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Chemical Compound Review

Pyrethroids     (5-benzyl-3-furyl)methyl 2,2-dimethyl-3-(2...

Synonyms: Chrysron, Enforcer, Premgard, Synthrin, Chryson, ...
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Disease relevance of Pyrethroids


Psychiatry related information on Pyrethroids


High impact information on Pyrethroids

  • It is now well established that severe neurological symptoms of poisoning with pyrethroids and DDT in mammals and insects are the result of modification of Na+ channel activity [8].
  • The binding occurs on the Na+ channel at a binding site distinct from that of other gating system toxins like batrachotoxin, veratridine, grayanotoxin, aconitine, and pyrethroids [9].
  • Although the use of pyrethroids is increasing, the specific enzymes involved in the hydrolysis of these insecticides have yet to be identified [1].
  • A second carboxylesterase gene (NCBI accession number NM_133960), isolated during a cDNA mouse liver library screening, was also found to hydrolyze pyrethroids [1].
  • The synthetic pyrethroids offer many advantages for veterinary and public health use, particularly their selectivity, high toxicity to insects, and relative lack of chronic effects [10].

Chemical compound and disease context of Pyrethroids


Biological context of Pyrethroids

  • Since action potentials in these nerves are carried by calcium ions through TTX-insensitive voltage-gated cation channels, these findings provide evidence that pyrethroids can alter neuronal excitability through an action on voltage-sensitive channels other than the sodium channel [15].
  • We demonstrate that pyrethroids, in addition to their neurotoxic effect, induce oxidative stress and lipid peroxidation in insects [16].
  • Peroxidase activity of the recombinant nlgst1-1 indicated that it had a role in resistance, through detoxification of lipid peroxidation products induced by pyrethroids [17].
  • Spheroids were left intact for different time periods to assess the effect of radiation crossfire on cell death [18].
  • However, in extending usage to agricultural pest control, much more extensive investigations should be forthcoming from both chemical and biological aspects, since there is scant information on the fate of these pyrethroids in the environment [19].

Anatomical context of Pyrethroids

  • Here, we show that an F-to-I substitution at 1519 (F1519I) in segment 6 of domain III (IIIS6) abolished the sensitivity of the cockroach sodium channel expressed in Xenopus laevis oocytes to all eight structurally diverse pyrethroids examined, including permethrin and deltamethrin [20].
  • Insect neurosecretory neurons are sensitive to very low concentrations of pyrethroids, and disruption of the neuroendocrine system has been implicated as a factor contributing to the irreversible effects of pyrethroid intoxication in insects [15].
  • The three pyrethroids tested all inhibited the transfer of Lucifer Yellow CH between WB-F344 rat liver epithelial cells in culture, supporting the increase of GGT-positive foci and suggesting that these substances can act as tumour promoters [21].
  • Pyrethroid displacement of specific [3H]Ro5-4864 binding to rat brain membranes was investigated to further define the interaction of pyrethroids with the PTBR [22].
  • The phenoxybenzyl pyrethroids also increased the spontaneous release of [3H]acetylcholine from rat brain synaptosomes, further supporting a depolarizing action of these insecticides on nerve terminal membranes [23].

Associations of Pyrethroids with other chemical compounds


Gene context of Pyrethroids


Analytical, diagnostic and therapeutic context of Pyrethroids

  • The abdominal nerve cords and neuromuscular preparations isolated from the crayfish are convenient materials for bioassay of certain environmental toxicants such as pyrethroids, chlorinated hydrocarbons, and other insecticides [33].
  • Multi-residue matrix solid-phase dispersion method for the determination of six synthetic pyrethroids in vegetables followed by gas chromatography with electron capture detection [34].
  • Determination of residues of synthetic pyrethroids in fruit and vegetables by gas - liquid and high-performance liquid chromatography [35].
  • New born babies and children are often exposed to pyrethroids for long periods by the use of liquid vaporizers [36].
  • PCR and sequencing was undertaken only on individuals that were demonstrated to be phenotypically nerve insensitive or susceptible to pyrethroids using a neurophysiological technique [37].


