosl., 40, 441-460.
15. de Boer, D.; Bosman, I.J.; Hidvegi, E.; Manzoni, C.; Benko, A.A.; dos Reys, L.J.; Maes, R.A. (2001) Forensic Sci. Int., 121(1-2), 47-56.
16. Staack, R.F.; Maurer, H.H. (2005) Curr. Drug Metab., 6(3), 259-274.
17. Eison, A.S. (1990) J. Clin. Psychopharmacol., (3 Suppl),2S-5S.
18. Blier, P.; Ward, N.M. (2003) Biol. Psychiatry, 53(3),193-203.
19. Mahmood, I.; Sahajwalla, C. (1999) Clin. Pharmacokinet., 36(4),277-87.
20. Swainston Harrison, T.; Perry, C.M. (2004) Drugs, 64(15),1715-1736.
21. Miao, Z.; Kamel, A.; Prakash, C. (2005) Drug Metab. Dispos., 33(7),879-883.
22. Beedham, C.; Miceli, J.J.; Obach, R.S. (2003) J. Clin. Psychopharmacol., 23(3), 229-232.
23. Food and Drug Administration Center for Drug Evaluation and Research. (2006) In Application No. 21-436. http://www.fda.gov/cder/foi/nda/ 2002/21-436_Abilify.htm
24. Lawler, C.P.; Prioleau, C.; Lewis, M.M.; Mak, C.; Jiang, D.; Schetz, J.A.; Gonzalez, A.M.; Sibley, D.R.; Mailman, R.B. (1999) Neuropsychopharmacology, 20(6), 612-627.
25. Wood, M.D.; Scott, C.; Clarke, K.; Westaway, J.; Davies, C.H.; Reavill, C.; Hill, M.; Rourke, C.; Newson, M.; Jones, D.N.; Forbes, I.T.; Gribble, A. (2006) Eur. J. Pharmacol., 546(1-3),88-94.
26. Testa, B. (1995) in The Metabolism of Drugs and Other Xenobiotics, (Testa, B.; Caldwell, J. Eds.) Academic Press, New York, pp. 203-234.
27. Mayol, R.F.; Cole, C.A.; Luke, GM.; Colson, K.L.; Kerns, E.H. (1994) Drug Metab. Dispos., 22(2),304-311.
28. Caccia, S.; Garattini, S. (1990) Clin. Pharmacokinet., 18(6), 434-459.
29. Caldwell, G.W.; Wu, W.N.; Masucci, J.A. (2001) Xenobiotica, 31(11), 823-839.
30. Colovic, M.; Campiani, G.; Butini, S.; Parabiaghi, A.; Caccia, S. (2006) Pharmacologyonline, 2, 252-260.
31. Prakash, C.; Kamel, A.; Gummerus, J.; Wilner, K. (1997) Drug Metab. Dispos., 25(7), 863-872.
32. Caccia, S. (2004) IDrugs, 7(2),143-150.
33. Cao, B.J.; Rodgers, R.J. (1997) Neuropharmacology, 36(8),1089-1097.
34. Zuideveld, K.P.; Rusic-Pavletic, J.; Maas, H.J.; Peletier L.A.; Van der Graaf, P.H.; Danhof, M. (2002) J. Pharmacol. Exp. Ther., 303(3), 1130-1137.
35. Vaidya, A.H.; Rosenthal, D.I.; Lang, W.; Crooke, J.J.; Benjamin, D.; Ilyin, S.E.; Reitz, A.B. (2005) Methods Find Exp Clin. Pharmacol., 27(4), 245-255.
36. Nishitsuji, K.; To, H.; Shimizu, T.; Yanase, Y.;Yamada,T.; Hara, C.; Mine, K.; Higuchi, S. (2006) Eur. Neuropsychopharmacol., 16(5), 376-382.
37. Lucki, I. (1991) J. Clin. Psychiatry, 52 Suppl., 24-31.
38. Redrobe, J.P.; Bourin, M. (1998) Psychopharmacology (Berl.), 138(2), 198-206.
39. Mayol, R.F.; Jajoo, H.K.; Klunk, L.J.; Blair, I.A. (1991) Drug Metab. Dispos.,19(2), 394-399.
40. Mizuno, Y.; Tani, N.; Komuro, S.; Kanamaru, H.; Nakatsuka,I. (2003) Eur. J. Drug Metab. Pharmacokinet., 28(1), 59-65.
41. Caccia, S. (2000) Clin. Pharmacokinet., 38(5), 393-414.
42. Zhu, M.; Zhao, W.; Jimenez, H.; Zhang, D.; Yeola, S.; Dai, R.; Vachharajani, N.; Mitroka, J. (2005) Drug Metab. Dispos., 33(4), 500-507.
43. von Moltke, L.L.; Greenblatt, D.J.; Grassi, J.M.; Granda, B.W.; Fogelman, S.M.; Harmatz, J.S.; Kramer, S.J.; Fabre, L.F.; Shader, R.I. (1998) Psychopharmacology (Berl.), 140(3), 293-299.
