Bioactivation and hepatotoxicity of nitroaromatic drugs

Current Drug Metabolism

Volumn 7, Issue 7, 2006, Pages 715-727

  Boelsterli, Urs A ^a   Ho, Han Kiat ^b   Zhou, Shufeng ^a   Leow, Koon Yeow ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b AGENCY FOR SCIENCE   (Singapore)

Author keywords

Drug induced liver injury; Flutamide; Hepatotoxicity; Mitochondria; Nimesulide; Nitroarene; Nitroreduction; Tolcapone

Indexed keywords

ALDEHYDE OXIDASE; AROMATIC NITRO COMPOUND; BENZNIDAZOLE; BICALUTAMIDE; DANTROLENE; ENDOTHELIAL NITRIC OXIDE SYNTHASE; ENTACAPONE; FLUTAMIDE; INDUCIBLE NITRIC OXIDE SYNTHASE; MISONIDAZOLE; NEURONAL NITRIC OXIDE SYNTHASE; NIFEDIPINE; NIFUROXIME; NIFURTIMOX; NILUTAMIDE; NIMESULIDE; NITROFURAL; NITROFURANTOIN; ORNIDAZOLE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE (QUINONE); REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE FERRIHEMOPROTEIN REDUCTASE; RONIDAZOLE; TOLCAPONE; XANTHINE OXIDASE;

AREA UNDER THE CURVE; CHOLESTASIS; COVALENT BOND; DISORDERS OF MITOCHONDRIAL FUNCTIONS; DOSE RESPONSE; DRUG ACTIVATION; DRUG HALF LIFE; DRUG MEGADOSE; DRUG METABOLISM; DRUG OXIDATION; DRUG POTENCY; DRUG STRUCTURE; DRUG TOLERABILITY; ELECTRON TRANSPORT; ENZYME ACTIVITY; HUMAN; LIVER FAILURE; LIVER INJURY; LIVER NECROSIS; LIVER TOXICITY; LUNG FIBROSIS; LUNG TOXICITY; MITOCHONDRIAL TOXICITY; NONHUMAN; OXIDATIVE STRESS; PATHOGENESIS; PROSTATE CARCINOMA; REDUCTION; REVIEW; STRUCTURE ACTIVITY RELATION;

BENZOPHENONES; BIOTRANSFORMATION; DRUG-INDUCED LIVER INJURY; FLUTAMIDE; HEPATITIS, TOXIC; IMIDAZOLIDINES; NIFEDIPINE; NITRO COMPOUNDS; NITROFURANTOIN; NITROPHENOLS; SULFONAMIDES;

EID: 33749437211     PISSN: 13892002     EISSN: None     Source Type: Journal    
DOI: 10.2174/138920006778520606     Document Type: Review

References (113)

