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Chemical Compound Review

LEPTOPHOS     (4-bromo-2,5-dichloro- phenoxy)-methoxy...

Synonyms: Phosvel, Fosvel, Oleophosvel, Abar, MBCP, ...
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Disease relevance of LEPTOPHOS

  • The results indicated that leptophos induced severe ataxia and paralysis in sheep following about 4 months of treatment [1].
  • Separation and toxicity of enantiomers of organophosphorus insecticide leptophos [2].
  • Recent investigation into a possible association between exposure to Leptophos and neurological symptoms in insecticide factory workers makes study of the neurological effects of Leptophos in the experimental situation particularly important [3].
  • The neurodegenerative properties of the organophosphate ester leptophos (LEP) and the carbamate ester carbaryl (CB), both of which can cause neuropathic effects in animals, were investigated in differentiating mouse N2a neuroblastoma cells [4].
  • Delayed neurotoxicity induced by leptophos, an organophosphorus insecticide, was intensified in hens when phenylmethylsulfonyl fluoride (PMSF) at dose of 30, 60, and 120 mg/kg body weight was administered at different time intervals (24 hr, 3 days, and 5 days) for each dose of PMSF after the hens were exposed to 30 mg/kg (i.v.) of leptophos [5].

High impact information on LEPTOPHOS

  • A comparison of the bimolecular rate constants (ki) for inhibition of electric eel acetylcholinesterase (AChE) by the oxono (i.e., P=O) and thiono (i.e., P=S) analogues of parathion, methylparathion, leptophos, fonofos, sarin, and soman revealed that the oxono/thiono ratios of ki values varied from 14 for soman to 1240 for parathion [6].
  • TOCP (10 to 100 mg/kg), leptophos (25 to 150 mg/kg), and DBDCV (1.0 to 4.0 mg/kg) inhibited both brain and lymphocyte NTE activity in a dose-related manner with good correlation of inhibition between tissues taken 24 hr after exposure (r2 = 0.53 to 0.67; p less than 0.020 to 0.001) [7].
  • In the case of leptophos-treated sheep, numerous prominent degenerative lesions of axons were observed in spinal cords and brains [1].
  • Metabolism and pharmacokinetics of a single oral dose of O-4-bromo-2,5-dichlorophenyl O-methyl phenylphosphonothioate (Leptophos) in hens [8].
  • Residues of phosvel in plasma and in adipose tissue of hens after single oral administration [9].

Chemical compound and disease context of LEPTOPHOS


Biological context of LEPTOPHOS


Anatomical context of LEPTOPHOS

  • Radioactive carbaryl, carbofuran, parathion, leptophos, and DDT were added to cigarettes and the mainstream smoke was directed to the lungs of rats via the trachea [15].
  • No difference was observed in the sensitivity of flyhead and thorax acetylcholinesterase to leptophos-oxon in vitro, and tolerance to leptophos by the resistant strain is explained in terms of decreased rates or penetration and minor differences in metabolism [16].
  • Assuming that Leptophos resembles TOCP in this regard, peripheral nerve damage would be the expected earliest change, especially in the low-dose situation in the human [3].
  • On the contrary, the evident accumulation of leptophos was observed in only sciatic nerve with RIVInj [17].
  • Leptophos in laid egg yolk was detected every day for 10 days, and the highest concentration of leptophos in egg yolk was observed on the 6th day after administration to hens [18].

Associations of LEPTOPHOS with other chemical compounds


Gene context of LEPTOPHOS

  • Inhibition of neurite outgrowth in N2a cells by leptophos and carbaryl: effects on neurofilament heavy chain, GAP-43 and HSP-70 [4].
  • In comparing neurotoxic esterase (NTE) inhibition properties of a series of phenylphosphonates, it was discovered that certain compounds including leptophos inhibited mipafox-insensitive phenylvalerate hydrolases [19].
  • Leptophos is a potent acetylcholinesterase inhibitor which causes delayed central-peripheral neuropathy [21].
  • For EPN and leptophos, bromine activation resulted in greater inhibition of NTE than RLM [22].
  • Enzyme assays of CNP revealed a decrease in brain CNP activity at the time of maximal locomotor impairment after a single, oral dose of leptophos [23].

