Inhibition of sulfamethoxazole hydroxylamine formation by fluconazole in human liver microsomes and healthy volunteers

Clinical Pharmacology and Therapeutics

Volumn 59, Issue 3, 1996, Pages 332-340

  Mitra, Ashoke K ^a,b   Thummel, Kenneth E ^a   Kalhorn, Thomas F ^a   Kharasch, Evan D ^a   Unadkat, Jashvant D ^a   Slattery, John T ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

^b PROCTER AND GAMBLE COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; DRUG METABOLITE; FLUCONAZOLE; HYDROXYLAMINE; KETOCONAZOLE; SULFAMETHOXAZOLE; SULFAMETHOXAZOLE HYDROXYLAMINE; UNCLASSIFIED DRUG;

ADULT; AREA UNDER THE CURVE; ARTICLE; DRUG ANTAGONISM; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG ELIMINATION; DRUG HALF LIFE; DRUG METABOLISM; ENZYME INHIBITION; HUMAN; HUMAN CELL; HUMAN EXPERIMENT; IN VITRO STUDY; IN VIVO STUDY; LIVER MICROSOME; MALE; NORMAL HUMAN; ORAL DRUG ADMINISTRATION; PRIORITY JOURNAL;

ADULT; ANTIFUNGAL AGENTS; CIMETIDINE; FLUCONAZOLE; HISTAMINE H2 ANTAGONISTS; HUMANS; KETOCONAZOLE; MALE; MICROSOMES, LIVER; REFERENCE VALUES; SULFAMETHOXAZOLE;

EID: 0029879648     PISSN: 00099236     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-9236(96)80011-7     Document Type: Article

References (34)

