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Chemical Compound Review

Triazole     2H-triazole

Synonyms: triazol, Osotriazole, V-triazole, SureCN102, SureCN83260, ...
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Disease relevance of Osotriazole

  • The alternative is lifelong treatment with azoles; this appears to be acceptable, because toxicity is uncommon with triazole therapy, even long-term triazole therapy [1].
  • Brassinazole, a synthetic chemical developed in our laboratory, is a triazole-type brassinosteroid biosynthesis inhibitor that induces dwarfism in various plant species [2].
  • We present here the crystal structure of Mycobacterium tuberculosis cytochrome P450 CYP121 in complex with the triazole drug fluconazole, revealing a new azole heme ligation mode [3].
  • We studied the efficacy of itraconazole, a new oral triazole, in 33 patients (32 were immunocompromised) with cryptococcosis [4].
  • A dose comparison study of a new triazole antifungal (D0870) in HIV-positive patients with oral candidiasis [5].

Psychiatry related information on Osotriazole


High impact information on Osotriazole


Chemical compound and disease context of Osotriazole


Biological context of Osotriazole

  • The inhibitors bind in the active site with the N1 and N2 atoms of the triazole moiety complexing two divalent ions [18].
  • The pharmacokinetics and distribution in tissue of several novel triazole antifungal agents were studied in different animal species in order to select an appropriate lead compound [19].
  • When the mutated cyp51A genes were introduced into an A. fumigatus wild-type strain, the transformants exhibited reduced susceptibility to all triazole agents, confirming that the mutations were responsible for the resistance phenotype [20].
  • Regarding itraconazole kinetics, ceftriaxone was shown to alter the disposition of the triazole [21].
  • Further analyses from these in vivo studies have demonstrated that a triazole free drug 24-h AUC/MIC of 20 to 25 is predictive of treatment success [22].

