Comparison of the metabolism and toxicity of dapsone in rat, mouse and man

Journal of Pharmacology and Experimental Therapeutics

Volumn 283, Issue 2, 1997, Pages 817-823

  Tingle, M D ^a,c   Mahmud, R ^b,c   Maggs, J L ^c   Pirmohamed, M ^c   Park, B K ^c  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b SCHOOL OF PHYSICS   (Malaysia)

^c UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DAPSONE; DRUG METABOLITE; GLUCURONIDE; HYDROXYLAMINE; METHEMOGLOBIN;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BILE; DRUG METABOLISM; DRUG TOXICITY; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HUMAN TISSUE; INTRAARTERIAL DRUG ADMINISTRATION; INTRAPERITONEAL DRUG ADMINISTRATION; MALE; MASS SPECTROMETRY; METHEMOGLOBINEMIA; MICROSOME; MOUSE; NONHUMAN; NORMAL HUMAN; PRIORITY JOURNAL; RAT; SPECIES DIFFERENTIATION; URINALYSIS;

ACETYLATION; ANIMALS; ANTI-INFECTIVE AGENTS; CARBON RADIOISOTOPES; DAPSONE; ERYTHROCYTES; FEMALE; HUMANS; MALE; METHEMOGLOBIN; MICE; RATS; RATS, WISTAR; SPECIES SPECIFICITY;

EID: 0030815886     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (45)

