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Chemical Compound Review

Pfizer     (2R,3R)-2-(2,4- difluorophenyl)-3-(5...

Synonyms: Vfend, Voriconazol, Voriconazole, Voriconazolum, CHEMBL638, ...
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Disease relevance of Voriconazole


Psychiatry related information on Voriconazole

  • After discontinuing voriconazole the hallucinations decreased in intensity by the 2nd day and ceased altogether by the 3rd day [6].
  • From a medical perspective, confirmation of the diagnosis, the need for long-term antifungal therapy, the need for long-term patient compliance, and the use of the new antifungal agent voriconazole are emphasized [7].
  • In multivariable models, salvage therapy with the combination of voriconazole and caspofungin was associated with reduced mortality, compared with therapy with voriconazole (HR, 0.28; 95% CI, 0.28-0.92; P=.011), independent of other prognostic variables (e.g., receipt of transplant and type of conditioning therapy) [8].

High impact information on Voriconazole


Chemical compound and disease context of Voriconazole


Biological context of Voriconazole

  • METHODS: In a controlled, open-label study, single oral doses of 400 mg voriconazole were administered to 16 healthy men stratified for CYP2C19 genotype before and on day 1 and day 15 of concomitant SJW intake (300 mg LI 160 3 times daily) [17].
  • CONCLUSIONS: In this population of severely immunocompromised patients with life-threatening IFI who have failed or were intolerant to standard antifungal therapy, voriconazole demonstrated substantial efficacy and an acceptable level of toxicity [18].
  • Voriconazole has several important safety issues, including visual adverse events, hepatic enzyme elevation and skin reactions, as well as a number of drug interactions [19].
  • The voriconazole free drug AUC/MIC ratios were similar for all of the organisms studied (range, 11 to 58; mean +/- standard deviation, 24 +/- 17 [P = 0.45]) [20].
  • Voriconazole is rapidly absorbed within 2 hours after oral administration and the oral bioavailability is over 90%, thus allowing switching between oral and intravenous formulations when clinically appropriate [21].

Anatomical context of Voriconazole


Associations of Voriconazole with other chemical compounds


Gene context of Voriconazole

  • Activity against C. krusei in the presence of voriconazole was greatest when MDM were activated with IFN-gamma rather than GM-CSF [31].
  • Five hematopoietic stem cell transplant recipients that developed breakthrough Candida glabrata bloodstream infections while receiving voriconazole are described and the clinical management and susceptibility profiles of their isolates are reported [32].
  • These results were confirmed by expressing the CYP51 genes from C. krusei and C. albicans in Saccharomyces cerevisiae and determining the susceptibility of the transformants to voriconazole and fluconazole [33].
  • Using different inoculation models of IA, we found that Toll-deficient Drosophila flies exposed to voriconazole (VRC), the preferred drug for the treatment of IA in humans, had significantly better survival rates and lower tissue fungal burdens than did those not exposed to VRC [34].
  • Our primary objective was to compare the results of voriconazole disk diffusion testing of Candida spp. performed by centers participating in the ARTEMIS program with disk diffusion and MIC results obtained by the central reference laboratory [35].

