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Chemical Compound Review

Fenamine     6-chloro-N'-ethyl-N-propan-2- yl-1,3,5...

Synonyms: Atazinax, Atrasine, Fenatrol, Gesaprim, Gesaprin, ...
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Disease relevance of Fenamine


Psychiatry related information on Fenamine

  • Time-response curves for cAMP induction and concentration-response curves for aromatase induction by vinclozolin, atrazine, and IBMX were similar, suggesting that the mechanism of aromatase induction by these pesticides is mediated through inhibition of phosphodiesterase activity [6].
  • Copulatory plugs form from coagulated ejaculate, and are routinely displaced in this species by the penis of a subsequent mate during copulation (Parga [2003] Int. J. Primatol. 24:889-899) [7].
  • Adverse effects of prenatal exposure to atrazine during a critical period of mammary gland growth [8].

High impact information on Fenamine


Chemical compound and disease context of Fenamine

  • The properties of the quinone acceptor complex in the photosynthetic reaction center of the atrazine-resistant Rhodopseudomonas viridis mutant A2 (Glu L212-->Lys) were studied by EPR spectroscopy and by photoelectric measurements [12].
  • Rhodococcus sp. strain TE1, which possesses the catabolic gene (atrA) for the N-dealkylation of the herbicides atrazine and simazine, was able to dechlorinate the dealkylated metabolites of atrazine and simazine when carrying the trzA gene on a plasmid [13].
  • Multiple linear regression analyses revealed that levels of the herbicides atrazine, metolachlor, and cyanzinc were each significant predictors of community IUGR rates in southern Iowa after controlling for several potentially confounding factors including maternal smoking and socioeconomic variables [14].
  • Here, we describe the frequencies at which these malformations occur and compare them with morphologies induced by the estrogen, 17beta-estradiol (E2) , and the antiandrogen cyproterone acetate, as a first step in testing the hypothesis that the effects of atrazine are a combination of demasculinization and feminization [15].
  • Whereas atrazine and cyanuric acid showed no significant toxic effect on the cells, phenol reduces growth and activates or induces typical membrane-adaptive responses known for the genus Pseudomonas [16].

Biological context of Fenamine


Anatomical context of Fenamine

  • After isolation and renaturation, the ability of the recombinant D1 protein to bind atrazine and pigments from barley thylakoids was demonstrated [21].
  • Gonadal malformations induced by atrazine include hermaphrodites and males with multiple testes [single sex polygonadism (SSP)], and effects occur at concentrations as low as 0.1 ppb (microg/L) [15].
  • At both levels tested, atrazine caused chromosomal damage to the CHO cells [22].
  • No peroxisome proliferation was observed in the liver or kidneys of mice treated with atrazine [23].
  • Male adult African clawed frogs (Xenopus laevis) were exposed to three nominal concentrations of atrazine (1, 25, or 250 microg atrazine/l) for 36 days, and testicular aromatase activity and CYP19 gene expression, as well as concentrations of the plasma sex steroids testosterone (T) and 17beta-estradiol (E2), and gonad size (GSI) were measured [24].

Associations of Fenamine with other chemical compounds

  • Here, we report the structural characterisation of triazine binding by crystallographic refinement of complexes of the RC either with the triazine inhibitor atrazine (Protein Data Bank (PDB) entry 5PRC) or with the chiral atrazine derivatives, DG-420314 (S(-) enantiomer, PDB entry 6PRC) or DG-420315 (R(+) enantiomer, PDB entry 7PRC) [4].
  • Accelerator mass spectrometry (AMS) has been applied to the detection of 14C-labeled urinary metabolites of the triazine herbicide, atrazine, and the analytical performance of AMS has been directly compared to that of liquid scintillation counting (LSC) [25].
  • We have developed an isotope dilution high-performance liquid chromatography/tandem mass spectrometry (HPLC/MS/MS) method for quantifying the urinary metabolites of the pesticides atrazine, malathion, and 2,4-dichlorophenoxyacetic acid (2,4-D) [26].
  • By introducing LiCl into the MIP, atrazine was reduced below -800 mV vs Ag/AgCl reference electrode, at pH 3 [27].
  • In addition to atrazine, simazine, and propazine, two metabolites--atrazine-desethyl and atrazine-desisopropyl--induced aromatase activity in H295R cells concentration-dependently (0.3-30 microM) and with potencies similar to those of the parent triazines [28].

