Cytochrome P450-dependent toxicity of dapsone in human erythrocytes

Journal of Applied Toxicology

Volumn 30, Issue 3, 2010, Pages 271-275

  Ganesan, Shobana ^a,b   Sahu, Rajnish ^a   Walkera, Larry A ^a,b   Tekwani, Babu L ^a,b  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

4 ; 4 diaminodiphenylsulfone; CYP2C19; Cytochrome P450; Dapsone; Hemotoxicity; Methemoglobin

Indexed keywords

CHLORAMPHENICOL; CIMETIDINE; CYTOCHROME P450 2B6; CYTOCHROME P450 2C19; CYTOCHROME P450 2D6; CYTOCHROME P450 3A4; DAPSONE; GLUCOSE 6 PHOSPHATE DEHYDROGENASE; METHEMOGLOBIN; ANTIINFECTIVE AGENT; ANTIPROTOZOAL AGENT; CYP2C19 PROTEIN, HUMAN; CYP3A4 PROTEIN, HUMAN; CYTOCHROME P450; CYTOCHROME P450 3A; HEMOLYTIC AGENT; ISOENZYME; N DEMETHYLASE; RECOMBINANT PROTEIN; S MEPHENYTOIN N DEMETHYLASE; S-MEPHENYTOIN N-DEMETHYLASE; UNSPECIFIC MONOOXYGENASE;

ANIMAL TISSUE; ARTICLE; BLOOD TOXICITY; CONTROLLED STUDY; ERYTHROCYTE; FEMALE; HUMAN; HUMAN CELL; HUMAN TISSUE; LIVER MICROSOME; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; ANIMAL; BIOTRANSFORMATION; DRUG ANTAGONISM; DRUG EFFECT; METABOLISM; OSMOLARITY;

ANIMALS; ANTI-BACTERIAL AGENTS; ANTIPROTOZOAL AGENTS; ARYL HYDROCARBON HYDROXYLASES; BIOTRANSFORMATION; CYTOCHROME P-450 CYP2D6; CYTOCHROME P-450 CYP3A; CYTOCHROME P-450 ENZYME SYSTEM; DAPSONE; ERYTHROCYTES; HEMOLYTIC AGENTS; HUMANS; ISOENZYMES; MALE; METHEMOGLOBIN; MICE; MICROSOMES, LIVER; OSMOLAR CONCENTRATION; OXIDOREDUCTASES, N-DEMETHYLATING; RECOMBINANT PROTEINS;

EID: 77951574997     PISSN: 0260437X     EISSN: 10991263     Source Type: Journal    
DOI: 10.1002/jat.1493     Document Type: Article

References (27)

