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Chemical Compound Review

Ornalin     3-(3,5-dichlorophenyl)-5- ethenyl-5-methyl...

Synonyms: Ranilan, Ronilan, Vorlan, VINCLOZOLIN, Vinclozoline, ...
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Disease relevance of Ornalin

  • Pregnant rabbits were dosed orally with vinclozolin (10 mg/kg body weight) or carrot paste vehicle once daily for 6 wk beginning at midgestation and continuing through nursing until Postpartum Week 4 [1].
  • Environmental hormone disruptors: evidence that vinclozolin developmental toxicity is mediated by antiandrogenic metabolites [2].
  • Dosing the animals with a combination of a 1:1 mixture of vinclozolin and procymidone resulted in a weight reduction in the reproductive organs and an increase of serum LH and FSH as early as with 10 mg/kg combined dose [3].
  • Perinatal administration of 100 or 200 mg vinclozolin (V) kg-1 day-1 during sexual differentiation in rats induces female-like anogenital distance (AGD), retained nipples, cleft phallus with hypospadias, suprainguinal ectopic scrota/testes, a vaginal pouch, epididymal granulomas, and small to absent sex accessory glands in male offspring [4].
  • We therefore investigated the effect of 1- and 24-h treatments with vinclozolin at concentrations of 25, 50, 100 microg/ml and iprodione at concentration of 62.5, 125, 250 microg/ml on malonaldehyde and free radical production and on reduced glutathione levels in the human HepG2 hepatoma cell line [5].

High impact information on Ornalin

  • Antiandrogenic environmental disrupting chemicals, such as 1,1-dichloro-2,2-bis(p-chlorophenyl)ethylene, vinclozolin, or nitrofen, also disrupted the intranuclear fluorescence foci [6].
  • The mechanism of antiandrogenic activity of vinclozolin (3-(3,5-dichlorophenyl)-5-methyl-5-vinyloxazolidine-2,4-dione), a dicarboximide fungicide under investigation for its potential adverse effects on human male reproduction, was investigated using recombinant human androgen receptor (AR) [7].
  • Vinclozolin and two of its metabolites, designated M1 and M2, have been shown to bind and inhibit the function of the rat and human androgen receptor [8].
  • The expression pattern of several of the genes during embryonic development were found to be altered in the vinclozolin F(1) and F2 generation testis [9].
  • Analysis of the transgenerational epigenetic effects on the male germline (i.e. sperm) identified 25 candidate DNA sequences with altered methylation patterns in the vinclozolin generation sperm [9].

Chemical compound and disease context of Ornalin


Biological context of Ornalin


Anatomical context of Ornalin


Associations of Ornalin with other chemical compounds


Gene context of Ornalin

  • Vinclozolin does not alter progesterone receptor (PR) function in vivo despite inhibition of PR binding by its metabolites in vitro [21].
  • The result suggested that induction of CYP1A1 by vinclozolin account for its enhancing effect on genotoxicity caused by BaP [22].
  • In general, however, Vinclozolin has a complex pattern of induction and suppression of CYP-dependent enzymes, as shown from the reduced expression of various monooxygenases depending upon dose, sex or organ considered [23].
  • Several environmental chemicals, including metabolites of the fungicide vinclozolin and the pesticide DDT, disrupt male reproductive development and function by inhibiting androgen receptor mediated events [24].
  • We found no in vivo effect of vinclozolin on androgen receptor expression [25].

