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Chemical Compound Review

Dactarin     1-[2-(2,4-dichlorophenyl)-2- [(2,4...

Synonyms: Daktarin, Micozole, Monistat, Brentan, Miconazol, ...
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Disease relevance of miconazole


Psychiatry related information on miconazole


High impact information on miconazole


Chemical compound and disease context of miconazole


Biological context of miconazole


Anatomical context of miconazole


Associations of miconazole with other chemical compounds

  • Both 17-ODYA and miconazole (10(-5) mol/L, a chemically distinct P450 inhibitor) further reduced the dilation to AA in the presence of INDO [27].
  • Clotrimazole and miconazole were also strong inhibitors of P450 3A-mediated activities in contrast to the other imidazole derivatives [28].
  • The transcription rates of mEH mRNA at 24 hr were significantly less than those observed at 12 hr after a single treatment with either ketoconazole, miconazole, or econazole, resulting in 6.5-, 2.5-, and 2-fold increases, respectively, relative to control [29].
  • In the current study, we investigated the effect of ketoconazole and other azole-derived drugs, miconazole and fluconazole, on the transcriptional activity of the human GR (hGR) in HeLa and HepG2 cells, and in primary human hepatocytes [30].
  • RESULTS: Glutamate treatment (100 mumol/L for 30 minutes) induced a threefold increase in the formation of EETs from [14C]AA by cultured astrocytes, and the increase was inhibited by miconazole (20 mumol/L), an inhibitor of P-450 AA epoxygenase [26].
  • In rat liver microsomes in vitro, defluorination of 18F-FCWAY was almost completely inhibited by miconazole and, to a less extent, by diclofenac [31].
  • With respect to the antifungal activity of miconazole, we demonstrate an antagonism with tryptophan and a synergy with a yeast endocytosis inhibitor [32].