Analytical, diagnostic and therapeutic context of Voriconazole


  1. Improved outcome in central nervous system aspergillosis, using voriconazole treatment. Schwartz, S., Ruhnke, M., Ribaud, P., Corey, L., Driscoll, T., Cornely, O.A., Schuler, U., Lutsar, I., Troke, P., Thiel, E. Blood (2005) [Pubmed]
  2. Pseudallescheria boydii (Anamorph Scedosporium apiospermum). Infection in solid organ transplant recipients in a tertiary medical center and review of the literature. Castiglioni, B., Sutton, D.A., Rinaldi, M.G., Fung, J., Kusne, S. Medicine (Baltimore) (2002) [Pubmed]
  3. Successful treatment with voriconazole of invasive aspergillosis in chronic granulomatous disease. van 't Hek, L.G., Verweij, P.E., Weemaes, C.M., van Dalen, R., Yntema, J.B., Meis, J.F. Am. J. Respir. Crit. Care Med. (1998) [Pubmed]
  4. Effect of voriconazole on the pharmacokinetics of cyclosporine in renal transplant patients. Romero, A.J., Pogamp, P.L., Nilsson, L.G., Wood, N. Clin. Pharmacol. Ther. (2002) [Pubmed]
  5. Topical voriconazole as a novel treatment for fungal keratitis. Sponsel, W., Chen, N., Dang, D., Paris, G., Graybill, J., Najvar, L.K., Zhou, L., Lam, K.W., Glickman, R., Scribbick, F. Antimicrob. Agents Chemother. (2006) [Pubmed]
  6. Voriconazole-induced musical hallucinations. Agrawal, A.K., Sherman, L.K. Infection (2004) [Pubmed]
  7. Treatment of a chronic Scedosporium apiospermum vertebral osteomyelitis. Case report. German, J.W., Kellie, S.M., Pai, M.P., Turner, P.T. Neurosurgical focus [electronic resource]. (2004) [Pubmed]
  8. Combination antifungal therapy for invasive aspergillosis. Marr, K.A., Boeckh, M., Carter, R.A., Kim, H.W., Corey, L. Clin. Infect. Dis. (2004) [Pubmed]
  9. Potent cytochrome P450 2C19 genotype-related interaction between voriconazole and the cytochrome P450 3A4 inhibitor ritonavir. Mikus, G., Schöwel, V., Drzewinska, M., Rengelshausen, J., Ding, R., Riedel, K.D., Burhenne, J., Weiss, J., Thomsen, T., Haefeli, W.E. Clin. Pharmacol. Ther. (2006) [Pubmed]
  10. Voriconazole, but not terbinafine, markedly reduces alfentanil clearance and prolongs its half-life. Saari, T.I., Laine, K., Leino, K., Valtonen, M., Neuvonen, P.J., Olkkola, K.T. Clin. Pharmacol. Ther. (2006) [Pubmed]
  11. Effect of voriconazole on the pharmacokinetics and pharmacodynamics of intravenous and oral midazolam. Saari, T.I., Laine, K., Leino, K., Valtonen, M., Neuvonen, P.J., Olkkola, K.T. Clin. Pharmacol. Ther. (2006) [Pubmed]
  12. Current approaches to diagnosis and treatment of invasive aspergillosis. Segal, B.H., Walsh, T.J. Am. J. Respir. Crit. Care Med. (2006) [Pubmed]
  13. Invasive oesophageal candidiasis: current and developing treatment options. Vazquez, J.A. Drugs (2003) [Pubmed]
  14. 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]
  15. Sequential or combination antifungal therapy with voriconazole and liposomal amphotericin B in a Guinea pig model of invasive aspergillosis. Kirkpatrick, W.R., Coco, B.J., Patterson, T.F. Antimicrob. Agents Chemother. (2006) [Pubmed]
  16. Synergism of voriconazole and terbinafine against Candida albicans isolates from human immunodeficiency virus-infected patients with oropharyngeal candidiasis. Weig, M., Müller, F.M. Antimicrob. Agents Chemother. (2001) [Pubmed]
  17. Opposite effects of short-term and long-term St John's wort intake on voriconazole pharmacokinetics. Rengelshausen, J., Banfield, M., Riedel, K.D., Burhenne, J., Weiss, J., Thomsen, T., Walter-Sack, I., Haefeli, W.E., Mikus, G. Clin. Pharmacol. Ther. (2005) [Pubmed]
  18. Salvage therapy with voriconazole for invasive fungal infections in patients failing or intolerant to standard antifungal therapy. Baden, L.R., Katz, J.T., Fishman, J.A., Koziol, C., DelVecchio, A., Doran, M., Rubin, R.H. Transplantation (2003) [Pubmed]
  19. Newer systemic antifungal agents : pharmacokinetics, safety and efficacy. Boucher, H.W., Groll, A.H., Chiou, C.C., Walsh, T.J. Drugs (2004) [Pubmed]