Analytical, diagnostic and therapeutic context of Ornalin


  1. Sex differences and the development of the rabbit brain: effects of vinclozolin. Bisenius, E.S., Veeramachaneni, D.N., Sammonds, G.E., Tobet, S. Biol. Reprod. (2006) [Pubmed]
  2. Environmental hormone disruptors: evidence that vinclozolin developmental toxicity is mediated by antiandrogenic metabolites. Kelce, W.R., Monosson, E., Gamcsik, M.P., Laws, S.C., Gray, L.E. Toxicol. Appl. Pharmacol. (1994) [Pubmed]
  3. The combined effects of vinclozolin and procymidone do not deviate from expected additivity in vitro and in vivo. Nellemann, C., Dalgaard, M., Lam, H.R., Vinggaard, A.M. Toxicol. Sci. (2003) [Pubmed]
  4. Environmental antiandrogens: low doses of the fungicide vinclozolin alter sexual differentiation of the male rat. Gray, L.E., Ostby, J., Monosson, E., Kelce, W.R. Toxicology and industrial health. (1999) [Pubmed]
  5. Adaptation to oxidative stress: effects of vinclozolin and iprodione on the HepG2 cell line. Radice, S., Marabini, L., Gervasoni, M., Ferraris, M., Chiesara, E. Toxicology (1998) [Pubmed]
  6. The subnuclear three-dimensional image analysis of androgen receptor fused to green fluorescence protein. Tomura, A., Goto, K., Morinaga, H., Nomura, M., Okabe, T., Yanase, T., Takayanagi, R., Nawata, H. J. Biol. Chem. (2001) [Pubmed]
  7. Androgen receptor antagonist versus agonist activities of the fungicide vinclozolin relative to hydroxyflutamide. Wong, C., Kelce, W.R., Sar, M., Wilson, E.M. J. Biol. Chem. (1995) [Pubmed]
  8. Mode of action: inhibition of androgen receptor function--vinclozolin-induced malformations in reproductive development. Kavlock, R., Cummings, A. Crit. Rev. Toxicol. (2005) [Pubmed]
  9. Transgenerational Epigenetic Imprinting of the Male Germline by Endocrine Disruptor Exposure during Gonadal Sex Determination. Chang, H.S., Anway, M.D., Rekow, S.S., Skinner, M.K. Endocrinology (2006) [Pubmed]
  10. Repeated 28-day oral toxicity study of vinclozolin in rats based on the draft protocol for the "Enhanced OECD Test Guideline No. 407" to detect endocrine effects. Shin, J.H., Moon, H.J., Kim, T.S., Kang, I.H., Ki, H.Y., Choi, K.S., Han, S.Y. Arch. Toxicol. (2006) [Pubmed]
  11. Interlaboratory comparison of four in vitro assays for assessing androgenic and antiandrogenic activity of environmental chemicals. Körner, W., Vinggaard, A.M., Térouanne, B., Ma, R., Wieloch, C., Schlumpf, M., Sultan, C., Soto, A.M. Environ. Health Perspect. (2004) [Pubmed]
  12. Androgens and environmental antiandrogens affect reproductive development and play behavior in the Sprague-Dawley rat. Hotchkiss, A.K., Ostby, J.S., Vandenburgh, J.G., Gray, L.E. Environ. Health Perspect. (2002) [Pubmed]
  13. UV filters with antagonistic action at androgen receptors in the MDA-kb2 cell transcriptional-activation assay. Ma, R., Cotton, B., Lichtensteiger, W., Schlumpf, M. Toxicol. Sci. (2003) [Pubmed]
  14. Characterization of the period of sensitivity of fetal male sexual development to vinclozolin. Wolf, C.J., LeBlanc, G.A., Ostby, J.S., Gray, L.E. Toxicol. Sci. (2000) [Pubmed]
  15. The weanling male rat as an assay for endocrine disruption: preliminary observations. Ashby, J., Lefevre, P.A. Regulatory toxicology and pharmacology : RTP. (1997) [Pubmed]
  16. Effect of the anti-androgenic endocrine disruptor vinclozolin on embryonic testis cord formation and postnatal testis development and function. Uzumcu, M., Suzuki, H., Skinner, M.K. Reprod. Toxicol. (2004) [Pubmed]
  17. Separation of fungicides by micellar electrokinetic capillary chromatography. Penmetsa, K.V., Leidy, R.B., Shea, D. Electrophoresis (1997) [Pubmed]
  18. Peripubertal exposure to the antiandrogenic fungicide, vinclozolin, delays puberty, inhibits the development of androgen-dependent tissues, and alters androgen receptor function in the male rat. Monosson, E., Kelce, W.R., Lambright, C., Ostby, J., Gray, L.E. Toxicology and industrial health. (1999) [Pubmed]
  19. Simultaneous determination of vinclozolin and detection of its degradation products in mouse plasma, serum and urine, and from rabbit bile, by high-performance liquid chromatography. Dhananjeyan, M.R., Erhardt, P.W., Corbitt, C. Journal of chromatography. A. (2006) [Pubmed]
  20. Effects of environmental antiandrogens on reproductive development in experimental animals. Gray, L.E., Ostby, J., Furr, J., Wolf, C.J., Lambright, C., Parks, L., Veeramachaneni, D.N., Wilson, V., Price, M., Hotchkiss, A., Orlando, E., Guillette, L. Hum. Reprod. Update (2001) [Pubmed]
  21. Vinclozolin does not alter progesterone receptor (PR) function in vivo despite inhibition of PR binding by its metabolites in vitro. Laws, S.C., Carey, S.A., Kelce, W.R., Cooper, R.L., Gray, L.E. Toxicology (1996) [Pubmed]
  22. Vinclozolin, a widely used fungizide, enhanced BaP-induced micronucleus formation in human derived hepatoma cells by increasing CYP1A1 expression. Wu, X.J., Lu, W.Q., Roos, P.H., Mersch-Sundermann, V. Toxicol. Lett. (2005) [Pubmed]
  23. The genetic and non-genetic toxicity of the fungicide Vinclozolin. Hrelia, P., Fimognari, C., Maffei, F., Vigagni, F., Mesirca, R., Pozzetti, L., Paolini, M., Cantelli Forti, G. Mutagenesis (1996) [Pubmed]
  24. Antiandrogens as environmental endocrine disruptors. Kelce, W.R., Gray, L.E., Wilson, E.M. Reprod. Fertil. Dev. (1998) [Pubmed]
  25. Embryonic exposure to the fungicide vinclozolin causes virilization of females and alteration of progesterone receptor expression in vivo: an experimental study in mice. Buckley, J., Willingham, E., Agras, K., Baskin, L.S. Environmental health : a global access science source [electronic resource]. (2006) [Pubmed]
  26. OECD validation of the Hershberger assay in Japan: phase 2 dose response of methyltestosterone, vinclozolin, and p,p'-DDE. Yamasaki, K., Sawaki, M., Ohta, R., Okuda, H., Katayama, S., Yamada, T., Ohta, T., Kosaka, T., Owens, W. Environ. Health Perspect. (2003) [Pubmed]
  27. Determination of the fungicide vinclozolin in honey and bee larvae by solid-phase and solvent extraction with gas chromatography and electron-capture and mass spectrometric detection. Bernal, J.L., del Nozal, M.J., Rivera, J.M., Jiménez, J.J., Atienza, J. Journal of chromatography. A. (1996) [Pubmed]
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