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Chemical Compound Review

Sportake     N-propyl-N-[2-(2,4,6- trichlorophenoxy)ethy...

Synonyms: Ascurit, Dibavit, Prelude, Sporgon, Sportak, ...
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Disease relevance of Prelude

  • 9. Sprint training improved muscle ion regulation, associated with increased intense exercise performance, at the expense of a greater systemic acidosis [1].
  • In one study (SPRINT I) [Israeli Sprint Study Group 1988], where a regimen of nifedipine 30 mg/day was only started 7 to 21 days after infarction, the exceptionally low mortality rate (5.7%) over 10 months in the placebo group precluded the demonstration of a beneficial effect of nifedipine [2].
  • Body weights were unaffected whereas liver weights were increased in prochloraz-treated animals [3].
  • Furthermore, a good correlation was obtained between the effects of prochloraz on the microsomal formation of benzo[a]pyrene metabolites and on the mutagenic activity of benzo[a]pyrene in the Salmonella typhimurium test [4].
  • A semi-natural field study was carried out to assess the likelihood of a potentiation of toxicity between the ergosterol biosynthesis inhibiting (EBI) fungicide, prochloraz, and the organophosphorus (OP) insecticide, malathion, in the red-legged partridge (Alectoris rufa) [5].

High impact information on Prelude

  • Late gestational exposure to the fungicide prochloraz delays the onset of parturition and causes reproductive malformations in male but not female rat offspring [6].
  • Sexual crosses were used to determine the genetic basis of resistance to the sterol 14 alpha-demethylase inhibitor fungicide prochloraz in the cereal eyespot pathogen Tapesia yallundae [7].
  • Overall, these results together indicate that prochloraz acts directly on the fetal testis to inhibit steroidogenesis and that this effect is exhibited at protein, and not at genomic, level [8].
  • Prochloraz caused mild dysgenesis of the male external genitalia as well as reduced anogenital distance and retention of nipples in male pups [8].
  • Results showed that prochloraz and the mixture significantly reduced plasma and testicular testosterone levels in GD 21 male fetuses, whereas testicular progesterone was increased [9].

Biological context of Prelude


Anatomical context of Prelude

  • The effects on seminal vesicles, LH, T(4), and TSH were also evident in intact prochloraz-exposed young adult rats [3].
  • Chemical analysis of the rat breast milk showed that prochloraz was transferred to the milk [9].
  • In the Hershberger assay, prochloraz exposure at all dose levels (50, 100, and 200 mg/kg) given orally to castrated testosterone (T)-treated males markedly reduced weights of ventral prostate, seminal vesicles, musc. levator ani/bulbocavernosus, and bulbourethral gland [3].
  • There was no significant difference in bond strength values between traditional phosphoric acid/enamel bonding resin and Mirage Bond Dentin and Enamel Adhesive, Clearfil Liner Bond System, and Scotchbond Multi-Purpose Dental Adhesive System [15].
  • The inhibition by prochloraz and NP2EO of the md r1-like mechanism in trout hepatocytes suggests that water pollutants can interfere with P-gp-function in fish and thus may impair the organismal defense against xenobiotics [16].

Associations of Prelude with other chemical compounds

  • The commonly used imidazole fungicide prochloraz was tested for antiandrogenic effects in vitro and in vivo [3].
  • A pronounced decrease of ornithin decarboxylase and PBP C3 mRNA levels was observed for both prochloraz and flutamide [3].
  • Starlings (Stumus vulgaris), however, appeared not to be induced by 180 or 300 mg/kg prochloraz, and no difference in BuChE activity following dosing with malathion was apparent in comparison with controls [17].
  • METHODS: The following adhesives were used: Prime and Bond 2.1 (Dentsply); Single Bond (3M); PrimaBond 97' (BJM); Syntac Sprint (Vivadent); Optibond Solo (Kerr) and Syntac Single Component (Vivadent) [18].
  • Especially the combination with insecticides such as esfenvalerate, where the concentration needed to immobilize 50% of the daphnia was reduced from >3microgL(-1) to less than 0.5microgL(-1) when prochloraz was added, could be problematic as these concentrations are environmentally realistic [19].