Gene context of miconazole


Analytical, diagnostic and therapeutic context of miconazole


  1. Disseminated candidiasis in a patient with acute leukemia. Successful treatment with miconazole. Katz, M.E., Cassileth, P.A. JAMA (1977) [Pubmed]
  2. Treatment of coccidioidomycosis with miconazole. Hoeprich, P.D., Lawrence, R.M., Goldstein, E. JAMA (1980) [Pubmed]
  3. Miconazole in paracoccidioidomycosis. Stevens, D.A., Restrepo, A. Lancet (1979) [Pubmed]
  4. Miconazole in fungal endophthalmitis. Gallo, J., Grunstein, H., Clifton-Bligh, P., Billson, F.A., Tarr, K.H. Lancet (1982) [Pubmed]
  5. Cardiorespiratory toxicity due to miconazole. Fainstein, V., Bodey, G.P. Ann. Intern. Med. (1980) [Pubmed]
  6. Anomalous effect of subconjunctival miconazole on Candida albicans keratitis in rabbits. O'Day, D.M., Head, W.S., Robinson, R.D., Williams, T.E., Gedde, S.J. Am. J. Ophthalmol. (1991) [Pubmed]
  7. Chemoprophylaxis of fungal deterioration of the Provox silicone tracheoesophageal prosthesis in postlaryngectomy patients. van Weissenbruch, R., Bouckaert, S., Remon, J.P., Nelis, H.J., Aerts, R., Albers, F.W. The Annals of otology, rhinology, and laryngology. (1997) [Pubmed]
  8. Systemic corticosteroid therapy of oral vesiculoerosive diseases (OVED). An open trial. Carbone, M., Carrozzo, M., Castellano, S., Conrotto, D., Broccoletti, R., Gandolfo, S. Minerva stomatologica. (1998) [Pubmed]
  9. Treatment of funguria. Wong-Beringer, A., Jacobs, R.A., Guglielmo, B.J. JAMA (1992) [Pubmed]
  10. A case of chronic oropharyngo-esophageal candidiasis with immunological deficiency: successful treatment with miconazole. Tytgat, G.N., Surachno, S., de Groot, W.P., Schellekens, P.T. Gastroenterology (1977) [Pubmed]
  11. Miconazole in cryptococcosis and systemic candidiasis: a word of caution. Bennett, J.E., Remington, J.S. Ann. Intern. Med. (1981) [Pubmed]
  12. Successful treatment of cerebral cryptococcoma and meningitis with miconazole. Weinstein, L., Jacoby, I. Ann. Intern. Med. (1980) [Pubmed]
  13. Infection of B lymphocytes by a human herpesvirus, Epstein-Barr virus, is blocked by calmodulin antagonists. Nemerow, G.R., Cooper, N.R. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  14. Imidazole antifungals Miconazole and Econazole induce apoptosis in mouse lymphoma and human T cell leukemia cells: regulation by Bcl-2 and potential role of calcium. Sobecks, R., McCormick, T.S., Distelhorst, C.W. Cell Death Differ. (1996) [Pubmed]
  15. Pseudallescheria boydii brain abscess: association with near-drowning and efficacy of high-dose, prolonged miconazole therapy in patients with multiple abscesses. Dworzack, D.L., Clark, R.B., Borkowski, W.J., Smith, D.L., Dykstra, M., Pugsley, M.P., Horowitz, E.A., Connolly, T.L., McKinney, D.L., Hostetler, M.K. Medicine (Baltimore) (1989) [Pubmed]
  16. Toxicity of amphotericin B, miconazole, and ketoconazole to human granulocyte progenitor cells in vitro. Meeker, T.C., Siegel, M.S., Shiota, F.M., Crowley, J.J., McGuffin, R.W. Antimicrob. Agents Chemother. (1983) [Pubmed]
  17. Failure of 2-deoxy-D-glucose in the treatment of experimental cutaneous and genital infections due to herpes simplex virus. Kern, E.R., Glasgow, L.A., Klein, R.J., Friedman-Kien, A.E. J. Infect. Dis. (1982) [Pubmed]
  18. High affinity inhibition of Ca(2+)-dependent K+ channels by cytochrome P-450 inhibitors. Alvarez, J., Montero, M., Garcia-Sancho, J. J. Biol. Chem. (1992) [Pubmed]
  19. Mechanisms of the stereoselective interaction between miconazole and racemic warfarin in human subjects. O'Reilly, R.A., Goulart, D.A., Kunze, K.L., Neal, J., Gibaldi, M., Eddy, A.C., Trager, W.F. Clin. Pharmacol. Ther. (1992) [Pubmed]
  20. In vivo pharmacokinetics and pharmacodynamics of topical ketoconazole and miconazole in human stratum corneum. Pershing, L.K., Corlett, J., Jorgensen, C. Antimicrob. Agents Chemother. (1994) [Pubmed]
  21. Clinically important drug interactions with anticoagulants. An update. Harder, S., Thürmann, P. Clinical pharmacokinetics. (1996) [Pubmed]