1. AGAR, N. S. AND HARLEY, J. D.: Erythrocytic methaemoglobin reductases of various mammalian species. Experimentia. 28: 1248-1249, 1972.
2. BODANSKY, O.: Methaemoglobinaemia and methaemoglobin-producing compounds. Pharmacol. Rev. 3: 144-196, 1951.
3. BOOTH, S. A., MOODY, C. E., DAHL, M. V., HERRON, M. J. AND NELSON, R. D.: Dapsone suppresses integrin-mediated neutrophil adherence function. J. Invest. Dermatol. 98: 135-140, 1992.
4. BOZEMAN, P. M., LEARN, D. B. AND THOMAS, E. L.: Inhibition of the human leukocyte enzymes myeloperoxidase and eosinophil peroxidase by dapsone. Biochem. Pharmacol. 44: 553-563, 1992.
5. CHATTERJEE, K. R. AND PODDAR, R. K.: Radioactive tracer studies on the uptake of diaminodiphenylsulphone by leprosy patients. Proc. Soc. Exp. Biol. 94: 122-125, 1957.
6. COLEMAN, M. D. AND TINGLE, M. D.: Use of a metabolic inhibitor to reduce dapsone-dependent haematological toxicity. Drug Dev. Res. 25: 1-16, 1992.
7. COLEMAN, M. D., HOAKSEY, P. E., BRECKENRIDGE, A. M. AND PARK, B. K.: Inhibition of dapsone-induced methaemoglobinaemia in the rat isolated perfused liver. J. Pharm. Pharmacol. 42: 302-307, 1990a.
8. COLEMAN, M. D., SCOTT, A. K., BRECKENRIDGE, A. M. AND PARK, B. K.: The use of cimetidine as a selective inhibitor of dapsone N-hydroxylation in man. Br. J. Clin. Pharmacol. 30: 761-769, 1990b.
9. COLEMAN, M. D., TINGLE, M. D., WINN, M. J. AND PARK, B. K.: Gonadal influence on the metabolism and haematological toxicity of dapsone in the rat. J. Pharm. Pharmacol. 42: 698-703, 1990c.
10. COLEMAN, M. D., TINGLE, M. D., HUSSAIN, F., STORR, R. C. AND PARK, B. K.: An investigation into the haematological toxicity of structural analogues of dapsone in vivo and in vitro. J. Pharm. Pharmacol. 43: 779-784, 1991.
11. COLEMAN, M. D., SMITH, S. N., KELLY, D. E., KELLY, S. L. AND SEYDEL, J. K.: Studies on the toxicity of novel analogues of dapsone in vitro using rat, human and heterologously expressed metabolising systems. J. Pharm. Pharmacol. 48: 945-950, 1996.
12. COLWELL, W. T., CHAN, G., BROWN, V. H., DEGRAW, J. I. AND PETERS, J. H.: Potential antileprotic agents. 1. Inhibition of a model mycobacterial system by diaryl sulfones. J. Med. Chem. 17: 142-144, 1974.
13. CRIBB, A. E., SPIELBERG, S. P. AND GRIFFIN, G. P.: N4-Hydroxylation of sulphamethoxazole by cytochrome P450 of the cytochrome P4502C subfamily and reduction of sulphamethoxazole hydroxylamine in human and rat hepatic microsomes. Drug Metab. Dispos. 23: 406-414, 1995.
14. DE BENEDETTI, P. G., IAROSSI, D., MENZIANI, C. AND FRASSINETI, T.: Quantitative structure-activity activity analysis in dihydropteroate synthase inhibition studies. Comparison with sulphonamides. J. Med. Chem. 30: 459-464, 1987.
15. DE GOWIN, R. L., EPPES, R. B., POWELL, R. D. AND CARSON, P. E.: The haemolytic effects of diaphenylsulphone (DDS) in normal subjects and in those with glucose 6-phosphate dehydrogenase deficiency. Bull. W.H.O. 35: 165-179, 1966.
16. ENTWISTLE, I. D., GILKERSON, T., JOHNSTONE, R. A. W. AND TELFORD, R. P.: Rapid catalytic transfer reduction of aromatic nitro compounds to hydroxylamines. Tetrahedron 34: 213-215, 1978.
17. GANER, A., KNOBEL, B., FRYD, C. H. AND RACHMILEWITZ, E. A.: Dapsone-induced methaemoglobinaemia and hemolysis in the presence of familial hemoglobinopathy hasharon and familial methaemoglobin reductase deficiency. Isr. J. Med. Sci. 17: 703-704, 1981.
18. GELBER, R., PETERS, J. H., GORDON, G. S., GLAZKO, A. J. AND LEVY, L.: The polymorphic acetylation of dapsone in man. Clin. Pharmacol. Ther. 12: 235-238, 1971.
19. GILL, H. J., TINGLE, M. D. AND PARK, B. K.: N-hydroxylation of dapsone by multiple enzymes of cytochrome P450: implications for inhibition of haemotoxicity. Br. J. Clin. Pharmacol. 40: 531-539, 1995.
20. GIRARD, P.-M., LANDMAN, R., GAUDEBOUT, C., OLIVARES, R., SAIMOT, A. G., JELAZKO, P., GAUDEBOUT, C., CERTAIN, A., Bouõ, F., BOUVET, E., LECOMPTE, T., COULAUD, J.-P. AND THE PRIO STUDY GROUP.: Dapsone-pyrimethamine compared with aerosolized pentamidine as primary prophylaxis against Pneumocystis carinii and toxoplasmosis in HIV infection. N. Engl. J. Med. 328: 1514-1520, 1993.
21. GLADER, B. F. AND CONRAD, M. E.: Haemolysis by diphenylsulfones: Comparative effects of DDS and hydroxylamine-DDS. J. Lab. Clin. Med. 81: 267-272, 1973.
22. GROSSMAN, S. J. AND JOLLOW, D. J.: Role of dapsone hydroxylamine in dapsoneinduced hemolytic anemia. J. Pharmacol. Exp. Ther. 244: 118-125, 1988.
23. GUENGERICH, F. P., MARTIN, M. V., BEAUNE, P. H., KREMERS, P., WOLFF, T. AND WAXMAN, D. J.: Characterization of rat and human liver cytochrome P450 forms involved in nifedipine oxidation. A prototype for genetic polymorphism in oxidative drug metabolism. J. Biol. Chem. 261: 5051-5060, 1986.