  20. 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]
  21. Pharmacokinetic/pharmacodynamic profile of voriconazole. Theuretzbacher, U., Ihle, F., Derendorf, H. Clinical pharmacokinetics. (2006) [Pubmed]
  22. Voriconazole Concentration in Human Aqueous Humor and Plasma during Topical or Combined Topical and Systemic Administration for Fungal Keratitis. Thiel, M.A., Zinkernagel, A.S., Burhenne, J., Kaufmann, C., Haefeli, W.E. Antimicrob. Agents Chemother. (2007) [Pubmed]
  23. 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]
  24. Voriconazole inhibition of the metabolism of tacrolimus in a liver transplant recipient and in human liver microsomes. Venkataramanan, R., Zang, S., Gayowski, T., Singh, N. Antimicrob. Agents Chemother. (2002) [Pubmed]
  25. Voriconazole inhibits fungal growth without impairing antigen presentation or T-cell activation. Van Epps, H.L., Feldmesser, M., Pamer, E.G. Antimicrob. Agents Chemother. (2003) [Pubmed]
  26. Effects of the antifungals voriconazole and fluconazole on the pharmacokinetics of s-(+)- and R-(-)-Ibuprofen. Hynninen, V.V., Olkkola, K.T., Leino, K., Lundgren, S., Neuvonen, P.J., Rane, A., Valtonen, M., Vyyryläinen, H., Laine, K. Antimicrob. Agents Chemother. (2006) [Pubmed]
  27. Antifungal susceptibilities of clinical isolates of Candida species, Cryptococcus neoformans, and Aspergillus species from Taiwan: surveillance of multicenter antimicrobial resistance in Taiwan program data from 2003. Hsueh, P.R., Lau, Y.J., Chuang, Y.C., Wan, J.H., Huang, W.K., Shyr, J.M., Yan, J.J., Yu, K.W., Wu, J.J., Ko, W.C., Yang, Y.C., Liu, Y.C., Teng, L.J., Liu, C.Y., Luh, K.T. Antimicrob. Agents Chemother. (2005) [Pubmed]
  28. Studies of in vitro activities of voriconazole and itraconazole against Aspergillus hyphae using viability staining. Lass-Flörl, C., Nagl, M., Speth, C., Ulmer, H., Dierich, M.P., Würzner, R. Antimicrob. Agents Chemother. (2001) [Pubmed]
  29. Posaconazole Enhances the Activity of Amphotericin B against Aspergillus Hyphae In Vitro. Perkhofer, S., Lugger, H., Dierich, M.P., Lass-Flörl, C. Antimicrob. Agents Chemother. (2007) [Pubmed]
  30. Increased virulence of Zygomycetes organisms following exposure to voriconazole: a study involving fly and murine models of zygomycosis. Lamaris, G.A., Ben-Ami, R., Lewis, R.E., Chamilos, G., Samonis, G., Kontoyiannis, D.P. J. Infect. Dis. (2009) [Pubmed]
  31. Effects of voriconazole, granulocyte-macrophage colony-stimulating factor, and interferon gamma on intracellular fluconazole-resistant Candida glabrata and Candida krusei in human monocyte-derived macrophages. Baltch, A.L., Bopp, L.H., Smith, R.P., Ritz, W.J., Carlyn, C.J., Michelsen, P.B. Diagn. Microbiol. Infect. Dis. (2005) [Pubmed]
  32. Candida glabrata fungemia in transplant patients receiving voriconazole after fluconazole. Alexander, B.D., Schell, W.A., Miller, J.L., Long, G.D., Perfect, J.R. Transplantation (2005) [Pubmed]
  33. Genetic basis for differential activities of fluconazole and voriconazole against Candida krusei. Fukuoka, T., Johnston, D.A., Winslow, C.A., de Groot, M.J., Burt, C., Hitchcock, C.A., Filler, S.G. Antimicrob. Agents Chemother. (2003) [Pubmed]
  34. Toll-deficient Drosophila flies as a fast, high-throughput model for the study of antifungal drug efficacy against invasive aspergillosis and Aspergillus virulence. Lionakis, M.S., Lewis, R.E., May, G.S., Wiederhold, N.P., Albert, N.D., Halder, G., Kontoyiannis, D.P. J. Infect. Dis. (2005) [Pubmed]
  35. Comparison of results of voriconazole disk diffusion testing for Candida species with results from a central reference laboratory in the ARTEMIS global antifungal surveillance program. Pfaller, M.A., Boyken, L., Messer, S.A., Tendolkar, S., Hollis, R.J., Diekema, D.J. J. Clin. Microbiol. (2005) [Pubmed]
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