1. Purohit, V. and Basu, A. K. (2000) Chem. Res. Toxicol., 13(8), 673-692.
2. Ritter, C. L. and Malejka-Giganti, D. (1998) Chem. Res. Toxicol., 11(11), 1361-1367.
3. Nelson, S. D. (2001) Adv. Exp. Med. Biol., 500, 33-43.
4. Williams, D. P. and Naisbitt, D. J. (2002) Curr. Opin. Drug Discov. Develop., 5(1), 104-115.
5. Soojhawon, I.; Lokhande, P.D.; Kodam, K.M. and Gawai, K.R. (2005) Enzyme Microb. Technol., 37, 527-533.
6. Biaglow, J.E.; Varnes, M.E.; Roizen-Towle, L.; Clark, E.P.; Epp, E.R.; Astor, M.B. and Hall, E.J. (1986) Biochem. Pharmacol., 35(1), 77-90.
7. Rickert, D.E. (1987) Drug Metab. Rev., 18(1), 23-53.
8. Kedderis, G.L. and Miwa, G.T. (1988) Drug Metab. Rev., 19(1), 33-62.
9. Kedderis, G.L.; Argenbright, L.S. and Miwa, G.T. (1989) Chem. Res. Toxicol., 2(3), 146-149.
10. Mason, R.P. and Holtzman, J.L. (1975) Biochemistry, 14(8), 1626-1632.
11. Fau, D.; Berson, A.; Eugene, D.; Fromenty, B.; Fisch, C. and Pessayre, D. (1992) J. Pharmacol. Exp. Ther., 263(1), 69-77.
12. Lewis, J.H.; Zimmerman, H.J. (1999) Clin. Liver Dis., 3(3): 433-64
13. Orna, M.V. and Mason, R.P. (1989) J. Biol. Chem., 264(21), 12379-12384.
14. Cenas, N.; Nemaikaite-Ceniene, A.; Sergediene, E.; Nivinskas, H.; Anusevicius, Z. and Sarlauskas, J. (2001) Biochim. Biophys. Acta, 1528(1), 31-38.
15. Berson, A.; Wolf, C.; Chachaty, C.; Fisch, C.; Fau, D.; Eugene, D.; Loeper, J.; Gauthier, J.C.; Beaune, P.H.; Pompon, D.; Maurel, P. and Pessayre, D. (1993) J. Pharmacol. Exp. Ther., 265(1), 366-372.
16. Rao, D.N.R.; Jordan, S. and Mason, R.P. (1988) Biochem. Pharmacol., 37(15), 2907-2913.
17. Berson, A.; Wolf, C.; Berger, V.; Fau, D.; Chachaty, C.; Fromenty, B. and Pessayre, D. (1991) J. Pharmacol. Exp. Ther., 257(2), 714-719.
18. Kim, D.; Kadlubar, F.F.; Teitel, C.H. and Guengerich, F.P. (2004) Chem. Res. Toxicol., 17(4), 529-536.
19. Jones, C.R. and Sabbioni, G. (2003) Chem. Res. Toxicol., 16(10), 1251-1263.
20. Svensson, C.K. (2003) Chem. Res. Toxicol., 16(9), 1035-1043.
21. Cribb, A.E.; Miller, M.; Leeder, J.S.; Hill, J. and Spielberg, S.P. (1991) Drug Metab. Dispos., 19(5), 900-906.
22. Naisbitt, D.J.; Hough, S.J.; Gill, H.J.; Pirmohamed, M.; Kitteringham, N.R. and Park, B.K. (1999) Br. J. Pharmacol., 126(6), 1393-1407.
23. Ask, K.; Decologne, N.; Asare, N.; Holme, J.A.; Artur, Y.; Pelczar, H. and Camus, P. (2004) Toxicol. Appl. Pharmacol, 201(1), 1-9.
24. Ueda, O.; Sugihara, K.; Ohta, S. and Kitamura, S. (2005) Drug Metab. Dispos., 33(9), 1312-1318.
25. Arlt, V.M.; Stiborova, M.; Hewer, A.; Schmeiser, H.H. and Phillips, D.H. (2003) Cancer Res., 63(11), 2752-2761.
26. Ask, K.; Dijols, S.; Giroud, C.; Casse, L.; Frappart, Y.M.; Sari, M.A.; Kim, K.S.; Stuehr, D.J.; Mansuy, D.; Camus, P. and Boucher J.L. (2003) Chem. Res. Toxicol., 16(12), 1547-1554.
27. Elfering, S.L.; Sarkela, T.M. and Giulivi, C. (2002) J. Biol. Chem., 277(41), 38079-38086.
28. Ask, K.; Decologne, N.; Ginies, C.; Lag, M.; Boucher, J.L.; Holme, J.A.; Pelczar, H. and Camus, P. (2006) Biochem. Pharmacol., 71(3), 377-385.
29. Bredt, D.S.; Hwang, P.M.; Glatt, C.E.; Lowenstein, C.; Reed, R.R. and Snyder, S.H. (1991) Nature, 351(6329), 714-718.