Anatomical context of Osotriazole


Associations of Osotriazole with other chemical compounds


Gene context of Osotriazole


Analytical, diagnostic and therapeutic context of Osotriazole


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  2. Selective interaction of triazole derivatives with DWF4, a cytochrome P450 monooxygenase of the brassinosteroid biosynthetic pathway, correlates with brassinosteroid deficiency in planta. Asami, T., Mizutani, M., Fujioka, S., Goda, H., Min, Y.K., Shimada, Y., Nakano, T., Takatsuto, S., Matsuyama, T., Nagata, N., Sakata, K., Yoshida, S. J. Biol. Chem. (2001) [Pubmed]
  3. Crystal structure of the Mycobacterium tuberculosis P450 CYP121-fluconazole complex reveals new azole drug-P450 binding mode. Seward, H.E., Roujeinikova, A., McLean, K.J., Munro, A.W., Leys, D. J. Biol. Chem. (2006) [Pubmed]
  4. Itraconazole therapy for cryptococcal meningitis and cryptococcosis. Denning, D.W., Tucker, R.M., Hanson, L.H., Hamilton, J.R., Stevens, D.A. Arch. Intern. Med. (1989) [Pubmed]
  5. A dose comparison study of a new triazole antifungal (D0870) in HIV-positive patients with oral candidiasis. De Wit, S., Dupont, B., Cartledge, J.D., Hawkins, D.A., Gazzard, B.G., Clumeck, N., Denning, D.W. AIDS (1997) [Pubmed]
  6. Triadimefon, a triazole fungicide, induces stereotyped behavior and alters monoamine metabolism in rats. Walker, Q.D., Lewis, M.H., Crofton, K.M., Mailman, R.B. Toxicol. Appl. Pharmacol. (1990) [Pubmed]
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  9. Fusarium, a significant emerging pathogen in patients with hematologic malignancy: ten years' experience at a cancer center and implications for management. Boutati, E.I., Anaissie, E.J. Blood (1997) [Pubmed]
  10. Importance of catalase in the disposal of hydrogen peroxide within human erythrocytes. Gaetani, G.F., Kirkman, H.N., Mangerini, R., Ferraris, A.M. Blood (1994) [Pubmed]
  11. Promotion of proton conduction in polymer electrolyte membranes by 1H-1,2,3-triazole. Zhou, Z., Li, S., Zhang, Y., Liu, M., Li, W. J. Am. Chem. Soc. (2005) [Pubmed]
  12. In situ click chemistry: enzyme inhibitors made to their own specifications. Manetsch, R., Krasiński, A., Radić, Z., Raushel, J., Taylor, P., Sharpless, K.B., Kolb, H.C. J. Am. Chem. Soc. (2004) [Pubmed]
  13. Efficacy of voriconazole in treatment of murine pulmonary blastomycosis. Sugar, A.M., Liu, X.P. Antimicrob. Agents Chemother. (2001) [Pubmed]
  14. Effects of age, gender, and race/ethnicity on the pharmacokinetics of posaconazole in healthy volunteers. Sansone-Parsons, A., Krishna, G., Simon, J., Soni, P., Kantesaria, B., Herron, J., Stoltz, R. Antimicrob. Agents Chemother. (2007) [Pubmed]
  15. Efficacies of two new antifungal agents, the triazole ravuconazole and the echinocandin LY-303366, in an experimental model of invasive aspergillosis. Roberts, J., Schock, K., Marino, S., Andriole, V.T. Antimicrob. Agents Chemother. (2000) [Pubmed]
  16. Activity of the triazole SCH 56592 against disseminated murine coccidioidomycosis. Lutz, J.E., Clemons, K.V., Aristizabal, B.H., Stevens, D.A. Antimicrob. Agents Chemother. (1997) [Pubmed]
  17. Treatment of disseminated Torulopsis glabrata infection with DO870 and amphotericin B. Atkinson, B.A., Bocanegra, R., Colombo, A.L., Graybill, J.R. Antimicrob. Agents Chemother. (1994) [Pubmed]
  18. The 1.15A crystal structure of the Staphylococcus aureus methionyl-aminopeptidase and complexes with triazole based inhibitors. Oefner, C., Douangamath, A., D'Arcy, A., Häfeli, S., Mareque, D., Mac Sweeney, A., Padilla, J., Pierau, S., Schulz, H., Thormann, M., Wadman, S., Dale, G.E. J. Mol. Biol. (2003) [Pubmed]
  19. Interspecies comparison of pharmacokinetics of the novel triazole antifungal agent SYN-2869 and its derivatives. Khan, J.K., Montaseri, H., Poglod, M., Bu, H.Z., Zuo, Z., Salama, S.M., Daneshtalab, M., Micetich, R.G. Antimicrob. Agents Chemother. (2000) [Pubmed]
  20. Substitutions at methionine 220 in the 14alpha-sterol demethylase (Cyp51A) of Aspergillus fumigatus are responsible for resistance in vitro to azole antifungal drugs. Mellado, E., Garcia-Effron, G., Alcazar-Fuoli, L., Cuenca-Estrella, M., Rodriguez-Tudela, J.L. Antimicrob. Agents Chemother. (2004) [Pubmed]
  21. Pharmacokinetic interaction between itraconazole and ceftriaxone in Yucatan miniature pigs. Cavalier, A., Levêque, D., Peter, J.D., Salmon, J., Elkhaïli, H., Salmon, Y., Nobelis, P., Geisert, J., Monteil, H., Jehl, F. Antimicrob. Agents Chemother. (1997) [Pubmed]
