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Chemical Compound Review

Nizoral     1-[4-[4-[[(2S,4S)-2-(2,4- dichlorophenyl)-2...

Synonyms: Fungoral, Fungarest, Ketoisdin, Xolegel, ketoconazole, ...
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Disease relevance of Nizoral


Psychiatry related information on Nizoral


High impact information on Nizoral


Chemical compound and disease context of Nizoral


Biological context of Nizoral

  • Following continuous oral treatment, the mean day 28 AUC for all-trans RA was significantly lower than that on day 1 (213 ng/mL per hour versus 467 ng/mL per hour; P < .01), a decline significantly attenuated by ketoconazole, which increased the mean plasma all-trans RA AUC on day 29 to 375 ng/mL per hour (P < .01) [20].
  • PURPOSE: We studied the clinical pharmacology of all-trans RA in cancer patients to determine possible mechanisms of acquired resistance and evaluated the potential for reversal by ketoconazole, an inhibitor of cytochrome-P450 oxidative enzymes [20].
  • Ketoconazole-deltanoid combinations produced only minor changes in intracellular calcium homeostasis compared with changes produced by 1,25-dihydroxyvitamin D3, either alone or in combination with ketoconazole [14].
  • CONCLUSIONS: The bioavailability of oral ketoconazole is reduced in patients with AIDS, largely as a result of gastric hypochlorhydria [21].
  • The binding of two molecules of ketoconazole to the CYP3A4 active site and the clear indication of multiple binding modes for erythromycin has implications for the interpretation of the atypical kinetic data often displayed by CYP3A4 [22].

Anatomical context of Nizoral

  • In cultured hepatocytes conversion of [4-14C]cholesterol into bile acids was dose dependently reduced by the antimycotic drug ketoconazole, giving half-maximal inhibition at 10 microM ketoconazole in rat hepatocytes and at 1 microM in human hepatocytes [23].
  • Ketoconazole binds to glucocorticoid receptors and exhibits glucocorticoid antagonist activity in cultured cells [15].
  • When patients who had received allogeneic bone-marrow transplant were studied separately, there was no significant difference between the two treatments, probably because there was a fall-off in ketoconazole absorption from the end of the third week after the transplant [24].
  • The encouraging clinical responses, convenience, safety, and the consistent penetration of ketoconazole into obstructed and nonobstructed cerebrospinal fluid support the use of these regimens as alternatives to conventional therapy [25].
  • High-dose ketoconazole for treatment of fungal infections of the central nervous system [25].