  1. Identification, expression, and purification of a pyrethroid-hydrolyzing carboxylesterase from mouse liver microsomes. Stok, J.E., Huang, H., Jones, P.D., Wheelock, C.E., Morisseau, C., Hammock, B.D. J. Biol. Chem. (2004) [Pubmed]
  2. Ciguatoxin is a novel type of Na+ channel toxin. Bidard, J.N., Vijverberg, H.P., Frelin, C., Chungue, E., Legrand, A.M., Bagnis, R., Lazdunski, M. J. Biol. Chem. (1984) [Pubmed]
  3. Neurotoxicological effects and the mode of action of pyrethroid insecticides. Vijverberg, H.P., van den Bercken, J. Crit. Rev. Toxicol. (1990) [Pubmed]
  4. Retroviruses under editing crossfire: a second member of the human APOBEC3 family is a Vif-blockable innate antiretroviral factor. Trono, D. EMBO Rep. (2004) [Pubmed]
  5. Programmed neuronal death in sepsis: caught in a crossfire or a planned sacrifice? Young, G.B. Crit. Care Med. (2004) [Pubmed]
  6. Relative potencies for acute effects of pyrethroids on motor function in rats. Wolansky, M.J., Gennings, C., Crofton, K.M. Toxicol. Sci. (2006) [Pubmed]
  7. Toxicity of microencapsulated permethrin to selected nontarget aquatic invertebrates. Sibley, P.K., Kaushik, N.K. Arch. Environ. Contam. Toxicol. (1991) [Pubmed]
  8. Nerve membrane Na+ channels as targets of insecticides. Narahashi, T. Trends Pharmacol. Sci. (1992) [Pubmed]
  9. Binding of sea anemone toxin to receptor sites associated with gating system of sodium channel in synaptic nerve endings in vitro. Vincent, J.P., Balerna, M., Barhanin, J., Fosset, M., Lazdunski, M. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  10. Mechanisms of resistance to pyrethroid insecticides. Miller, T.A. Parasitol. Today (Regul. Ed.) (1988) [Pubmed]
  11. Transformation of synthetic pyrethroid insecticides by a thermophilic Bacillus sp. Maloney, S.E., Maule, A., Smith, A.R. Arch. Microbiol. (1992) [Pubmed]
  12. Development of toxicity identification evaluation procedures for pyrethroid detection using esterase activity. Wheelock, C.E., Miller, J.L., Miller, M.J., Gee, S.J., Shan, G., Hammock, B.D. Environ. Toxicol. Chem. (2004) [Pubmed]
  13. Toxicity of natural pyrethrins and five pyrethroids to fish. Mauck, W.L., Olson, L.E. Arch. Environ. Contam. Toxicol. (1976) [Pubmed]
  14. Comparative study on the environmental risk induced by several pyrethroids in estuarine and freshwater invertebrate organisms. Sánchez-Fortún, S., Barahona, M.V. Chemosphere (2005) [Pubmed]
  15. Neurotoxic actions of pyrethroid insecticides. Soderlund, D.M., Bloomquist, J.R. Annu. Rev. Entomol. (1989) [Pubmed]
  16. Glutathione S-transferases as antioxidant defence agents confer pyrethroid resistance in Nilaparvata lugens. Vontas, J.G., Small, G.J., Hemingway, J. Biochem. J. (2001) [Pubmed]
  17. Purification, molecular cloning and heterologous expression of a glutathione S-transferase involved in insecticide resistance from the rice brown planthopper, Nilaparvata lugens. Vontas, J.G., Small, G.J., Nikou, D.C., Ranson, H., Hemingway, J. Biochem. J. (2002) [Pubmed]
  18. A gene therapy/targeted radiotherapy strategy for radiation cell kill by. Boyd, M., Mairs, R.J., Cunningham, S.H., Mairs, S.C., McCluskey, A., Livingstone, A., Stevenson, K., Brown, M.M., Wilson, L., Carlin, S., Wheldon, T.E. The journal of gene medicine. (2001) [Pubmed]
  19. Degradation, metabolism and toxicity of synthetic pyrethroids. Miyamoto, J. Environ. Health Perspect. (1976) [Pubmed]
  20. Identification of amino acid residues in the insect sodium channel critical for pyrethroid binding. Tan, J., Liu, Z., Wang, R., Huang, Z.Y., Chen, A.C., Gurevitz, M., Dong, K. Mol. Pharmacol. (2005) [Pubmed]
