Activation of CGS 12094 (prinomide metabolite) to 1,4-benzoquinone by myeloperoxidase: Implications for human idiosyncratic agranulocytosis

Fundamental and Applied Toxicology

Volumn 35, Issue 2, 1997, Pages 197-204

  Parrish, D D ^a   Schlosser, M J ^a,b   Kapeghian, J C ^a   Traina, V M ^a  

^a US Research Department   (United States)

^b Astra Arcus USA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE; ANTIINFLAMMATORY AGENT; CGS 12094; DRUG METABOLITE; MYELOPEROXIDASE; PRINOMIDE; UNCLASSIFIED DRUG;

AGRANULOCYTOSIS; ARTICLE; DRUG METABOLISM; HUMAN; METABOLIC ACTIVATION;

PRIMATES; RODENTIA;

EID: 85033533360     PISSN: 02720590     EISSN: None     Source Type: Journal    
DOI: 10.1006/faat.1996.2270     Document Type: Article

References (31)

1. Bird, H. A., Hill, J., Dixon, J. S., Bojar, R., Traficante, A., Catalano, M. A., Adair, S. F., Liauw, L., Sussman, H., Rotman, H., and Wright, V. (1989). A clinical and biochemical assessment of prinomide in patients with rheumatoid arthritis. J. Rheumatol 16, 448-454.
2. Bolscher, B. G. J. M., Zoutberg, G. R., Cuperus, R. A., and Weaver, R. (1984). Vitamin C stimulates the chlorinating activity of human myeloperoxidase. Biochim. Biophys. Acta 784, 189-191.
3. Davis, P., and Johnston, C. (1990). Prinomide-Immunopharmacological profile of a new antirheumatic drug. Int. J. Imm. T. 6, 61-70.
4. Eastmond, D. A., and Smith, M. T. (1990). Xenobiotic activation by stimulated human polymorphonuclear leukocytes and myeloperoxidase. Methods Enzymol. 186, 579-585.
5. Eastmond, D. A., Smith, M. T., and Irons, R. D. (1987). An interaction of benzene metabolites reproduces the myelotoxicity observed with benzene exposure. Toxicol. Appl. Pharmacol. 91, 85-95.
6. Egger, H., Itterly, W., John, V., Rodebaugh, R., Shimanskas, C., Stancato, F., and Kapoor, A. (1988). Disposition and metabolism of prinomide in laboratory animals. Drug Metab. Dispos. 16, 568-575.
7. Fischer, V., Haar, J. A., Greiner, L., Lloyd, R. V., and Mason, R. P. (1992). Clozapine - Possible role of free radical formation in clozapine (Clozaril)-induced agranulocytosis. Mol. Pharmacol. 40, 846-853.
8. Green, J. D., Yau, E. T., Traina, V. M., Katz, R., Arthur, A. T., and Diener, R. M. (1983). Preclinical safety evaluation of CGS 10787B - A new anti-inflammatory compound. J. Am. Coll. Toxicol. 2, 249-254.
9. Heimpel, H. (1988). Drug-induced agranulocytosis. Med. Toxicol. 3, 449-462.
10. Hofstra, A. H., Li-Muller, S. M. A., and Uetrecht, J. P. (1992). Metabolism of isoniazid by activated leukocytes: Possible role in drug-induced lupus. Drug Metab. Dispos. 20, 205-210.
11. Kochak, G. M., Pai, S., Iannucci, R., Hone, F., Kachmar, D., Perrino, P., and Egger, H. (1993). Prinomide tromethamine pharmacokinetics: Mutually dependent saturable and competitive protein binding between prinomide and its own metabolite. Pharm. Res. 10, 49-55.
12. Lunte, S. M., and Kissinger, P. T. (1984). The use of liquid chromatography with dual-electrode electrochemical detection in the investigation of glutathione oxidation during benzene metabolism. J. Chromatogr. 317, 579-588.
13. Marquez, L. A., Dunford, H. B., and Van Wart, H. (1990). Kinetic studies on the reaction of compound II of myeloperoxidase with ascorbic acid. J. Biol. Chem. 265, 5666-5670.
14. O'Brien, P. J. (1988a). Oxidants formed by the respiratory burst: Their physiological role and their involvement in the oxidative metabolism and activation of drugs, carcinogens, and xenobiotics. In The Respiratory Burst and Its Physiological Significance (A. J. Sbarra and R. R. Strauss, Eds.), pp. 203-232. Plenum, New York.