Associations of Nizoral with other chemical compounds


Gene context of Nizoral


Analytical, diagnostic and therapeutic context of Nizoral


  1. Recurrent vulvovaginal candidiasis. A prospective study of the efficacy of maintenance ketoconazole therapy. Sobel, J.D. N. Engl. J. Med. (1986) [Pubmed]
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  3. Candidal epididymitis treated with ketoconazole. Swartz, D.A., Harrington, P., Wilcox, R. N. Engl. J. Med. (1988) [Pubmed]
  4. Ketoconazole to reduce the need for cyclosporine after cardiac transplantation. Keogh, A., Spratt, P., McCosker, C., Macdonald, P., Mundy, J., Kaan, A. N. Engl. J. Med. (1995) [Pubmed]
  5. Reversible adrenal insufficiency induced by ketoconazole. Tucker, W.S., Snell, B.B., Island, D.P., Gregg, C.R. JAMA (1985) [Pubmed]
  6. Late-onset congenital adrenal hyperplasia: a treatable cause of anxiety. Jacobs, A.R., Edelheit, P.B., Coleman, A.E., Herzog, A.G. Biol. Psychiatry (1999) [Pubmed]
  7. Ketoconazole increases cocaine and opioid use in methadone maintained patients. Kosten, T.R., Oliveto, A., Sevarino, K.A., Gonsai, K., Feingold, A. Drug and alcohol dependence. (2002) [Pubmed]
  8. Rapid increase in bone mineral density in a child with osteoporosis and autoimmune hypoparathyroidism treated with PTH 1-34. Koch, C.A. Exp. Clin. Endocrinol. Diabetes (2001) [Pubmed]
  9. New developments in chemotherapy for non-invasive fungal infections. Hossain, M.A., Ghannoum, M.A. Expert opinion on investigational drugs. (2001) [Pubmed]
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  11. Torsades de pointes occurring in association with terfenadine use. Monahan, B.P., Ferguson, C.L., Killeavy, E.S., Lloyd, B.K., Troy, J., Cantilena, L.R. JAMA (1990) [Pubmed]
  12. Disseminated intravascular coagulation in prostatic carcinoma reversed by ketoconazole. Litt, M.R., Bell, W.R., Lepor, H.A. JAMA (1987) [Pubmed]
  13. Failure of ketoconazole in cryptococcal meningitis. Perfect, J.R., Durack, D.T., Hamilton, J.D., Gallis, H.A. JAMA (1982) [Pubmed]
  14. Synergistic induction of HL60 cell differentiation by ketoconazole and 1-desoxy analogues of vitamin D3. Wang, X., Gardner, J.P., Kheir, A., Uskokovic, M.R., Studzinski, G.P. J. Natl. Cancer Inst. (1997) [Pubmed]
  15. Ketoconazole binds to glucocorticoid receptors and exhibits glucocorticoid antagonist activity in cultured cells. Loose, D.S., Stover, E.P., Feldman, D. J. Clin. Invest. (1983) [Pubmed]
  16. Ketoconazole therapy for endemic blastomycosis. Bradsher, R.W., Rice, D.C., Abernathy, R.S. Ann. Intern. Med. (1985) [Pubmed]
  17. Relapse of Candida parapsilosis endocarditis after long-term suppression with flucytosin: retreatment with valve replacement and ketoconazole. Samelson, L.E., Lerner, S.A., Resnekov, L., Anagnostopoulos, C. Ann. Intern. Med. (1980) [Pubmed]
  18. Ketoconazole blocks adrenal steroid synthesis. Pont, A., Williams, P.L., Loose, D.S., Feldman, D., Reitz, R.E., Bochra, C., Stevens, D.A. Ann. Intern. Med. (1982) [Pubmed]
  19. Antiandrogen withdrawal alone or in combination with ketoconazole in androgen-independent prostate cancer patients: a phase III trial (CALGB 9583). Small, E.J., Halabi, S., Dawson, N.A., Stadler, W.M., Rini, B.I., Picus, J., Gable, P., Torti, F.M., Kaplan, E., Vogelzang, N.J. J. Clin. Oncol. (2004) [Pubmed]
  20. Constitutive variability in the pharmacokinetics of the natural retinoid, all-trans-retinoic acid, and its modulation by ketoconazole. Rigas, J.R., Francis, P.A., Muindi, J.R., Kris, M.G., Huselton, C., DeGrazia, F., Orazem, J.P., Young, C.W., Warrell, R.P. J. Natl. Cancer Inst. (1993) [Pubmed]
  21. Gastropathy and ketoconazole malabsorption in the acquired immunodeficiency syndrome (AIDS). Lake-Bakaar, G., Tom, W., Lake-Bakaar, D., Gupta, N., Beidas, S., Elsakr, M., Straus, E. Ann. Intern. Med. (1988) [Pubmed]
  22. From the Cover: Structural basis for ligand promiscuity in cytochrome P450 3A4. Ekroos, M., Sjögren, T. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  23. Ketoconazole blocks bile acid synthesis in hepatocyte monolayer cultures and in vivo in rat by inhibiting cholesterol 7 alpha-hydroxylase. Princen, H.M., Huijsmans, C.M., Kuipers, F., Vonk, R.J., Kempen, H.J. J. Clin. Invest. (1986) [Pubmed]
