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Chemical Compound Review

Diflucan     2-(2,4-difluorophenyl)-1,3- bis(1,2,4...

Synonyms: Flunazul, Afungil, FlucoLich, Flucobeta, Fungata, ...
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Disease relevance of Fungata

  • Fluconazole taken prophylactically reduces the frequency of cryptococcosis, esophageal candidiasis, and superficial fungal infections in HIV-infected patients, especially those with 50 or fewer CD4+ lymphocytes per cubic millimeter, but the drug does not reduce overall mortality [1].
  • Amphotericin versus fluconazole in cryptococcal meningitis [2].
  • There was no significant difference between the groups in overall mortality due to cryptococcosis (amphotericin vs. fluconazole, 9 of 63 [14 percent] vs. 24 of 131 [18 percent]; P = 0.48); however, mortality during the first two weeks of therapy was higher in the fluconazole group (15 percent vs. 8 percent; P = 0.25) [3].
  • Fluconazole or placebo was administered prophylactically from the start of the conditioning regimen until the neutrophil count returned to 1000 per microliter, toxicity was suspected, or a systemic fungal infection was suspected or proved [4].
  • Fluconazole and Candida krusei fungemia [5].

Psychiatry related information on Fungata


High impact information on Fungata

  • Mutations of POR also affect drug-metabolizing P450 enzymes, explaining the association of ABS with maternal fluconazole ingestion [11].
  • Invasive fungal infection with positive growth of fungal isolates from the blood, urine, or cerebrospinal fluid developed in 10 infants in the placebo group (20 percent) and none of the infants in the fluconazole group (difference in risk, 0.20; 95 percent confidence interval, 0.04 to 0.36; P=0.008) [12].
  • RESULTS: The 50 infants randomly assigned to fluconazole and the 50 control infants were similar in terms of birth weight, gestational age at birth, and base-line risk factors for fungal infection [12].
  • Seventy-two percent of the 151 fluconazole recipients and 60 percent of the 155 itraconazole recipients had negative cultures at 10 weeks (95 percent confidence interval for the difference in percentages, -100 to 21) [13].
  • There was no statistically significant difference in outcome: of the 103 patients treated with amphotericin B, 81 (79 percent) were judged to have been treated successfully, as were 72 of the 103 patients treated with fluconazole (70 percent P = 0.22; 95 percent confidence interval for the difference, -5 to 23 percent) [14].

Chemical compound and disease context of Fungata


Biological context of Fungata


Anatomical context of Fungata

  • Prophylactic administration of fluconazole to recipients of bone marrow transplants reduces the incidence of both systemic and superficial fungal infections [4].
  • Among the three, fluconazole has the most attractive pharmacologic profile, including the capacity to produce high concentrations of active drug in cerebrospinal fluid and urine [15].
  • In contrast, KGF receptor transcripts were localized to the cryptal region of the mucosal epithelium in both normal and IBD tissue, with no apparent differences in the level of expression [23].
  • Computer analysis of the X-ray spectra allowed elemental microanalysis of the nucleus, cytoplasm, and mitotic chromatin regions in the cryptal and villus enterocytes [24].
  • The HFE protein was shown by immunohistochemistry to be expressed in certain epithelial cells throughout the human alimentary tract and to have a unique localization in the cryptal cells of small intestine, where signals to regulate iron absorption are received from the body [25].

Associations of Fungata with other chemical compounds

  • There was a difference of 19 percent in the estimated probability of remaining relapse-free at one year between the fluconazole group (97 percent) and the amphotericin B group (78 percent) (95 percent confidence interval, 7 percent to 31 percent; P less than 0.001) [26].
  • In multivariate analyses, the best predictors of recurrence-free survival were fluconazole treatment (P = 0.02; relative hazard, 13.2), a lower serum cryptococcal-antigen titer (P = 0.05; relative hazard, 1.2), and more prolonged primary therapy with flucytosine (P = 0.09; relative hazard, 1.1) [27].
  • The epithelial surface pH was 7.13 +/- 0.08 at the apex of mucosal villus and 7.42 +/- 0.11 (n = 5) in the cryptal area between the villi, i.e., greater than 1 pH unit higher than that of the luminal bulk solution (pH 6), thus suggesting active alkalization of the epithelial surface [28].
  • In vitro susceptibility tests to fluconazole and ketoconazole were also performed [29].
  • First, CRZ1 was not involved in tolerance to antifungal agents (fluconazole, terbinafine) on the opposite to calcineurin [30].