24. HARRISON, J. H. AND JOLLOW, D. J.: Role of aniline metabolites in anilineinduced haemolytic anaemia. J. Pharmacol. Exp. Ther. 238: 1045-1054, 1986.
25. HJELM, M. AND DEVERDIER, C. H.: Biochemical effects of aromatic amines. I. Methaemoglobinaemia, haemolysis and Heinz-body formation induced by 4,4′-diaminodiphenylsulphone. Biochem. Pharmacol. 14: 1119-1128, 1965.
26. ISRAILI, Z. H., CUCINELL, S. A., VAUGHT, J., DAVIS, E., LESSER, J. M. AND DAYTON, P. G.: Studies of the metabolism of dapsone in man and experimental animals: Formulation of N-hydroxy metabolites. J. Pharmacol. Exp. Ther. 187: 138-151, 1973.
27. JORDE, U. P., HOROWITZ, H. W. AND WORMSER, G. P.: Utility of dapsone for prophylaxis of Pneumocystis carinii pneumonia in trimethoprim-sulphamethoxazole-intolerant, HIV-infected individuals. AIDS 7: 354-359, 1993.
28. KRAMER, P. A., GLADER, B. E. AND LI, T.-K.: Mechanism of methaemoglobin formation by diphenylsulfones. Effect of 4-amino-4′hydroxyaminodiphenylsulfone and other p-substituted derivatives. Biochem. Pharmacol. 21: 1265-1274, 1972.
29. MAY, D. G., PORTER, J. A., UETRECHT, J. P., WILKINSON, G. R. AND BRANCH, R. A.: The contribution of N-hydroxylation and acetylation to dapsone pharmacokinetics in normal subjects. Clin. Pharmacol. Ther. 48: 619-627, 1990.
30. MITRA, A. K., THUMMEL, K. E., KALHORN, T. F., KHARASH, E. D., UNADKAT, J. D. AND SLATTERY, J. T.: Metabolism of dapsone to its hydroxylamine by CYP2E1 in vitro and in vivo. Clin. Pharmacol. Ther. 58: 556-566, 1995.
31. POPOFF, I. C., SINGHAL, G. H. AND ENGLE, A. R.: Antimalarial agents. 7. Compounds related to 4,4′-Bis(aminophenyl)sulphone. J. Med. Chem. 14: 550-551, 1971a.
32. POPOFF, I. C., SINGHAL, G. H. AND ENGLE, A. R.: Antimalarial agents. 8. Ringsubstituted bis(4-aminophenyl) sulfones and their precursors. J. Med. Chem. 14: 1166-1169, 1971b.
33. PRUSSICK, R., MAHMOUD, A. M. A., ROSENTHAL, D. AND GUYATT, G.: The protective effect Of vitamin E on the haemolysis associated with dapsone treatment in patients with dermatitis herpetiformis. Arch. Dermatol. 128: 210-213,1992.
34. RAIZISS, G. W., CLEMENCE, L. W., SEVERAC, M. AND MOETSCH, J. C.: Chemistry and Chemotherapy of 4,4′-diaminodiphenylsulfone, 4-amino-4′-hydroxydiphenylsulfone and related compounds. J. Am. Chem. Soc. 61: 2763-2765, 1939.
35. SCOTT, G. L, AND RASBRIDGE, M. R.: The in vitro action of dapsone and its derivatives on normal and G6PD-deficient red cells. Br. J. Haematol. 24: 307-317, 1973.
36. SHANK, G. D., EDSTEIN, M. D., SURIYAMONGKOL, V., TIMSAAD, S. AND WEBSTER, H. K.: Malaria chemoprophylaxis using proguanil/dapsone combinations on the Thai-Cambodian border. Am. J. Trop. Med. Hyg. 46: 643-648, 1992.
37. THUONG-NGUYEN, V., KADUNCE, D. P., HENDRIX, J. D., GAMMON, W. R. AND ZONE, J. J.: Inhibition of neutrophil adherence to antibody by dapsone: A possible therapeutic mechanism in the treatment of IgA dermatoses. J. Invest. Dermatol. 100: 349-355, 1993.
38. TINGLE, M. D. AND PARK, B. K.: The use of a three compartment in vitro model to investigate the role of hepatic drug metabolism in drug-induced blood dyscrasias. Br. J. Clin. Pharmacol. 36: 31-39, 1993.
39. UEHLEKE, H. AND TABARELLI, S.: N-Hydroxylation of 4,4′-diaminodiphenylsulfone (dapsone) by liver microsomes and in dogs and humans. Naunyn-Schmeideberg's Arch. Pharmacol. 278: 55-68, 1973.
40. UETRECHT, J., ZAHID, N., SHEAR, N. H. AND BIGGAR, W. D.: Metabolism of dapsone to a hydroxylamine by human neutrophils and mononuclear cells. J. Pharmacol. Exp. Ther. 245: 274-279, 1988.
41. VADHER, A. AND LALLJEE, M.: Patient treatment compliance in leprosy. A critical review. Int. J. Lepr. 60: 587-607, 1992.
42. VAGE, C. AND SVENSSON, C. K.: Evidence that the biotransformation of dapsone and monoacetyldapsone to their respective hydroxylamine metabolites in rat liver microsomes is mediated by cytochrome P450 2C6/2C11 and 3A1. Drug Metab. Disp. 22: 572-577, 1994.
43. VAGE, C., SAAB, N., WOSTER, P. M. AND SVENSSON, C. K.: Dapsone-induced hematologie toxicity: Comparison of the methaemoglobin-forming ability of hydroxylamine metabolites of dapsone in rat and human blood. Toxicol. Appl. Pharmacol. 129: 309-316, 1994.
44. WIESE, M., SEYDEL, J. K., PIEPER, H., KRUGER, G., NOLL, K. R. AND KECK, J.: Multiple regression analysis of antimalarial activities of sulphones in cell-free systems and principal component analysis to compare with antibacterial activities. Quant. Struct.-Act. Relat. 6: 164-172, 1987.
45. ZUIDEMA, J., HILBERS-MODDERMAN, E. S. M. AND MERKUS, F. W. H. M.: Clinical pharmacokinetics of dapsone. Chin. Pharmacokinet. 11: 299-315, 1986.