44. Greenblatt, D.J.; Von Moltke, L.L.; Giancarlo, G.M.; Garteiz, D.A. (2003) Biopharm. Drug Dispos., 24(2), 87-94.
45. Yan, Z.; Caldwell, G.W.; Wu, W.N.; McKown, L.A.; Rafferty, B.; Jones, W.; Masucci, J.A. (2002) Xenobiotica, 32(11), 949-962.
46. von Moltke, L.L.; Greenblatt, D.J.; Granda, B.W.; Grassi, J.M.; Schmider, J.; Harmatz, J.S.; Shader, R.I. (1999) Psychopharmacology (Berl.),145(1), 113-122.
47. Rotzinger, S.; Baker, G.B. (2002) Eur. Neuropsychopharmacol., 12(2), 91-100.
48. Rotzinger, S.; Fang, J.; Baker, G.B. (1998) Drug Metab. Dispos., 26(6), 572-575.
49. Zalma, A.; von Moltke, L.L.; Granda, B.W.; Harmatz, J.S.; Shader, R.I.; Greenblatt, D.J. (2000) Biol. Psychiatry, 47(7), 655-661.
50. Shimakura, J.; Tani, N.; Mizuno, Y.; Komuro, S.; Kanamaru, H. (2003) Eur. J. Drug Metab. Pharmacokinet., 28(1), 67-72.
51. Prakash, C.; Kamel, A.; Cui, D.; Whalen, RD.; Miceli, J.J.; Tweedie, D. (2000) Br. J. Clin. Pharmacol., 49(Suppl 1), 35S-42S.
52. Zhou, S.; Chan, E.; Lim, L.Y.; Boelsterli, U.A.; Li, S.C.; Wang, J.; Zhang, Q.; Huang M.; Xu, A. (2004) Curr. Drug Metab., 5(5), 415-442.
53. Luo, G.; Guenthner, T.; Gan, L.S.; Humphreys,W.G. (2004) Curr. Drug Metab., 5(6), 483-505.
54. Otani, K.; Ishida, M.; Kaneko, S.; Mihara, K.; Ohkubo, T.; Osanai, T.; Sugawara, K. (1996) Ther. Drug Monit., 18(2),164-167.
55. Laroudie, C.; Salazar, D.E.; Cosson, J.P.; Cheuvart, B.; Istin, B.; Girault, J.; Ingrand, I.; Decourt, J.P. (2000) J. Clin. Psychopharmacol., 20(1), 46-53.
56. Feuchtl, A.; Bagli, M.; Stephan, R.; Frahnert, C.; Kolsch, H.; Kuhn, K.U.; Rao, M.L.; (2004) Pharmacopsychiatry, 37(4),180-188.
57. Greene, D.S.; Barbhaiya, R.H. (1997) Clin. Pharmacokinet., 33(4), 260-275.
58. Nilsen, O.G.; Dale, O. (1992) Pharmacol. Toxicol., 71(2),150-153.
59. Trazodone (1994) in Therapeutic Drugs, (Dollery, C. Ed.), Churchill, Livingstone, London, pp. 115-118.
60. Miller, L.G.; Thompson, M.L.; Byrnes, J.J.; Greenblatt, D.J.; Shemer, A. (1992) J. Clin. Psychopharmacol., 12(5), 341-345.
61. Bossong, M.G.; Van Dijk, J.P.; Niesink, R.J. (2005) Addict. Biol., 10(4), 321-323.
62. Nacca, A.; Guiso, G.; Fracasso, C.; Cervo, L.; Caccia, S. (1998) Br. J. Pharmacol., 125(7),1617-1623.
63. Benjamin, J.; Greenberg, B.D.; Murphy, D.L. (1996) Psychopharmacology (Berl.), 127(2), 140-149.
64. Scatina, J.A.; Lockhead, S.R.; Cayen, M.N.; Sisenwine, S.F. (1991) Xenobiotica, 21(12), 1591-604.
65. Tsutsumi, H.; Katagi, M.; Miki, A.; Shima, N.; Kamata, T.; Nakajima, K.; Inoue, H.; Kishi, T.; Tsuchihashi, H. (2005) Xenobiotica, 35(1), 107-116.
66. Mayol, R.F.; Cole, C.A.; Colson, K.E.; Kerns, E.H. (1994) Drug Metab. Dispos., 22(1), 171-174.
67. Caliendo, G.; Santagada, V.; Perissutti, E.; Fiorino, F. (2005) Curr. Med. Chem.,12(15), 1721-1753.
68. Cervo, L.; Burbassi, S.; Colovic, M.; Caccia, S. (2005) Pharmacol. Biochem. Behav., 82(4), 727-734.
69. Ma, Y.; Kiesewetter, D.; Lang, L.; Eckelman,W.C. (2003) Mol. Imaging Biol., 5(6), 397-403.
70. Raghavan, N.; Zhang, D.; Zhu, M.; Zeng, J.; Christopher L. (2005) Drug Metab. Dispos., 33(2), 203-208.
71. Rotzinger, S.; Fang, J.; Coutts, R.T.; Baker, G.B. (1998) Biol. Psychiatry, 44(11), 1185-1191.
72. Staack, R.F.; Paul, L.D.; Springer, D.; Kraemer, T.; Maurer, H.H. (2004) Biochem. Pharmacol., 15; 67(2), 235-244.
73. Findling, R.L.; Preskorn, S.H.; Marcus, R.N.; Magnus, R.D.; D'Amico, F.; Marathe, P.; Reed, M.D. (2000) J. Am. Acad. Child Adolesc. Psychiatry, 39(8), 1008-1016.