Gene context of Prelude

  • Furthermore, fenarimol and prochloraz were potent aromatase inhibitors while endosulfan was a weak inhibitor [20].
  • Upon exposure with E2 or prochloraz a down regulation of ERalpha and ERbeta mRNAs was observed after 48 h of treatment [21].
  • Western blot analyses elicited a decreased ER protein level after 3 h of exposure with prochloraz but after 24 h the ERalpha protein level had recovered to basal level [21].
  • In addition cytochrome P450 (CYP)1A activities in livers were induced by prochloraz, possibly as a result of Ah receptor activation [9].
  • OBJECTIVES: (1) Test the sealing capacity and tensile strength of various adhesive systems: Scotch Bond 1 (Single Bond in USA)(SB1)+Z100, Syntac Sprint (SYN)+Tetric Ceram, Prime and Bond 2.1 (PB21)+TPH Spectrum, F2000 (Adhesive+Compomer) (F2000) and Optibond Solo (OPT)+Prodigy, to perfused teeth (30 cm distilled H2O), in select areas [22].

Analytical, diagnostic and therapeutic context of Prelude

  • Simplified determination of combined residues of prochloraz and its metabolites in vegetable, fruit and wheat samples by gas chromatography [23].
  • LV parameters were calculated using pre-installed software (Mirage Myocardial Perfusion SPECT) (study 1) and the other software (QGS; Cedars-Sinai) (study 2) [24].
  • Strain C964, identified as Aureobacterium sp., effectively reduced the fungitoxic activity of prochloraz in a bioassay and degradation was confirmed by HPLC [25].
  • This later adaptation was also evident in Subject 1 when using his Sprint Flex prosthesis [26].
  • The concentration of copper that causes a reduction of 90% in the residual of day 3 growth of the primary cell culture system was found to be approximately 10 fold more than that of prochloraz [27].