1. Bloom KE, Brewer GJ, Magon AM, Wetterstroem N.1983. Microsomal incubation test of potentially hemolytic drugs for glucose-6-phosphate dehydrogenase deficiency. Clin. Pharmacol. Ther. 33: 403-409. (Pubitemid 13093757)
2. Coleman MD.1995. Dapsone toxicity: some current perspectives. Gen. Pharmacol. 26: 1461-1467.
3. Coleman MD, Jacobus DP.1993. Reduction of dapsone hydroxylamine to dapsone during methaemoglobin formation in human erythrocytes in vitro - II. Movement of dapsone across a semipermeable membrane into erythrocytes and plasma. Biochem. Pharmacol. 46: 1363-1368.
4. Cucinell SA, Israili ZH, Dayton PG. 1972. Microsomal N-oxidation of dapson as a cause of methemoglobin formation in human red cells. Am. J. Trop. Med. Hyg. 21: 322-331.
5. Desta Z, Zhao X, Shin JG, Flockhart DA. 2002. Clinical significance of the cytochrome CYP2C19 genetic polymorphism. Clin. Pharmacokinet. 41: 913-958 (Pubitemid 35168437)
6. Evelyn KA, Malloy HT.1938. Microdetermination of oxyhemoglobin, methemoglobin, and sulfhemoglobin in a single sample of blood. J. Biol. Chem. 126: 655-662.
7. Ganesan S, Tekwani BL, Sahu R, Tripathi LM, Walker LA. 2009. Cytochrome P(450)-dependent toxic effects of primaquine on human erythrocytes. Toxicol. Appl. Pharmacol.; doi: 10.1016/j.taap.2009.07.012.
8. Grossman S., Budinsky R., Jollow, D.1995. Dapsone-induced hemolytic anemia: role of glucose-6-phosphate dehydrogenase in the hemolytic response of rat erythrocytes to N-hydroxydapsone. J. Pharmacol. Exp. Ther. 273: 870-877
9. Halmekoski J., Mattila MJ, Mustakallio KK. 1978. Metabolism and haemolytic effect of dapsone and its metabolites in man. Med. Biol. 56: 216-221. (Pubitemid 9040002)
10. Harley JD, Mauer AM.1960. Studies on the formation of Heinz bodies. I. Methemoglobin production and oxyhemoglobin destruction. Blood. 16: 1722-1735.
11. Hjelm M., de Verdier CH.1965. Biochemical effects of aromatic amines - I. Methemoglobinemia, Haemolysis and Heinz-body formation induced by 4,4′-diaminodiphenylsulphone. Biochem. Pharmacol. 14: 1119-1128
12. Hutzler JM, Hauer MJ, Tracy TS. 2001. Dapsone activation of CYP2C9-mediated metabolism: evidence for activation of multiple substrates and a two-site model. Drug. Metab. Dispos. 29: 1029-1034.
13. Irshaid Y, Branch RA, Adedoyin A. 1996. Metabolic interactions of putative cytochrome P4503A substrates with alternative pathways of dapsone metabolism in human liver microsomes. Drug. Metab. Dispos. 24: 164-171. (Pubitemid 26063905)
14. Li XQ, Björkman A, Andersson TB, Gustafsson LL, Masimirembwa CM. 2003. Identification of human cytochrome P(450)s that metabolize anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur. J. Clin. Pharmacol. 59: 429-442. (Pubitemid 37214951)
15. McMillan DC, Jensen CB, Jollow DJ. 1998. Role of lipid peroxidation in dapsone-induced hemolytic anemia. J. Pharmacol. Exp. Ther. 287: 868-876. (Pubitemid 29131594)
16. McMillan DC, Powell CL, Bowman ZS, Morrow JD, Jollow DJ. 2005. Lipids versus proteins as major targets of pro-oxidant, direct-acting hemolytic agents. Toxicol. Sci. 88: 274-283
17. Mitra AK, Thummel KE, Kalhorn TF, Kharasch ED, Unadkat JD, Slattery JT.1995. Metabolism of dapsone to its hydroxylamine by CYP2E1 in vitro and in vivo. Clin. Pharmacol. Ther. 58: 556-566.
18. Persson I, Aklillu E, Rodrigues F, Bertilsson L, Ingelman-Sundberg M. 1996. S-Mephenytoin hydroxylation phenotype and CYP2C19 genotype among Ethiopians. Pharmacogenetics 6: 521-526. (Pubitemid 27032304)
19. Reilly TP, Woster PM, Svensson CK. 1999. Methemoglobin formation by hydroxylamine metabolites of sulfamethoxazole and dapsone: implications for differences in adverse drug reactions. J. Pharmacol. Exp. Ther. 288: 951-959.
20. Rhodes LE, Tingle MD, Park BK, Chu P, Verbov JL, Friedmann PS. 1995. Cimetidine improves the therapeutic/toxic ratio of dapsone in patients on chronic dapsone therapy. Br. J. Dermatol. 132: 257-262.
21. Scott GL, Rasbridge MR. 1973. The in vitro action of dapsone and its derivatives on normal and G6PD-deficient red cells. Br. J. Haematol. 24: 307-317.
22. Tingle MD, Mahmud R, Maggs JL, Pirmohamed M, Park BK.1997. Comparison of the metabolism and toxicity of dapsone in rat, mouse and man. J. Pharmacol. Exp. Ther. 283: 817-823. (Pubitemid 27514644)
23. Vage C, Svensson CK. 1994. Evidence that the biotransformation of dapsone and monoacetyl dapsone to their respective hydroxylamine metabolites in rat liver microsomes is mediated by cytochrome P450 2C6/2C11 and 3A1. Drug. Metab. Dispos. 22: 572-1527 (Pubitemid 24244867)
24. Vage C, Saab N, Woster PM, Svensson CK. 1994. Dapsone-induced hematologic toxicity: comparison of the methemoglobin-forming ability of hydroxylamine metabolites of dapsone in rat and human blood. Toxicol. Appl. Pharmacol. 129: 309-316. (Pubitemid 24380801)
25. Wilson JR, Harris JW. 1977. Hematologic side-effects of dapsone. Ohio State Med. J. 73: 557-560
26. Winter HR, Wang Y, Unadkat JD, 2000. CYP2C8/9 mediates dapsone N-hydroxylation at clinical concentrations of dapsone. Drug. Metab. Dispos. 28: 865-868.
27. Zhang Y, Si D, Chen X, Lin N, Guo Y, Zhou H, Zong D. 2007. Influence of CYP2C9 and CYP2C19 genetic polymorphism on pharmacokinetics of glizazide MR in Chinese subjects, Br. J. Clin. Pharmacol. 64: 67-74 (Pubitemid 46934414)