Gene context of Fungata


Analytical, diagnostic and therapeutic context of Fungata


  1. A randomized trial comparing fluconazole with clotrimazole troches for the prevention of fungal infections in patients with advanced human immunodeficiency virus infection. NIAID AIDS Clinical Trials Group. Powderly, W.G., Finkelstein, D., Feinberg, J., Frame, P., He, W., van der Horst, C., Koletar, S.L., Eyster, M.E., Carey, J., Waskin, H. N. Engl. J. Med. (1995) [Pubmed]
  2. Amphotericin versus fluconazole in cryptococcal meningitis. Tolins, J.P. N. Engl. J. Med. (1992) [Pubmed]
  3. Comparison of amphotericin B with fluconazole in the treatment of acute AIDS-associated cryptococcal meningitis. The NIAID Mycoses Study Group and the AIDS Clinical Trials Group. Saag, M.S., Powderly, W.G., Cloud, G.A., Robinson, P., Grieco, M.H., Sharkey, P.K., Thompson, S.E., Sugar, A.M., Tuazon, C.U., Fisher, J.F. N. Engl. J. Med. (1992) [Pubmed]
  4. A controlled trial of fluconazole to prevent fungal infections in patients undergoing bone marrow transplantation. Goodman, J.L., Winston, D.J., Greenfield, R.A., Chandrasekar, P.H., Fox, B., Kaizer, H., Shadduck, R.K., Shea, T.C., Stiff, P., Friedman, D.J. N. Engl. J. Med. (1992) [Pubmed]
  5. Fluconazole and Candida krusei fungemia. Persons, D.A., Laughlin, M., Tanner, D., Perfect, J., Gockerman, J.P., Hathorn, J.W. N. Engl. J. Med. (1991) [Pubmed]
  6. Cyclophosphamide metabolism is affected by azole antifungals. Marr, K.A., Leisenring, W., Crippa, F., Slattery, J.T., Corey, L., Boeckh, M., McDonald, G.B. Blood (2004) [Pubmed]
  7. Risk factors associated with Epstein-Barr virus replication in oral epithelial cells of HIV-infected individuals. Boulter, A.W., Soltanpoor, N., Swan, A.V., Birnbaum, W., Johnson, N.W., Teo, C.G. AIDS (1996) [Pubmed]
  8. Electronic compliance assessment of antifungal prophylaxis for human immunodeficiency virus-infected women. Geletko, S.M., Segarra, M., Mayer, K.H., Fiore, T.C., Bettencourt, F.A., Flanigan, T.P., Dudley, M.N. Antimicrob. Agents Chemother. (1996) [Pubmed]
  9. Antifungal agents for preventing fungal infections in non-neutropenic critically ill and surgical patients: systematic review and meta-analysis of randomized clinical trials. Playford, E.G., Webster, A.C., Sorrell, T.C., Craig, J.C. J. Antimicrob. Chemother. (2006) [Pubmed]
  10. The effect of fluconazole prophylaxis on fungal colonization in neutropenic cancer patients. Bone Marrow Transplantation Team. Chandrasekar, P.H., Gatny, C.M. J. Antimicrob. Chemother. (1994) [Pubmed]
  11. Mutant P450 oxidoreductase causes disordered steroidogenesis with and without Antley-Bixler syndrome. Flück, C.E., Tajima, T., Pandey, A.V., Arlt, W., Okuhara, K., Verge, C.F., Jabs, E.W., Mendonça, B.B., Fujieda, K., Miller, W.L. Nat. Genet. (2004) [Pubmed]
  12. Fluconazole prophylaxis against fungal colonization and infection in preterm infants. Kaufman, D., Boyle, R., Hazen, K.C., Patrie, J.T., Robinson, M., Donowitz, L.G. N. Engl. J. Med. (2001) [Pubmed]
  13. Treatment of cryptococcal meningitis associated with the acquired immunodeficiency syndrome. National Institute of Allergy and Infectious Diseases Mycoses Study Group and AIDS Clinical Trials Group. van der Horst, C.M., Saag, M.S., Cloud, G.A., Hamill, R.J., Graybill, J.R., Sobel, J.D., Johnson, P.C., Tuazon, C.U., Kerkering, T., Moskovitz, B.L., Powderly, W.G., Dismukes, W.E. N. Engl. J. Med. (1997) [Pubmed]
  14. A randomized trial comparing fluconazole with amphotericin B for the treatment of candidemia in patients without neutropenia. Candidemia Study Group and the National Institute. Rex, J.H., Bennett, J.E., Sugar, A.M., Pappas, P.G., van der Horst, C.M., Edwards, J.E., Washburn, R.G., Scheld, W.M., Karchmer, A.W., Dine, A.P. N. Engl. J. Med. (1994) [Pubmed]
  15. Oral azole drugs as systemic antifungal therapy. Como, J.A., Dismukes, W.E. N. Engl. J. Med. (1994) [Pubmed]
  16. Comparison of fluconazole and ketoconazole for oropharyngeal candidiasis in AIDS. De Wit, S., Weerts, D., Goossens, H., Clumeck, N. Lancet (1989) [Pubmed]
  17. Fluconazole compared with amphotericin B plus flucytosine for cryptococcal meningitis in AIDS. A randomized trial. Larsen, R.A., Leal, M.A., Chan, L.S. Ann. Intern. Med. (1990) [Pubmed]