30. Ghafourifar, P. and Cadenas, E. (2005) Trends Pharmacol. Sci., 26(4), 190-195.
31. Mingatto, F.E.; Rodrigues, T.; Pigoso, A.A.; Uyemura, S.A.; Curti, C. and Santos, A.C. (2002) J. Pharmacol. Exp. Ther., 303(2), 601-607.
32. Walsh, J.S.; Wang, R.; Bagan, E.; Wang, C.C.; Wislocki, P. and Miwa, G.T. (1987) J. Med. Chem., 30(1), 150-156.
33. Kalgutkar, A.S.; Gardner, I.; Obach, R.S.; Shaffer, C.L.; Callegari, E.; Henne K. R.; Mutlib, A.E.; Dalvie, D.K.; Lee, J.S.; Nakai, Y.; O'Donnell, J.P.; Boer, J. and Harriman,S.P. (2005) Curr. Drug Metab., 6(3), 161-225.
34. Mansuy, D.; Rouer, E.; Bacot, C.; Gans, P.; Chottard, J.C. and Leroux, J.P. (1978) Biochem. Pharmacol., 27(8), 1129-1137.
35. Uetrecht, J.P. (2000) Curr. Drug Metab., 1(2), 133-141.
36. Nuñez-Vergara, L.J.; Sturm, J.C.; Olea-Azar, C.; Nararrete-Encina, P.; Bollo, S. and Squella, J.A. (2000) Free Radic. Res., 32(5), 399-409.
37. Squella, J.A.; Gonzalez, P.; Bollo, S. and Nunez-Vergara, L.J. (1999) Pharm. Res., 16(1), 161-164.
38. Tay, V.K.S.; Wang, A.S.; Leow, K.Y.; Ong, M.M.K.; Wong, K.P. and Boelsterli, U.A. (2005) Free Radic. Biol. Med., 39(7), 949-959.
39. Nuñez-Vergara, L.J.; Farias, D.; Bollo, S. and Squella, J.A. (2001) Bioelectrochemistry, 53(1), 103-110.
40. Nunez-Vergara, L.J.; Navarrete-Encina, P.A.; Ortiz, M.E.; Bollo, S. and Squella, J.A. (1996) Chem.- Biol. Interact., 101(2), 89-101.
41. Rosen, G.M.; Demos, H.A. and Rauckman, E.J. (1984) Toxicol. Lett., 22(2), 145-152.
42. Fau, D.; Eugene, D.; Berson, A.; Letteron, P.; Fromenty, B.; Fisch, C. and Pessayre, D. (1994) J. Pharmacol. Exp. Ther., 269(3), 954-962.
43. Paterna, J.C.; Boess, F.; Stäubli, A. and Boelsterli, U.A. (1998) Toxicol. Appl. Pharmacol., 148(1), 117-125.
44. De Angelis, I.; Vincentini, O.; Brambilla, G.; Stammati, A. and Zucco, F. (1998) Toxicol. Appl. Pharmacol., 152(1), 119-127.
45. Letelier, M.E.; Izquierdo, P.; Godoy, L.; Lepe, A.M. and Faundez, M. (2004) J. Appl. Toxicol., 24(6), 519-525.
46. Ings, R.M.J.; McFadzean, J.A. and Ormerod, W.E. (1974) Biochem. Pharmacol., 23(9), 1421-1429.
47. Tereda, H. (1981) Biochim. Biophys. Acta, 639(3-4), 225-242.
48. Mingatto, F.E.; Cardozo dos Santos, A.; Rodrigues, T.; Pigoso, A.A.; Uyemura, S.A. and Curti, C. (2000) Br. J. Pharmacol., 131(6), 1154-1160.
49. Berson, A.; Schmets, L.; Fisch, C.; Fau, D.; Wolf, C.; Fromenty, B.; Deschamps, D. and Pessayre, D. (1994) J. Pharmacol. Exp. Ther, 270(1), 167-176.
50. Olanow, C.W. (2000) Arch. Neurol., 57(2), 263-267.
51. Spahr, L.; Rubbia-Brandt, L.; Burkhard, P.R.; Assal, F. and Hadengue, A. (2000) Dig. Dis. Sci., 45(9), 1881-1884.
52. Borges, N. (2003) Drug Safety, 26(11), 743-747.
53. Fisher, A.; Croft-Baker, J.; Davis, M.; Purcell, P. and McLean, A.J. (2002) Mov. Disord., 17(6), 1362-1365.
54. Haasio, K.; Sopanen, L.; Vaalavirta, L.; Linden, I.B. and Heinonen, E.H. (2001) J. Neural Transm., 108(1), 79-91.
55. Smith, K.S.; Smith, P.L.; Heady, T.N.; Trugman, J.M.; Harman, W.D. and Macdonald,T.L. (2003) Chem. Res. Toxicol., 16(2), 123-128.