Gene context of Fenamine

  • In this study, the third gene in the atrazine catabolic pathway, atzC, was cloned from a Pseudomonas sp. strain ADP cosmid library as a 25-kb EcoRI DNA fragment in Escherichia coli [29].
  • In this study, we show that this fragment also contained the second gene of the atrazine metabolic pathway, atzB [30].
  • Reverse transcriptase PCR analysis indicated that the psbA1 gene and the psbA2/psbA3 gene(s) were expressed in photosynthetically grown cells in the presence of atrazine [31].
  • The gamma- and delta-isomers of hexachlorocyclohexane, congeners of dichlorodiphenyl-trichloroethane (DDT; p,p'-DDT; p,p'-DDE; o,p'-DDT), dieldrin, atrazine, and pentachlorophenol, caused a statistically significant inhibition of specific binding of [3H]5 alpha-DHT to the androgen receptor that ranged from 100% (p,p'-DDE) to 25% (dieldrin) [32].
  • Selection of an atrazine-resistant tobacco cell line having a mutant psbA gene [33].
  • On the basis of the present data, atrazine should be included among the environmental contaminants potentially able to signal via GPR30 in eliciting estrogenic action [34].

Analytical, diagnostic and therapeutic context of Fenamine

  • Induced new mutation of D1 serine-268 in soybean photosynthetic cell cultures produced atrazine resistance, increased stability of S2QB- and S3QB- states, and increased sensitivity to light stress [35].
  • Atrazine recovery as determined by ELISA averaged 92.8% following MISPE and 79.6% for the unpurified extracts [36].
  • Atrazine recovery as determined by HPLC from beef liver homogenates spiked to levels from 0.005 to 0.5 ppm averaged 88.7% following MISPE and 60.9% for the unpurified extracts [36].
  • The performance of both the colorimetric and CDH biosensor detection was investigated and both methods were applied for determination of the model compound atrazine in spiked surface water samples [37].
  • Analytical performance of accelerator mass spectrometry and liquid scintillation counting for detection of 14C-labeled atrazine metabolites in human urine [25].