  18. Calcineurin is essential for survival during membrane stress in Candida albicans. Cruz, M.C., Goldstein, A.L., Blankenship, J.R., Del Poeta, M., Davis, D., Cardenas, M.E., Perfect, J.R., McCusker, J.H., Heitman, J. EMBO J. (2002) [Pubmed]
  19. Element concentration changes in mitotically active and postmitotic enterocytes. An x-ray microanalysis study. Cameron, I.L., Smith, N.K., Pool, T.B. J. Cell Biol. (1979) [Pubmed]
  20. Increased plasma rifabutin levels with concomitant fluconazole therapy in HIV-infected patients. Trapnell, C.B., Narang, P.K., Li, R., Lavelle, J.P. Ann. Intern. Med. (1996) [Pubmed]
  21. Population genomics of drug resistance in Candida albicans. Cowen, L.E., Nantel, A., Whiteway, M.S., Thomas, D.Y., Tessier, D.C., Kohn, L.M., Anderson, J.B. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  22. Age-related hypermethylation of the 5' region of MLH1 in normal colonic mucosa is associated with microsatellite-unstable colorectal cancer development. Nakagawa, H., Nuovo, G.J., Zervos, E.E., Martin, E.W., Salovaara, R., Aaltonen, L.A., de la Chapelle, A. Cancer Res. (2001) [Pubmed]
  23. Increased expression of keratinocyte growth factor messenger RNA associated with inflammatory bowel disease. Finch, P.W., Pricolo, V., Wu, A., Finkelstein, S.D. Gastroenterology (1996) [Pubmed]
  24. Concentration of elements in mitotic chromatin as measured by x-ray microanalysis. Cameron, I.L., Sparks, R.L., Horn, K.L., Smith, N.R. J. Cell Biol. (1977) [Pubmed]
  25. Association of the transferrin receptor in human placenta with HFE, the protein defective in hereditary hemochromatosis. Parkkila, S., Waheed, A., Britton, R.S., Bacon, B.R., Zhou, X.Y., Tomatsu, S., Fleming, R.E., Sly, W.S. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  26. A controlled trial of fluconazole or amphotericin B to prevent relapse of cryptococcal meningitis in patients with the acquired immunodeficiency syndrome. The NIAID AIDS Clinical Trials Group and Mycoses Study Group. Powderly, W.G., Saag, M.S., Cloud, G.A., Robinson, P., Meyer, R.D., Jacobson, J.M., Graybill, J.R., Sugar, A.M., McAuliffe, V.J., Follansbee, S.E. N. Engl. J. Med. (1992) [Pubmed]
  27. A placebo-controlled trial of maintenance therapy with fluconazole after treatment of cryptococcal meningitis in the acquired immunodeficiency syndrome. California Collaborative Treatment Group. Bozzette, S.A., Larsen, R.A., Chiu, J., Leal, M.A., Jacobsen, J., Rothman, P., Robinson, P., Gilbert, G., McCutchan, J.A., Tilles, J. N. Engl. J. Med. (1991) [Pubmed]
  28. Intracellular pH in isolated Necturus duodenal mucosa exposed to luminal acid. Paimela, H., Kiviluoto, T., Mustonen, H., Kivilaakso, E. Gastroenterology (1992) [Pubmed]
  29. Change in fluconazole susceptibility patterns and genetic relationship among oral Candida albicans isolates. Diaz-Guerra, T.M., Martinez-Suarez, J.V., Laguna, F., Valencia, E., Rodriguez-Tudela, J.L. AIDS (1998) [Pubmed]
  30. CRZ1, a target of the calcineurin pathway in Candida albicans. Karababa, M., Valentino, E., Pardini, G., Coste, A.T., Bille, J., Sanglard, D. Mol. Microbiol. (2006) [Pubmed]
  31. Pdr1 regulates multidrug resistance in Candida glabrata: gene disruption and genome-wide expression studies. Vermitsky, J.P., Earhart, K.D., Smith, W.L., Homayouni, R., Edlind, T.D., Rogers, P.D. Mol. Microbiol. (2006) [Pubmed]
  32. Regulation of azole drug susceptibility by Candida albicans protein kinase CK2. Bruno, V.M., Mitchell, A.P. Mol. Microbiol. (2005) [Pubmed]
  33. 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]
  34. Effects of the antifungal agents on oxidative drug metabolism: clinical relevance. Venkatakrishnan, K., von Moltke, L.L., Greenblatt, D.J. Clinical pharmacokinetics. (2000) [Pubmed]
  35. Characterization of a lanosterol 14 alpha-demethylase from Pneumocystis carinii. Morales, I.J., Vohra, P.K., Puri, V., Kottom, T.J., Limper, A.H., Thomas, C.F. Am. J. Respir. Cell Mol. Biol. (2003) [Pubmed]
  36. Prophylactic fluconazole and marrow transplantation. Scholten, S.L., Nettleman, M.D., Sarrazin, E.F. N. Engl. J. Med. (1992) [Pubmed]
  37. Problems in the design and reporting of trials of antifungal agents encountered during meta-analysis. Johansen, H.K., Gotzsche, P.C. JAMA (1999) [Pubmed]
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