56. Haasio, K.; Lounatmaa, K. and Sukura, A. (2002) Exp. Toxicol. Pathol., 54(1), 9-14.
57. Korlipara, L.V.P.; Cooper, J.M. and Schapira, A.H.V. (2004) Neuropharmacology, 46(4), 562-569.
58. Nissinen, E.; Kaheinen P.; Penttilä, K.E.; Kaivola, J. and Linden, I.B. (1997) Eur. J. Pharmacol., 340(2-3), 287-294.
59. Forsberg, M.; Lehtonen, M.; Heikkinen, M.; Savolainen, J.; Jarvinen, T. and Mannisto, P.T. (2003) J. Pharmacol. Exp. Ther., 304(2), 498-506.
60. Lautala, P.; Ethell, B.T.; Taskinen, J. and Burchell, B. (2000) Drug Metab. Dispos., 28(11), 1385-1389.
61. Haasio, K.; Koponen, A.; Penttilä, K.E. and Nissinen, E. (2002) Eur. J. Pharmacol., 453(1), 21-26.
62. Fosslien, E. (2001) Ann. Clin. Lab. Sci., 31(1), 25-67.
63. DiMauro, S. and Schon, E.A. (2003) N. Engl. J. Med., 348(26), 2656-2668.
64. Van Steenbergen, W.; Peeters, P.; De Bondt, J.; Staessen, D.; Büscher, H.; Laporta, T.; Roskams, T. and Desmet, V. (1998) J. Hepatol., 29(1), 135-141.
65. Andrade, R.J.; Lucena, M.I.; Fernandez, M.C. and Gonzales, M. (2000) J. Hepatol., 32(1), 174.
66. Schattner, A.; Sokolovskaya, N. and Cohen, J. (2000) J. Intern. Med., 247(1), 153-155.
67. Conforti, A.; Leone, R.; Moretti, U.; Mozzo, F. and Velo, G. (2001) Drug Safety, 24(14), 1081-1090.
68. Merlani, G.; Fox, M.; Oehen, H.P.; Cathomas, G.; Renner, E.L.; Fattinger, K.; Schneemann, M. and Kullak-Ublik, G.A. (2001) Eur. J. Clin. Pharmacol., 57(4), 321-326.
69. Sbeit, W.; Krivoy, N.; Shiller, M.; Farah, R.; Cohen, H.I.; Struminger, L. and Reshef, R. (2001) Ann. Pharmacother., 35(9), 1049-1052.
70. Macia, M.A.; Carvajal, A.; Del Pozo, J.G.; Vera, E. and Del Pino, A. (2002) Clin. Pharmacol. Ther., 72(5), 596-597.
71. Rodrigo, L.; De Francisco, R.; Perez-Pariente, J.M.; Cadahia, V.; Tojo, R.; Rodriguez, M.; Lucena, M.I. and Andrade, R.J. (2002) Scand. J. Gastroenterol., 37(11), 1341-1343.
72. Stadlmann, S.; Zoller, H.; Vogel, H. and Offner, F.A. (2002) Virch. Arch., 440(5), 553-555.
73. Traversa, G.; Bianchi, C.; Da Cas, R.; Abraha, I.; Menniti-Ippolito, F. and Venegoni, M. (2003) Br. J. Med., 327(7405), 18-22.
74. Gallelli, L.; Ferraro, M.; Mauro, G.F.; De Fazio, S. and De Sarro, G. (2005) Clin. Drug Invest., 25(6), 421-424
75. Boelsterli, U.A. (2002) Drug Safety, 25(9), 633-648.
76. Lewis, W.; Day, B.J. and Copeland, W.C. (2003) Nat. Rev. Drug Discov., 2(10), 812-822.
77. Davis, R. and Brogden, R.N. (1994) Drugs, 48(3), 431-454.
78. Bernareggi, A. (1998) Clin. Pharmacokinet., 35(4), 247-274.
79. Kucukguzel, S.G.; Kucukguzel, I.; Oral, B.; Sezen, S. and Rollas, S. (2005) Eur. J. Drug Metab. Pharmacokinet., 30(1-2), 127-134.
80. Caparroz-Assef, S.M.; Salgueiro-Pagadigorria, C.L.; Bersani-Amado, C.A.; Bracht, A.; Kelmer-Bracht, A.M. and Ishii-Iwamoto, E.L. (2001) Cell Biochem. Funct., 19(2), 117-124.
81. Ong, M.M.K.; Wang. A.S.; Leow, K.Y.; Khoo, Y.M. and Boelsterli, U.A. (2006) Free Radic. Biol. Med., 40(3), 420-429.
82. Boelsterli, U.A. (2003) Toxicol. Mech. Methods, 13(1), 3-20.
83. Black, M.; Rabin, L. and Schatz, N. (1980) Ann. Intern. Med., 92(1), 62-64.
84. Sharp, J.R.; Ishak, K.G. and Zimmerman, H.J. (1980) Ann. Intern. Med., 92(1), 14-19.