74. Yasui, N.; Otani, K.; Kaneko, S.; Ohkubo, T.; Osanai, T.; Ishida, M.; Mihara, K.; Kondo, T.; Sugawara, K.; Fukushima, Y. (1995) Ther. Drug Monit., 17(4), 333-335.
75. Mihara, K.; Otani, K.; Ishida, M.; Yasui, N.; Suzuki, A.; Ohkubo, T.; Osanai, T.; Kaneko, S.; Sugawara, K. (1997) Ther. Drug Monit., 19(1), 43-45.
76. Maes, M.; Westenberg, H.; Vandoolaeghe, E.; Demedts, P.; Wauters, A.; Neels, H.; Meltzer, HY. (1997) J. Clin. Psychopharmacol., 17(5), 358-364.
77. Otani, K.; Tybring, G.; Mihara, K.; Yasui, N.; Kaneko, S.; Ohkubo, T.; Nagasaki, T.; Sugawara, K. (1998) Eur. J. Clin. Pharmacol., 53(5), 347-349.
78. Laine, K.; De Bruyn, S.; Bjorklund, H.; Rouru, J.; Hanninen, J.; Scheinin, H.; Anttila, M. (2004) Eur. J. Clin. Pharmacol., 59(12), 893-898.
79. Laine, K.; Ahokoski, O.; Huupponen, R.; Hanninen, J.; Palovaara, S.; Ruuskanen, J.; Bjorklund, H.; Anttila, M.; Rouru, J. (2003) Eur. J. Clin. Pharmacol., 59(10), 761-766.
80. Gijsman, H.J.; Cohen, A.F.; van Gerven, J.M. (2004) J. Psychopharmacol., 18(1), 7-13.
81. Sakr, A.; Andheria, M. (2001) J. Clin. Pharmacol., 41(7), 783-789.
82. Timmer, C.J.; Sitsen, J.M. (2003) J. Pharm. Sci., 92(9), 1773-1778.
83. Sakr, A.; Andheria, M.J. (2001) J. Clin. Pharmacol., 41(8), 886-894.
84. Tay, L.K.; Sciocca, M.A.; Sostrin, M.B.; Farmen, R.H.; Pittman, K.A. (1993). J. Clin. Pharmacol., 33, 631-635.
85. Gunasekara, N.S.; Spencer, C.M.; Keating, G.M. (2002) Drugs, 62(8), 1217-1251.
86. Preskorn, S.H. (2005) Clin. Pharmacokinet., 44(11), 1117-1133.
87. DeLeon, A.; Patel, N.C.; Crismon, M.L. (2004) Clin. Ther., 26(5), 649-666.
88. Preskorn, S.H. (1993) J. Clin. Psychiatry, 54 Suppl, 14-34.
89. Ishida, M.; Otani, K.; Kaneko, S.; Ohkubo, T.; Osanai,T.; Yasui, N.; Mihara, K.; Higuch, H.; Sugawara, K. (1995) Int. Clin. Psychopharmacol., 10(3), 143-146.
90. Otani, K.; Mihara, K.; Yasui, N.; Ishida, M.; Kondo, T.; Tokinaga, N.; Ohkubo, T.; Osanai, T.; Sugawara, K.; Kaneko, S. (1997) Prog. Neuropsychopharmacol. Biol. Psychiatry, 21(1), 239-244.
91. Monteleone, P.; Gnocchi, G. (1990) Clin. Neuropharmacol., 13 (Suppl 1), S84-S89.
92. Mihara, K.; Yasui-Furukori, N.; Kondo, T.; Ishida, M.; Ono, S.; Ohkubo, T.; Osanai, T.; Sugawara, K.; Otani, K.; Kaneko, S. (2002) Ther. Drug Monit., 24(4), 563-566.
93. von Moltke, L.L.; Greenblatt, D.J.; Shader, R.I. (1993) Clin. Pharmacokinet., 24(2), 141-160.
94. Salazar, D.E.; Frackiewicz, E.J.; Dockens, R.; Kollia, G.; Fulmor, I.E.; Tigel, P.D.; Uderman, H.D.; Shiovitz, T.M.; Sramek, J.J.; Cutler, N.R. (2001) J. Clin. Pharmacol., 41(12), 1351-1358.
95. Edwards, D.J.; Chugani, D.C.; Chugani, H.T.; Chehab, J.; Malian, M.; Aranda, J.V. (2006) J. Clin. Pharmacol., 46(5), 508-514.
96. Villeneuve, J.P.; Pichette, V. (2004) Curr. Drug Metab., 5(3), 273-282.
97. Obach, R.S.; Walsky, R.L. (2005) J. Clin. Psychopharmacol., 25(6), 605-608.