  21. Enhancement of altered hepatic foci in rat liver and inhibition of intercellular communication in vitro by the pyrethroid insecticides fenvalerate, flucythrinate and cypermethrin. Hemming, H., Flodström, S., Wärngård, L. Carcinogenesis (1993) [Pubmed]
  22. Involvement of peripheral-type benzodiazepine receptors in the proconvulsant actions of pyrethroid insecticides. Devaud, L.L., Murray, T.F. J. Pharmacol. Exp. Ther. (1988) [Pubmed]
  23. Pyrethroid insecticide-induced alterations in mammalian synaptic membrane potential. Eells, J.T., Bandettini, P.A., Holman, P.A., Propp, J.M. J. Pharmacol. Exp. Ther. (1992) [Pubmed]
  24. Mutations of the para sodium channel of Drosophila melanogaster identify putative binding sites for pyrethroids. Vais, H., Atkinson, S., Pluteanu, F., Goodson, S.J., Devonshire, A.L., Williamson, M.S., Usherwood, P.N. Mol. Pharmacol. (2003) [Pubmed]
  25. Dependence on gamma-aminobutyric acid of pyrethroid and 4'-chlorodiazepam modulation of the binding of t-[35S]butylbicyclophosphorothionate in piscine brain. Eshleman, A.J., Murray, T.F. Neuropharmacology (1990) [Pubmed]
  26. A sensitive class specific immunoassay for the detection of pyrethroid metabolites in human urine. Shan, G., Huang, H., Stoutamire, D.W., Gee, S.J., Leng, G., Hammock, B.D. Chem. Res. Toxicol. (2004) [Pubmed]
  27. Induction of cytochrome P450 2B1 by pyrethroids in primary rat hepatocyte cultures. Heder, A.F., Hirsch-Ernst, K.I., Bauer, D., Kahl, G.F., Desel, H. Biochem. Pharmacol. (2001) [Pubmed]
  28. Determination of pyrethroid residues on paddy rice by reversed-phase high-performance liquid chromatography. Haddad, P.R., Brayan, J.G., Sharp, G.J., Dilli, S., Desmarchelier, J.M. J. Chromatogr. (1989) [Pubmed]
  29. Point mutations in the Drosophila sodium channel gene para associated with resistance to DDT and pyrethroid insecticides. Pittendrigh, B., Reenan, R., ffrench-Constant, R.H., Ganetzky, B. Mol. Gen. Genet. (1997) [Pubmed]
  30. Pyrethroid insecticides influence the signal transduction in T helper lymphocytes from atopic and nonatopic subjects. Diel, F., Horr, B., Borck, H., Irman-Florjanc, T. Inflamm. Res. (2003) [Pubmed]
  31. The binding properties of pyrethroids to human skin fibroblast androgen receptors and to sex hormone binding globulin. Eil, C., Nisula, B.C. J. Steroid Biochem. (1990) [Pubmed]
  32. Lack of significant estrogenic or antiestrogenic activity of pyrethroid insecticides in three in vitro assays based on classic estrogen receptor alpha-mediated mechanisms. Saito, K., Tomigahara, Y., Ohe, N., Isobe, N., Nakatsuka, I., Kaneko, H. Toxicol. Sci. (2000) [Pubmed]
  33. Nerve membrane ion channels as the target site of environmental toxicants. Narahashi, T. Environ. Health Perspect. (1987) [Pubmed]
  34. Multi-residue matrix solid-phase dispersion method for the determination of six synthetic pyrethroids in vegetables followed by gas chromatography with electron capture detection. Ling, Y.C., Huang, I.P. Journal of chromatography. A. (1995) [Pubmed]
  35. Determination of residues of synthetic pyrethroids in fruit and vegetables by gas - liquid and high-performance liquid chromatography. Baker, P.G., Bottomley, P. The Analyst. (1982) [Pubmed]
  36. Mosquito repellent (pyrethroid-based) induced dysfunction of blood-brain barrier permeability in developing brain. Sinha, C., Agrawal, A.K., Islam, F., Seth, K., Chaturvedi, R.K., Shukla, S., Seth, P.K. Int. J. Dev. Neurosci. (2004) [Pubmed]
  37. Novel mutations in the para-homologous sodium channel gene associated with phenotypic expression of nerve insensitivity resistance to pyrethroids in Heliothine lepidoptera. Head, D.J., McCaffery, A.R., Callaghan, A. Insect Mol. Biol. (1998) [Pubmed]
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