85. Youngman, R.J.; Osswald, W.F. and Elstner, E.F. (1982) Biochem. Pharmacol., 31(23), 3723-3729.
86. Hoener, B.; Noach, A.; Andrup, M. and Yen, T.S. (1989) Pharmacology, 38(6), 363-373.
87. Mollison, L.C.; Angus, P.; Richards, M.; Jones, R.M. and Ireton, J. (1992) Med. J. Aust., 156(5), 347-349.
88. Silva, J.M.; Khan, S. and Obrien, P.J. (1993) Arch. Biochem. Biophys., 305(2), 362-369.
89. Klee, S.; Nurnberger, M.C. and Ungemach, F.R. (1994) Chem. Biol. Interact., 93(2), 91-102.
90. Kelly, B.D.; Heneghan, M.A.; Bennani, F.; Connolly, C.E. and O'Gorman, T.A. (1998) Am. J. Gastroenterol., 93(5), 819-821.
91. Utili, R.; Boitnott, J.K. and Zimmerman, H.J. (1977) Gastroenterology, 72(4 Pt 1), 610-616.
92. Rossi, L.; Silva, J.M.; McGirr, L.G. and O'Brien, P.J. (1988) Biochem. Pharmacol., 37(16), 3109-3117.
93. Moreno, S.N.J.; Mason, R.P. and Docampo, R. (1984) J. Biol. Chem., 259(10), 6298-6305.
94. Armstrong, J.S. and Jones, D.P. (2002) FASEB J., 16(10), 1263-1265.
95. Stäubli, A. and Boelsterli, U.A. (1998) Am. J. Physiol. (Gastrointest. Liver Physiol.), 274(6 Pt 1), G1031-G1037.
96. Streeter, A.J. and Hoener, B.A. (1988) Pharm. Res., 5(7), 434-436.
97. Gomez, J.L.; Dupont, A.; Cusan, L.; Tremblay, M.; Suburu, R.; Lemay, M. and Labrie, F. (1992) Am. J. Med., 92(5), 465-470.
98. Wysowski, D.K.; Freiman, J.P.; Tourtelot, J.B. and Horton, M.L. 3rd. (1993) Ann. Int. Med., 118(11), 860-864.
99. Pontiroli, L.; Sartori, M.; Pittau, S.; Morelli, S.; Boldorini, R. and Albano, E. (1998) Ital. J. Gastroenterol. Hepatol., 30(3), 310-314.
100. Thole, Z.; Manso, G.; Salgueiro, E.; Revuelta, P. and Hidalgo, A. (2004) Urol. Int., 73(4), 289-295.
101. Dawson, L.A.; Chow, E. and Morton, G. (1997) Urology, 49(2), 283-284.
102. Cockshott, I.D. (2004) Clin. Pharmacokinet., 43(13), 855-878.
103. Wang, H.X.; Ma, X.C.; Deng, Q.L. and Li, D. (2002) Acta Pharmacol. Sin., 23(6), 562-566.
104. Wang, H.X.; Liu, X.; Xu, C.J.; Ma, X.C.; Long, J.E. and Li, D. (2005) Acta Pharmacol. Sin., 26(11), 1382-1386.
105. Coe, K.J.; Nelson, S.D.; Ulrich, R.G.; He, Y.; Dai, X.; Cheng, O.; Caguyong, M.; Roberts, C.J. and Slatter, J.G. (2006) Drug Metab. Dispos., (in press).
106. Nunez-Vergara, L.J.; Ortiz, M.E.; Bollo, S. and Squella, J.A. (1997) Chem.- Biol. Interact, 106(1), 1-14.
107. Pietta, P.; Rava, A. and Biondi, P. (1981) J. Chromatogr., 210(3), 516-521.
108. Mason, R.P. and Trumbore, M.W. (1996) Biochem. Pharmacol., 51(5), 653-660.
109. Mason, R.P.; Mak, I.T.; Trumbore, M.W. and Mason, P.E. (1999) Am. J. Cardiol., 84(4A), 16L-22L.
110. Buss, W.C.; Savage, D.D.; Stepanek, J.; Little, S.A. and McGuffee, L.J. (1988) Eur. J. Pharmacol., 152(3), 247-253.
111. Acuna, G.; Foernzler, D.; Leong, D.; Rabbia, M.; Smit, R.; Dorflinger, E.; Gasser, R.; Hoh, J.; Ott, J.; Borroni, E.; To, Z.; Thompson, A.; Li, J.; Hashimoto, L. and Lindpaintner, K. (2002) Pharmacogenomics J., 2(5), 327-334.
112. Roth, R.A.; Luyendyk, J.P.; Maddox, J.F. and Ganey, P.A. (2003) J. Pharmacol. Exp. Ther, 307(1), 1-8.
113. Tatsumi, K.; Kitamura, S. and Narai, N. (1986) Cancer Res., 46(3), 1089-1093.