  22. In vivo pharmacokinetics and pharmacodynamics of a new triazole, voriconazole, in a murine candidiasis model. Andes, D., Marchillo, K., Stamstad, T., Conklin, R. Antimicrob. Agents Chemother. (2003) [Pubmed]
  23. Cytochrome P-450-dependent 14 alpha-demethylation of lanosterol in Candida albicans. Hitchcock, C.A., Brown, S.B., Evans, E.G., Adams, D.J. Biochem. J. (1989) [Pubmed]
  24. Penetration of SCH-39304, a new antifungal triazole, into cerebrospinal fluid of primates. Walsh, T.J., Lester-McCully, C., Rinaldi, M.G., Wallace, J.E., Balis, F.M., Lee, J.W., Pizzo, P.A., Poplack, D.G. Antimicrob. Agents Chemother. (1990) [Pubmed]
  25. Activity of voriconazole, a new triazole, combined with neutrophils or monocytes against Candida albicans: effect of granulocyte colony-stimulating factor and granulocyte-macrophage colony-stimulating factor. Vora, S., Purimetla, N., Brummer, E., Stevens, D.A. Antimicrob. Agents Chemother. (1998) [Pubmed]
  26. Attenuation of itraconazole fungicidal activity following preexposure of Aspergillus fumigatus to fluconazole. Liu, W., Lionakis, M.S., Lewis, R.E., Wiederhold, N., May, G.S., Kontoyiannis, D.P. Antimicrob. Agents Chemother. (2003) [Pubmed]
  27. 5-Aryl-3-(alkylthio)-4H-1,2,4-triazoles as selective antagonists of strychnine-induced convulsions and potential antispastic agents. Kane, J.M., Staeger, M.A., Dalton, C.R., Miller, F.P., Dudley, M.W., Ogden, A.M., Kehne, J.H., Ketteler, H.J., McCloskey, T.C., Senyah, Y. J. Med. Chem. (1994) [Pubmed]
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  30. Impact of antimicrobial dosing regimen on evolution of drug resistance in vivo: fluconazole and Candida albicans. Andes, D., Forrest, A., Lepak, A., Nett, J., Marchillo, K., Lincoln, L. Antimicrob. Agents Chemother. (2006) [Pubmed]
  31. Variability of voriconazole plasma levels measured by new high-performance liquid chromatography and bioassay methods. Pascual, A., Nieth, V., Calandra, T., Bille, J., Bolay, S., Decosterd, L.A., Buclin, T., Majcherczyk, P.A., Sanglard, D., Marchetti, O. Antimicrob. Agents Chemother. (2007) [Pubmed]
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  33. Histamine H2-receptor antagonists have no clinically significant effect on the steady-state pharmacokinetics of voriconazole. Purkins, L., Wood, N., Kleinermans, D., Nichols, D. British journal of clinical pharmacology. (2003) [Pubmed]
  34. Effect of posaconazole on cytochrome P450 enzymes: a randomized, open-label, two-way crossover study. Wexler, D., Courtney, R., Richards, W., Banfield, C., Lim, J., Laughlin, M. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. (2004) [Pubmed]
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  37. Synthesis and CYP26A1 inhibitory activity of 1-[benzofuran-2-yl-(4-alkyl/aryl-phenyl)-methyl]-1H-triazoles. Pautus, S., Yee, S.W., Jayne, M., Coogan, M.P., Simons, C. Bioorg. Med. Chem. (2006) [Pubmed]
  38. Increased nitric oxide-dependent nitrosylation of 4,5-diaminofluorescein by oxidants: implications for the measurement of intracellular nitric oxide. Jourd'heuil, D. Free Radic. Biol. Med. (2002) [Pubmed]
  39. Pharmacodynamics of a new triazole, posaconazole, in a murine model of disseminated candidiasis. Andes, D., Marchillo, K., Conklin, R., Krishna, G., Ezzet, F., Cacciapuoti, A., Loebenberg, D. Antimicrob. Agents Chemother. (2004) [Pubmed]
  40. Comparison of voriconazole (UK-109,496) and itraconazole in prevention and treatment of Aspergillus fumigatus endocarditis in guinea pigs. Martin, M.V., Yates, J., Hitchcock, C.A. Antimicrob. Agents Chemother. (1997) [Pubmed]
  41. Multiple-dose pharmacokinetics and safety of the new antifungal triazole BAL4815 after intravenous infusion and oral administration of its prodrug, BAL8557, in healthy volunteers. Schmitt-Hoffmann, A., Roos, B., Maares, J., Heep, M., Spickerman, J., Weidekamm, E., Brown, T., Roehrle, M. Antimicrob. Agents Chemother. (2006) [Pubmed]
  42. Conformations of nucleoside analogue 1-(2'-deoxy-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide in different DNA sequence contexts. Klewer, D.A., Zhang, P., Bergstrom, D.E., Davisson, V.J., LiWang, A.C. Biochemistry (2001) [Pubmed]
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