  22. Identification of epoxyeicosatrienoic acids as endothelium-derived hyperpolarizing factors. Campbell, W.B., Gebremedhin, D., Pratt, P.F., Harder, D.R. Circ. Res. (1996) [Pubmed]
  23. Metabolism of N-hydroxy-2-acetylaminofluorene and N-hydroxy-2-aminofluorene by guinea pig liver microsomes. Razzouk, C., Batardy-Grégoire, M., Roberfroid, M. Cancer Res. (1982) [Pubmed]
  24. Differential effect of imidazole antibiotics on untransformed and virus-transformed rat cell lines. Kuwano, M., Akiyama, S., Kaneko, M., Ikezaki, K., Takaki, R., Kimura, G. Cancer Res. (1982) [Pubmed]
  25. Molecular characterization of an arachidonic acid epoxygenase in rat brain astrocytes. Alkayed, N.J., Narayanan, J., Gebremedhin, D., Medhora, M., Roman, R.J., Harder, D.R. Stroke (1996) [Pubmed]
  26. Role of P-450 arachidonic acid epoxygenase in the response of cerebral blood flow to glutamate in rats. Alkayed, N.J., Birks, E.K., Narayanan, J., Petrie, K.A., Kohler-Cabot, A.E., Harder, D.R. Stroke (1997) [Pubmed]
  27. Human coronary arteriolar dilation to arachidonic acid depends on cytochrome P-450 monooxygenase and Ca2+-activated K+ channels. Miura, H., Gutterman, D.D. Circ. Res. (1998) [Pubmed]
  28. Effects of imidazole derivatives on cytochromes P450 from human hepatocytes in primary culture. Maurice, M., Pichard, L., Daujat, M., Fabre, I., Joyeux, H., Domergue, J., Maurel, P. FASEB J. (1992) [Pubmed]
  29. Transcriptional regulation of rat microsomal epoxide hydrolase gene by imidazole antimycotic agents. Kim, S.G. Mol. Pharmacol. (1992) [Pubmed]
  30. 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]
  31. PET imaging of brain 5-HT1A receptors in rat in vivo with 18F-FCWAY and improvement by successful inhibition of radioligand defluorination with miconazole. Tipre, D.N., Zoghbi, S.S., Liow, J.S., Green, M.V., Seidel, J., Ichise, M., Innis, R.B., Pike, V.W. J. Nucl. Med. (2006) [Pubmed]
  32. Miconazole induces changes in actin cytoskeleton prior to reactive oxygen species induction in yeast. Thevissen, K., Ayscough, K.R., Aerts, A.M., Du, W., De Brucker, K., Meert, E.M., Ausma, J., Borgers, M., Cammue, B.P., François, I.E. J. Biol. Chem. (2007) [Pubmed]
  33. Effects of the antifungal agents on oxidative drug metabolism: clinical relevance. Venkatakrishnan, K., von Moltke, L.L., Greenblatt, D.J. Clinical pharmacokinetics. (2000) [Pubmed]
  34. Detection of a new N-oxidized metabolite of flutamide, N-[4-nitro-3-(trifluoromethyl)phenyl]hydroxylamine, in human liver microsomes and urine of prostate cancer patients. Goda, R., Nagai, D., Akiyama, Y., Nishikawa, K., Ikemoto, I., Aizawa, Y., Nagata, K., Yamazoe, Y. Drug Metab. Dispos. (2006) [Pubmed]
  35. Effect of micafungin on cytochrome P450 3A4 and multidrug resistance protein 1 activities, and its comparison with azole antifungal drugs. Sakaeda, T., Iwaki, K., Kakumoto, M., Nishikawa, M., Niwa, T., Jin, J.S., Nakamura, T., Nishiguchi, K., Okamura, N., Okumura, K. J. Pharm. Pharmacol. (2005) [Pubmed]
  36. Effect of antifungal drugs on cytochrome P450 (CYP) 1A2, CYP2D6, and CYP2E1 activities in human liver microsomes. Niwa, T., Inoue-Yamamoto, S., Shiraga, T., Takagi, A. Biol. Pharm. Bull. (2005) [Pubmed]
  37. ABC transporters Cdr1p, Cdr2p and Cdr3p of a human pathogen Candida albicans are general phospholipid translocators. Smriti, n.u.l.l., Krishnamurthy, S., Dixit, B.L., Gupta, C.M., Milewski, S., Prasad, R. Yeast (2002) [Pubmed]
  38. A cost analysis of topical drug regimens for dermatophyte infections. Chren, M.M., Landefeld, C.S. JAMA (1994) [Pubmed]
  39. Miconazole treatment after renal transplantation. Lai, K.N., Newton, M., Seymour, A., Pugsley, D., Jones, T. Lancet (1981) [Pubmed]
  40. Prevention of fungal sepsis in patients with prolonged neutropenia: a randomized, double-blind, placebo-controlled trial of intravenous miconazole. Wingard, J.R., Vaughan, W.P., Braine, H.G., Merz, W.G., Saral, R. Am. J. Med. (1987) [Pubmed]
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