  24. Ketoconazole versus nystatin plus amphotericin B for fungal prophylaxis in severely immunocompromised patients. Hann, I.M., Prentice, H.G., Corringham, R., Blacklock, H.A., Keaney, M., Shannon, M., Noone, P., Gascoigne, E., Fox, J., Boesen, E., Szawatkowski, M., Hoffbrand, A.V. Lancet (1982) [Pubmed]
  25. High-dose ketoconazole for treatment of fungal infections of the central nervous system. Craven, P.C., Graybill, J.R., Jorgensen, J.H., Dismukes, W.E., Levine, B.E. Ann. Intern. Med. (1983) [Pubmed]
  26. Concomitant administration of cyclosporin and ketoconazole in renal transplant recipients. First, M.R., Schroeder, T.J., Weiskittel, P., Myre, S.A., Alexander, J.W., Pesce, A.J. Lancet (1989) [Pubmed]
  27. Increased gastric pH and the bioavailability of fluconazole and ketoconazole. Blum, R.A., D'Andrea, D.T., Florentino, B.M., Wilton, J.H., Hilligoss, D.M., Gardner, M.J., Henry, E.B., Goldstein, H., Schentag, J.J. Ann. Intern. Med. (1991) [Pubmed]
  28. Fungal peritonitis in patients on continuous ambulatory peritoneal dialysis. Kerr, C.M., Perfect, J.R., Craven, P.C., Jorgensen, J.H., Drutz, D.J., Shelburne, J.D., Gallis, H.A., Gutman, R.A. Ann. Intern. Med. (1983) [Pubmed]
  29. Modulation of arteriolar blood flow by inhibitors of arachidonic acid oxidation after thermal injury: possible role for a novel class of vasodilator metabolites. Proctor, K.G., Shatkin, S., Kaminski, P.M., Falck, J.R., Capdevila, J.H. Circulation (1988) [Pubmed]
  30. Inhibitors of cytochrome P-450 attenuate the myogenic response of dog renal arcuate arteries. Kauser, K., Clark, J.E., Masters, B.S., Ortiz de Montellano, P.R., Ma, Y.H., Harder, D.R., Roman, R.J. Circ. Res. (1991) [Pubmed]
  31. Activated pregnenolone X-receptor is a target for ketoconazole and its analogs. Wang, H., Huang, H., Li, H., Teotico, D.G., Sinz, M., Baker, S.D., Staudinger, J., Kalpana, G., Redinbo, M.R., Mani, S. Clin. Cancer Res. (2007) [Pubmed]
  32. Cytochrome P450 3A inhibition by ketoconazole affects prasugrel and clopidogrel pharmacokinetics and pharmacodynamics differently. Farid, N.A., Payne, C.D., Small, D.S., Winters, K.J., Ernest, C.S., Brandt, J.T., Darstein, C., Jakubowski, J.A., Salazar, D.E. Clin. Pharmacol. Ther. (2007) [Pubmed]
  33. CYP3A5*1/*3 genotype influences the blood concentration of tacrolimus in response to metabolic inhibition by ketoconazole. Chandel, N., Aggarwal, P.K., Minz, M., Sakhuja, V., Kohli, K.K., Jha, V. Pharmacogenet. Genomics (2009) [Pubmed]
  34. Phase II study of androgen synthesis inhibition with ketoconazole, hydrocortisone, and dutasteride in asymptomatic castration-resistant prostate cancer. Taplin, M.E., Regan, M.M., Ko, Y.J., Bubley, G.J., Duggan, S.E., Werner, L., Beer, T.M., Ryan, C.W., Mathew, P., Tu, S.M., Denmeade, S.R., Oh, W.K., Sartor, O., Mantzoros, C.S., Rittmaster, R., Kantoff, P.W., Balk, S.P. Clin. Cancer Res. (2009) [Pubmed]
  35. A novel human cytochrome P450, CYP26C1, involved in metabolism of 9-cis and all-trans isomers of retinoic acid. Taimi, M., Helvig, C., Wisniewski, J., Ramshaw, H., White, J., Amad, M., Korczak, B., Petkovich, M. J. Biol. Chem. (2004) [Pubmed]
  36. Metabolism of irinotecan (CPT-11) by CYP3A4 and CYP3A5 in humans. Santos, A., Zanetta, S., Cresteil, T., Deroussent, A., Pein, F., Raymond, E., Vernillet, L., Risse, M.L., Boige, V., Gouyette, A., Vassal, G. Clin. Cancer Res. (2000) [Pubmed]
  37. Effects of ketoconazole on glucuronidation by UDP-glucuronosyltransferase enzymes. Yong, W.P., Ramirez, J., Innocenti, F., Ratain, M.J. Clin. Cancer Res. (2005) [Pubmed]
  38. Ketoconazole and miconazole are antagonists of the human glucocorticoid receptor: consequences on the expression and function of the constitutive androstane receptor and the pregnane X receptor. Duret, C., Daujat-Chavanieu, M., Pascussi, J.M., Pichard-Garcia, L., Balaguer, P., Fabre, J.M., Vilarem, M.J., Maurel, P., Gerbal-Chaloin, S. Mol. Pharmacol. (2006) [Pubmed]
  39. Acute hypoadrenalism and hepatotoxicity after treatment with ketoconazole. McCance, D.R., Ritchie, C.M., Sheridan, B., Atkinson, A.B. Lancet (1987) [Pubmed]
  40. Modified response to ketoconazole of Candida albicans from a treatment failure. Warnock, D.W., Johnson, E.M., Richardson, M.D., Vickers, C.F. Lancet (1983) [Pubmed]
  41. Ketoconazole and fungal CAPD peritonitis. Chapman, J.R., Warnock, D.W. Lancet (1983) [Pubmed]
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