15. O'Brien, P. J. (1988b). Radical formation during the peroxidase catalyzed metabolism of carcinogens and xenobiotics: The reactivity of these radicals with GSH, DNA, and unsaturated lipid. Free Radical Biol. Med. 4, 169-183.
16. O'Brien, P. J., Khan, S., and Jatoe, S. D. (1991). Formation of biological reactive intermediates by peroxidases: Halide mediated acetaminophen oxidation and cytotoxicity. In Advances in Experimental Medicine and Biology, Biological Reactive Intermediates IV, Molecular and Cellular Effects and Their Impact on Human Health (C. C. Winter, R. R. Snyder, D. J. Jollow, G. F. Kalf, J. J. Kocsis, and I. G. Sipes, Eds.), pp. 121-132. Plenum, New York.
17. Pirozzi, S. J., Schlosser, M. J., and Kalf, G. F. (1989). Prevention of benzene-induced myelotoxicity and prostaglandin synthesis in bone marrow of mice by inhibitors of prostaglandin H synthase. Immunopharmacology 18, 39-55.
18. Schlosser, M. J., and Kalf, G. F. (1989). Metabolic activation of hydroquinone by macrophage peroxidases. Chem.-Biol. Interact. 72, 191-207.
19. Schlosser, M. J., Shurina, R. D., and Kalf, G. F. (1989). Metabolism of phenol and hydroquinone to reactive products by macrophage peroxidase or purified prostaglandin H synthase. Environ. Health Perspect. 82, 229-237.
20. Schlosser, M. J., Shurina, R. D., and Kalf, G. F. (1990). Prostaglandin H synthase catalyzed oxidation of hydroquinone to a sulfhydryl binding and DNA damaging metabolite. Chem. Res. Toxicol. 3, 333-339.
21. Smith, M. T., Yager, J. W., Steinmetz, K. L., and Eastmond, D. A. (1989). Peroxidase-dependent metabolism of benzene's phenolic metabolites and its potential role in benzene toxicity and carcinogenicity. Environ. Health Perspect. 82, 23-29.
22. Thomas, D. J., Reasor, M. J., and Wierda, D. (1989). Macrophage regulation of myelopoiesis is altered by exposure to the benzene metabolite hydroquinone. Toxicol. Appl. Pharmacol. 79, 440-453.
23. Thomas, D. J., Sadler, A., Subrahmanyam, V. V., Siegal, D., Reasor, M. J., Wierda, D., and Ross, D. (1990). Bone marrow stromal cell bioactivation and detoxification of the benzene metabolite hydroquinone: Comparison of macrophages and fibroblastoid cells. Mol. Pharmacol. 37, 255-262.
24. Uetrecht, J. P. (1988). Drug-induced agranulocytosis and other effects mediated by peroxidases during the respiratory burst. In The Respiratory Burst and Its Physiological Significance (A. J. Sbarra and R. R. Strauss, Eds.), pp. 233-243. Plenum, New York.
25. Uetrecht, J. P. (1989a). Idiosyncratic drug reactions: Possible role of reactive metabolites generated by leukocytes. Pharm. Res. 6, 265-273.
26. Uetrecht, J. (1989b). Mechanisms of hypersensitivity reactions: Proposed involvement of reactive metabolites generated by activated leukocytes. Trends Pharmacol. Sci. 10, 463-467.
27. Uetrecht, J. (1990). Drug metabolism by leukocytes and its role in drug induced lupus and other idiosyncratic drug reactions. CRC Crit. Rev. Toxicol. 20, 213-235.
28. Uetrecht, J., and Zahid, N. (1988). N-Chlorination of phenytoin by myeloperoxidase to a reactive metabolite. Chem-Res. Toxicol. 1, 148-151.
29. Van Zyl, J. M., Basson, K., Kriegler, A., and Van De Walt, B. J. (1990). Activation of chlorpromazine by the myeloperoxidase system of the human neutrophil. Biochem. Pharmacol. 40, 947-954.
30. Wasil, M., Halliwell, B., Moorhouse, C. P., Duncan, C., Hutchison, S., and Baim, H. (1987). Biologically significant scavenging of the myeloperoxidase-derived oxidant hypochlorous acid by some anti-inflammatory drugs. Biochem. Pharm. 36, 3847-3850.
31. Zuurbier, K. W. M., Bakkenist, A. R. J., Wever, R., and Muijser, A. O. (1990). The chlorinating activity of human myeloperoxidase: High initial activity at neutral pH value and activation by electron donors. Biochim. Biophys. Acta 1037, 140-146.