1. Lee BL, Medina I, Benowitz NL, Jacob P, Wofsy CB, Mills J. Dapsone, trimethoprim and sulfamethoxazole plasma levels during treatment of Pneumocystis pneumonia in patients with acquired immunodeficiency syndrome: evidence of drug interactions. Ann Intern Med 1989;110:606-11.
2. Medina I, Mills J, Leoung G, et al. Oral therapy for pneumocystis carinii pneumonia in the acquired immunodeficiency syndrome: a controlled trial of trimethoprim-sulfamethoxazole versus dapsone-trimethoprim. N Engl J Med 1990;323:776-82.
3. Kovacs JA, Hiementz JW, Macher AM, et al. Pneumocystis carinii pneumonia: a comparison between patients with the acquired immunodeficiency syndrome and patients with other immunodeficiencies. Ann Intern Med 1984;100:66-71.
4. Gordon FM, Simon GL, Wofsy CB, Mills J. Adverse reactions to trimethoprim-sulfamethoxazole in patients with the acquired immunodeficiency syndrome. Ann Intern Med 1984;100:495-9.
5. Mandell GL, Sande MA. Antimicrobial agents (cont): sulfonamides, trimethoprim-sulfamethoxazole, quinolones, and agents for urinary tract infections. In: Gilman AG, Rall TW, Nies AS, Taylor P, eds. The pharmacological basis of therapeutics. 8th ed. New York: Pergamon Press, 1990:1047-64.
6. Mandell GL, Sande MA. Antimicrobial agents (cont): drugs used in the chemotherapy of tuberculosis and leprosy. In: Gilman AG, Rall TW, Nies AS, Taylor P, eds. The pharmacological basis of therapeutics. 8th ed. New York: Pergamon Press, 1990:1146-64.
7. Hughes WT, Kennedy W, Dugdale M, et al. Prevention of pneumocystis carinii pneumonitis in AIDS patients with weekly dapsone [Letter]. Lancet 1990;336: 1066.
8. Park BK, Coleman JW, Kitteringham NR. Drug disposition and drug hypersensitivity. Biochem Pharmacol 1987;36:581-90.
9. Shear NH, Spielberg SP, Grant DM, Tang BK, Kalow W. Differences in metabolism of sulfonamides predisposing to idiosyncratic toxicity. Ann Intern Med 1986; 105:179-84.
10. Rieder MJ, Uetrecht J, Cannon M, Miller M, Spielberg SP. Diagnosis of sulfonamide hypersensitivity reactions by in vitro "rechallenge" with hydroxylamine metabolites. Ann Intern Med 1989;110:286-9.
11. Kiese M. The biochemical production of ferrihemoglobin-forming derivatives from aromatic amines and mechanisms of ferrihemoglobin formation. Pharmacol Rev 1966;18:1091-161.
12. Cribb AE, Spielberg SP. Hepatic microsomal metabolism of sulfamethoxazole to the hydroxylamine. Drug Metab Dispos 1990;18:784-7.
13. Cribb AE, Spielberg SP. An in vitro investigation of predisposition to sulfonamide idiosyncratic reactions in dogs. Vet Res Commun 1990;14:241-52.
14. Cribb AE, Spielberg SP. Sulfamethoxazole is metabolized to the hydroxylamine in humans. CLIN PHARMACOL THER 1992;51:552-6.
15. Mitra AK, Kalhorn TF, Thummel KE, Unadkat JD, Slattery JT. Metabolism of arylamines by human liver microsomal cytochrome P-450(s) [Abstract]. XSSX 1993;4:148.
16. Thummel KE, Kharasch ED, Podoll T, Kunze K. Human liver microsomal enflurane defluorination catalyzed by cytochrome P-450 2E1. Drug Metab Dispos 1993;21:350-7.
17. Thummel KE, Lee CA, Kunze KL, Nelson SD, Slattery JT. Oxidation of acetaminophen to N-acetyl-p-benzoquinone imine by human CYP3A4. Biochem Pharmacol 1993;45:1563-9.
18. Lowry OH, Rosenbrough NJ, Farr AL, Randall RJ. Protein measurement with the Folin phenol reagent. J Biol Chem 1951;193:265-75.
19. Cribb AE, Miller M, Leeder JS, Hill J, Spielberg SP. Reactions of the nitroso and hydroxylamine metabolites of sulfamethoxazole with reduced glutathione. Implications for idiosyncratic toxicity. Drug Metab Dispos 1991;19:900-6.
20. Hosotsubo KK, Hosotsubo H, Nishijima MK, Okada T, Taenaka N, Yoshiya I. Rapid determination of serum levels of a new antifungal agent, fluconazole, by high performance liquid chromatography. J Chromatogr 1990;529:223-8.
21. Shaw PN, Houston JB. Kinetics of drug metabolism inhibition: Use of metabolic concentration-time profiles. J Pharmacokinet Biopharm 1987;15:497-510.
22. Shear NH, Spielberg SP, Grant DM, Tang BK, Kalow W. Differences in metabolism of sulfonamides predisposing to idiosyncratic toxicity. Ann Intern Med 1986; 105:179-84.
23. Somogyi A, Gugler R. Drug interactions with cimetidine. Clin Pharmacokinet 1982;7:23-41.
24. Jensen JC, Gugler R. Cimetidine interaction with liver microsomes in vitro and in vivo: involvement of an activated complex with cytochrome P-450. Biochem Pharmacol 1985;34:2141-6.
25. Tingle MD, Coleman MD, Park BK. The effect of preincubation with cimetidine on the N-hydroxylation of dapsone by human liver microsomes. Br J Clin Pharmacol 1991;32:120-3.
26. Morita K, Konishi H, Shimakawa H. Fluconazole: a potent inhibitor of cytochrome P-450 dependent drug metabolism in mice and humans in vivo. Comparative study with ketoconazole. Chem Pharm Bull (Tokyo) 1992;40:1247-51.
27. Blum RA, Wilton JH, Hilligoss DM, et al. Effect of fluconazole on the disposition of phenytoin. CLIN PHARMACOL THER 1991;49:420-5.
28. Vree TB, Hekster YA, Baars AM, Damsma JE, van der Kleijn E. Pharmacokinetics of sulfamethoxazole in man. Clin Pharmacokinet 1978;3:319-29.
29. Cribb AE, Miller M, Tesoro A, Spielberg SP. Peroxidase-dependent oxidation of sulfonamides by monocytes and neutrophils from humans and dogs. Mol Pharmacol 1990;38:744-51.
30. Larsson R, Ross D, Berlin T, Olsson LI, Moldéus P. Prostaglandin synthase catalyzed metabolic activation of p-phenetidine and acetaminophen by microsomes isolated from rabbit and human kidney. J Pharmacol Exp Ther 1985;235:475-80.
31. Tai HH, Tai CL, Hollander CS. Biosynthesis of prostaglandins in rabbit kidney medulla. Biochem J 1976; 154:257-64.
32. Cavallo T. Fine structural localization of endogenous peroxidase activity in inner medullary interstitial cells of the rat kidney. Lab Invest 1974;31:458-64.
33. Benet LZ, Williams RL. Design and optimization of dosage regimens: pharmacokinetic data. In: Gilman AG, Rall TW, Nies AS, Taylor P, eds. The pharmacological basis of therapeutics. 8th ed. New York: Pergamon Press, 1990:1650-1735.
34. Debruyne D, Ryckelynck JP. Clinical pharmacokinetics of fluconazole. Clin Pharmacokinet 1993;24:10-27.