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  2. Analysis of the diversity of a sheep antibody repertoire as revealed from a bacteriophage display library. Charlton, K.A., Moyle, S., Porter, A.J., Harris, W.J. J. Immunol. (2000) [Pubmed]
  3. A review of epidemiologic studies of triazine herbicides and cancer. Sathiakumar, N., Delzell, E. Crit. Rev. Toxicol. (1997) [Pubmed]
  4. Refined crystal structures of reaction centres from Rhodopseudomonas viridis in complexes with the herbicide atrazine and two chiral atrazine derivatives also lead to a new model of the bound carotenoid. Lancaster, C.R., Michel, H. J. Mol. Biol. (1999) [Pubmed]
  5. Atrazine chlorohydrolase from Pseudomonas sp. strain ADP is a metalloenzyme. Seffernick, J.L., McTavish, H., Osborne, J.P., de Souza, M.L., Sadowsky, M.J., Wackett, L.P. Biochemistry (2002) [Pubmed]
  6. Induction and inhibition of aromatase (CYP19) activity by various classes of pesticides in H295R human adrenocortical carcinoma cells. Sanderson, J.T., Boerma, J., Lansbergen, G.W., van den Berg, M. Toxicol. Appl. Pharmacol. (2002) [Pubmed]
  7. High-resolution X-ray computed tomography scanning of primate copulatory plugs. Parga, J.A., Maga, M., Overdorff, D.J. Am. J. Phys. Anthropol. (2006) [Pubmed]
  8. Adverse effects of prenatal exposure to atrazine during a critical period of mammary gland growth. Rayner, J.L., Enoch, R.R., Fenton, S.E. Toxicol. Sci. (2005) [Pubmed]
  9. Barbiturase, a novel zinc-containing amidohydrolase involved in oxidative pyrimidine metabolism. Soong, C.L., Ogawa, J., Sakuradani, E., Shimizu, S. J. Biol. Chem. (2002) [Pubmed]
  10. The role of cytochrome c-550 as studied through reverse genetics and mutant characterization in Synechocystis sp. PCC 6803. Shen, J.R., Vermaas, W., Inoue, Y. J. Biol. Chem. (1995) [Pubmed]
  11. A framework for human relevance analysis of information on carcinogenic modes of action. Meek, M.E., Bucher, J.R., Cohen, S.M., Dellarco, V., Hill, R.N., Lehman-McKeeman, L.D., Longfellow, D.G., Pastoor, T., Seed, J., Patton, D.E. Crit. Rev. Toxicol. (2003) [Pubmed]
  12. Structural and functional consequences of a Glu L212-->Lys mutation in the QB binding site of the photosynthetic reaction center of Rhodopseudomonas viridis. Albert, I., Leibl, W., Ewald, G., Michel, H., Rutherford, A.W. Biochemistry (1994) [Pubmed]
  13. Cloning and expression of the s-triazine hydrolase gene (trzA) from Rhodococcus corallinus and development of Rhodococcus recombinant strains capable of dealkylating and dechlorinating the herbicide atrazine. Shao, Z.Q., Seffens, W., Mulbry, W., Behki, R.M. J. Bacteriol. (1995) [Pubmed]
  14. Intrauterine growth retardation in Iowa communities with herbicide-contaminated drinking water supplies. Munger, R., Isacson, P., Hu, S., Burns, T., Hanson, J., Lynch, C.F., Cherryholmes, K., Van Dorpe, P., Hausler, W.J. Environ. Health Perspect. (1997) [Pubmed]
  15. Characterization of atrazine-induced gonadal malformations in African clawed frogs (Xenopus laevis) and comparisons with effects of an androgen antagonist (cyproterone acetate) and exogenous estrogen (17beta-estradiol): Support for the demasculinization/feminization hypothesis. Hayes, T.B., Stuart, A.A., Mendoza, M., Collins, A., Noriega, N., Vonk, A., Johnston, G., Liu, R., Kpodzo, D. Environ. Health Perspect. (2006) [Pubmed]
  16. Simultaneous degradation of atrazine and phenol by Pseudomonas sp. strain ADP: effects of toxicity and adaptation. Neumann, G., Teras, R., Monson, L., Kivisaar, M., Schauer, F., Heipieper, H.J. Appl. Environ. Microbiol. (2004) [Pubmed]
  17. In vitro expression and characterization of the translation start site of the psbA gene product (QB protein) from higher plants. Cohen, B.N., Coleman, T.A., Schmitt, J.J., Weissbach, H. Nucleic Acids Res. (1984) [Pubmed]
  18. A serine-to-threonine substitution in the triazine herbicide-binding protein in potato cells results in atrazine resistance without impairing productivity. Smeda, R.J., Hasegawa, P.M., Goldsbrough, P.B., Singh, N.K., Weller, S.C. Plant Physiol. (1993) [Pubmed]
  19. S1 destabilization and higher sensitivity to light in metribuzin-resistant mutants. Perewoska, I., Etienne, A.L., Miranda, T., Kirilovsky, D. Plant Physiol. (1994) [Pubmed]