  1. Sprint training enhances ionic regulation during intense exercise in men. McKenna, M.J., Heigenhauser, G.J., McKelvie, R.S., MacDougall, J.D., Jones, N.L. J. Physiol. (Lond.) (1997) [Pubmed]
  2. Myocardial infarction. Secondary prevention with nifedipine. Rafflenbeul, W., Ebner, F. Drugs (1991) [Pubmed]
  3. Antiandrogenic effects in vitro and in vivo of the fungicide prochloraz. Vinggaard, A.M., Nellemann, C., Dalgaard, M., Jørgensen, E.B., Andersen, H.R. Toxicol. Sci. (2002) [Pubmed]
  4. Prochloraz as potent inhibitor of benzo[a]pyrene metabolism and mutagenic activity in rat liver fractions. Antignac, E., Koch, B., Grolier, P., Cassand, P., Narbonne, J.F. Toxicol. Lett. (1990) [Pubmed]
  5. Effects of prochloraz and malathion on the red-legged partridge: a semi-natural field study. Johnston, G., Dawson, A., Walker, C.H. Environ. Pollut. (1996) [Pubmed]
  6. Late gestational exposure to the fungicide prochloraz delays the onset of parturition and causes reproductive malformations in male but not female rat offspring. Noriega, N.C., Ostby, J., Lambright, C., Wilson, V.S., Gray, L.E. Biol. Reprod. (2005) [Pubmed]
  7. Genetic control of resistance to the sterol 14alpha-demethylase inhibitor fungicide prochloraz in the cereal eyespot pathogen Tapesia yallundae. Dyer, P.S., Hansen, J., Delaney, n.u.l.l., Lucas, J.A. Appl. Environ. Microbiol. (2000) [Pubmed]
  8. Mechanisms of action underlying the antiandrogenic effects of the fungicide prochloraz. Laier, P., Metzdorff, S.B., Borch, J., Hagen, M.L., Hass, U., Christiansen, S., Axelstad, M., Kledal, T., Dalgaard, M., McKinnell, C., Brokken, L.J., Vinggaard, A.M. Toxicol. Appl. Pharmacol. (2006) [Pubmed]
  9. Perinatal exposure to the fungicide prochloraz feminizes the male rat offspring. Vinggaard, A.M., Christiansen, S., Laier, P., Poulsen, M.E., Breinholt, V., Jarfelt, K., Jacobsen, H., Dalgaard, M., Nellemann, C., Hass, U. Toxicol. Sci. (2005) [Pubmed]
  10. Discovering metabolites of post-harvest fungicides in citrus with liquid chromatography/time-of-flight mass spectrometry and ion trap tandem mass spectrometry. Thurman, E.M., Ferrer, I., Zweigenbaum, J.A., García-Reyes, J.F., Woodman, M., Fernández-Alba, A.R. Journal of chromatography. A. (2005) [Pubmed]
  11. Impact of environmental chemicals on the thyroid hormone function in pituitary rat GH3 cells. Ghisari, M., Bonefeld-Jorgensen, E.C. Mol. Cell. Endocrinol. (2005) [Pubmed]
  12. In vitro effects of an imidazole antifungal, prochloraz, on spectral and catalytic properties of microsomal cytochromes P-450. Antignac, E., Koch, B., Delaforge, M., Narbonne, J.F. Xenobiotica (1991) [Pubmed]
  13. The profile of rat liver enzyme induction produced by prochloraz and its major metabolites. Needham, D., Creedy, C.L., Dawson, J.R. Xenobiotica (1992) [Pubmed]
  14. In vivo and in vitro effects of prochloraz and nonylphenol ethoxylates on trout spermatogenesis. Le Gac, F., Thomas, J.L., Mourot, B., Loir, M. Aquat. Toxicol. (2001) [Pubmed]
  15. An in vitro shear bond strength study of enamel/dentin bonding systems on enamel. Reifeis, P.E., Cochran, M.A., Moore, B.K. Operative dentistry. (1995) [Pubmed]
  16. Prochloraz and nonylphenol diethoxylate inhibit an mdr1-like activity in vitro, but do not alter hepatic levels of P-glycoprotein in trout exposed in vivo. Sturm, A., Cravedi, J.P., Segner, H. Aquat. Toxicol. (2001) [Pubmed]
  17. The study of interactive effects of pollutants: a biomarker approach. Johnston, G. Sci. Total Environ. (1995) [Pubmed]
  18. Evaporation of solvent in one-bottle adhesives. Abate, P.F., Rodriguez, V.I., Macchi, R.L. Journal of dentistry. (2000) [Pubmed]
  19. Is prochloraz a potent synergist across aquatic species? A study on bacteria, daphnia, algae and higher plants. Cedergreen, N., Kamper, A., Streibig, J.C. Aquat. Toxicol. (2006) [Pubmed]
  20. Effects of currently used pesticides in assays for estrogenicity, androgenicity, and aromatase activity in vitro. Andersen, H.R., Vinggaard, A.M., Rasmussen, T.H., Gjermandsen, I.M., Bonefeld-Jørgensen, E.C. Toxicol. Appl. Pharmacol. (2002) [Pubmed]
  21. Effects of the pesticides prochloraz and methiocarb on human estrogen receptor alpha and beta mRNA levels analyzed by on-line RT-PCR. Hofmeister, M.V., Bonefeld-Jørgensen, E.C. Toxicology in vitro : an international journal published in association with BIBRA. (2004) [Pubmed]
  22. Sealing and dentin bond strength of adhesive systems in selected areas of perfused teeth. Escribano, N., Del-Nero, O., de la Macorra, J.C. Dental materials : official publication of the Academy of Dental Materials. (2001) [Pubmed]
  23. Simplified determination of combined residues of prochloraz and its metabolites in vegetable, fruit and wheat samples by gas chromatography. De Paoli, M., Taccheo Barbina, M., Damiano, V., Fabbro, D., Bruno, R. Journal of chromatography. A. (1997) [Pubmed]
  24. Validation of left ventricular function from gated single photon computed emission tomography by using a scintillator-photodiode camera: a dynamic myocardial phantom study. Kubo, N., Mabuchi, M., Katoh, C., Arai, H., Morita, K., Tsukamoto, E., Morita, Y., Tamaki, N. Nuclear medicine communications. (2002) [Pubmed]
  25. Degradation of prochloraz and 2,4,6-trichlorophenol by environmental bacterial strains. Bock, C., Kroppenstedt, R.M., Schmidt, U., Diekmann, H. Appl. Microbiol. Biotechnol. (1996) [Pubmed]
  26. Biomechanical adaptations of transtibial amputee sprinting in athletes using dedicated prostheses. Buckley, J.G. Clinical biomechanics (Bristol, Avon) (2000) [Pubmed]
  27. The further development of rainbow trout primary epithelial cell cultures as a diagnostic tool in ecotoxicology risk assessment. Dowling, K., Mothersill, C. Aquat. Toxicol. (2001) [Pubmed]
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