  20. Evidence for different kinases in thylakoid protein phosphorylation. Foyer, C.H. Biochem. J. (1987) [Pubmed]
  21. Expression of the barley psbA gene in Escherichia coli yields a functional in vitro photosystem II protein D1. Efimov, V.A., Fradkov, A.F., Raskind, A.B., Khristin, M.S., Klimov, V.V., Chakhmakhcheva, O.G. FEBS Lett. (1994) [Pubmed]
  22. The clastogenic potential of triazine herbicide combinations found in potable water supplies. Taets, C., Aref, S., Rayburn, A.L. Environ. Health Perspect. (1998) [Pubmed]
  23. Inhibition of cytokine production by the herbicide atrazine. Search for nuclear receptor targets. Devos, S., De Bosscher, K., Staels, B., Bauer, E., Roels, F., Berghe, W., Haegeman, G., Hooghe, R., Hooghe-Peters, E.L. Biochem. Pharmacol. (2003) [Pubmed]
  24. Effects of atrazine on CYP19 gene expression and aromatase activity in testes and on plasma sex steroid concentrations of male African clawed frogs (Xenopus laevis). Hecker, M., Park, J.W., Murphy, M.B., Jones, P.D., Solomon, K.R., Van Der Kraak, G., Carr, J.A., Smith, E.E., du Preez, L., Kendall, R.J., Giesy, J.P. Toxicol. Sci. (2005) [Pubmed]
  25. Analytical performance of accelerator mass spectrometry and liquid scintillation counting for detection of 14C-labeled atrazine metabolites in human urine. Gilman, S.D., Gee, S.J., Hammock, B.D., Vogel, J.S., Haack, K., Buchholz, B.A., Freeman, S.P., Wester, R.C., Hui, X., Maibach, H.I. Anal. Chem. (1998) [Pubmed]
  26. Isotope dilution high-performance liquid chromatography/tandem mass spectrometry method for quantifying urinary metabolites of atrazine, malathion, and 2,4-dichlorophenoxyacetic acid. Beeson, M.D., Driskell, W.J., Barr, D.B. Anal. Chem. (1999) [Pubmed]
  27. Atrazine sensor based on molecularly imprinted polymer-modified gold electrode. Shoji, R., Takeuchi, T., Kubo, I. Anal. Chem. (2003) [Pubmed]
  28. Effects of chloro-s-triazine herbicides and metabolites on aromatase activity in various human cell lines and on vitellogenin production in male carp hepatocytes. Sanderson, J.T., Letcher, R.J., Heneweer, M., Giesy, J.P., van den Berg, M. Environ. Health Perspect. (2001) [Pubmed]
  29. AtzC is a new member of the amidohydrolase protein superfamily and is homologous to other atrazine-metabolizing enzymes. Sadowsky, M.J., Tong, Z., de Souza, M., Wackett, L.P. J. Bacteriol. (1998) [Pubmed]
  30. The atzB gene of Pseudomonas sp. strain ADP encodes the second enzyme of a novel atrazine degradation pathway. Boundy-Mills, K.L., de Souza, M.L., Mandelbaum, R.T., Wackett, L.P., Sadowsky, M.J. Appl. Environ. Microbiol. (1997) [Pubmed]
  31. Novel psbA1 gene from a naturally occurring atrazine-resistant cyanobacterial isolate. Sajjaphan, K., Shapir, N., Judd, A.K., Wackett, L.P., Sadowsky, M.J. Appl. Environ. Microbiol. (2002) [Pubmed]
  32. Environmental xenobiotics may disrupt normal endocrine function by interfering with the binding of physiological ligands to steroid receptors and binding proteins. Danzo, B.J. Environ. Health Perspect. (1997) [Pubmed]
  33. Selection of an atrazine-resistant tobacco cell line having a mutant psbA gene. Sato, F., Shigematsu, Y., Yamada, Y. Mol. Gen. Genet. (1988) [Pubmed]
  34. G-protein-coupled receptor 30 and estrogen receptor-alpha are involved in the proliferative effects induced by atrazine in ovarian cancer cells. Albanito, L., Lappano, R., Madeo, A., Chimento, A., Prossnitz, E.R., Cappello, A.R., Dolce, V., Abonante, S., Pezzi, V., Maggiolini, M. Environ. Health Perspect. (2008) [Pubmed]
  35. Induced new mutation of D1 serine-268 in soybean photosynthetic cell cultures produced atrazine resistance, increased stability of S2QB- and S3QB- states, and increased sensitivity to light stress. Alfonso, M., Pueyo, J.J., Gaddour, K., Etienne, A.L., Kirilovsky, D., Picorel, R. Plant Physiol. (1996) [Pubmed]
  36. Molecularly imprinted solid phase extraction of atrazine from beef liver extracts. Muldoon, M.T., Stanker, L.H. Anal. Chem. (1997) [Pubmed]
  37. An enzyme flow immunoassay that uses beta-galactosidase as the label and a cellobiose dehydrogenase biosensor as the label detector. Burestedt, E., Nistor, C., Schagerlöf, U., Emnéus, J. Anal. Chem. (2000) [Pubmed]
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