Analytical, diagnostic and therapeutic context of LEPTOPHOS


  1. Six-month daily treatment of sheep with neurotoxic organophosphorus compounds. Soliman, S.A., Svendsgaard, D., Farmer, J.D., Curley, A., Durham, W.F. Toxicol. Appl. Pharmacol. (1983) [Pubmed]
  2. Separation and toxicity of enantiomers of organophosphorus insecticide leptophos. Yen, J.H., Tsai, C.C., Wang, Y.S. Ecotoxicol. Environ. Saf. (2003) [Pubmed]
  3. The neuropathology of leptophos in the hen: a chronologic study. Preissig, S.H., Abou-Donia, M.B. Environmental research. (1978) [Pubmed]
  4. Inhibition of neurite outgrowth in N2a cells by leptophos and carbaryl: effects on neurofilament heavy chain, GAP-43 and HSP-70. Sachana, M., Flaskos, J., Alexaki, E., Hargreaves, A.J. Toxicology in vitro : an international journal published in association with BIBRA. (2003) [Pubmed]
  5. Effects of various post-treatment by phenylmethylsulfonyl fluoride on delayed neurotoxicity induced by leptophos. Piao, F.Y., Kitabatake, M., Xie, X.K., Yamauchi, T. The Journal of toxicological sciences. (1995) [Pubmed]
  6. Quantitative structure-activity analysis of acetylcholinesterase inhibition by oxono and thiono analogues of organophosphorus compounds. Maxwell, D.M., Brecht, K.M. Chem. Res. Toxicol. (1992) [Pubmed]
  7. Lymphocyte and brain neurotoxic esterase: dose and time dependence of inhibition in the hen examined with three organophosphorus esters. Schwab, B.W., Richardson, R.J. Toxicol. Appl. Pharmacol. (1986) [Pubmed]
  8. Metabolism and pharmacokinetics of a single oral dose of O-4-bromo-2,5-dichlorophenyl O-methyl phenylphosphonothioate (Leptophos) in hens. Abou-Donia, M.B. Toxicol. Appl. Pharmacol. (1980) [Pubmed]
  9. Residues of phosvel in plasma and in adipose tissue of hens after single oral administration. Konno, N., Kinebuchi, H. Toxicol. Appl. Pharmacol. (1978) [Pubmed]
  10. Neurotoxicity of organophosphorus insecticides Leptophos and EPN. El-Sebae, A.H., Soliman, S.A., Elamayem, M.A., Ahmed, N.S. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. (1977) [Pubmed]
  11. In-vivo interaction of some organophosphorus insecticides with different biochemical targets in white rats. Enan, E.E., El-Sebae, A.H., Enan, O.H., El-Fiki, S. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. (1982) [Pubmed]
  12. Immunological surveillance and toxicity in mice exposed to the organophosphate pesticide, leptophos. Koller, L.D., Exon, J.H., Roan, J.G. Environmental research. (1976) [Pubmed]
  13. Chemistry and toxicology of pesticide chemicals. II. Stability of leptophos. Zayed, S., Fakhr, I.M., Hassan, A. Environmental quality and safety. Supplement. (1975) [Pubmed]
  14. Inhibition of mitochondrial electron transport systems by phosvel and some environmental conversion products. Winston, G.W., Pardini, R. Bulletin of environmental contamination and toxicology. (1976) [Pubmed]
  15. Nature and fate of insecticide residues inhaled by rats in cigarette smoke. Atallah, Y.H., Dorough, H.W., Thorstenson, J.H. Drug Metab. Dispos. (1975) [Pubmed]
  16. Penetration and comparative metabolism of leptophos in susceptible and resistant houseflies. Lee, P.W., Fukuto, T.R. Arch. Environ. Contam. Toxicol. (1976) [Pubmed]
  17. Delayed neurotoxicity and toxicokinetics of leptophos in hens given repeatedly by low-dose intravenous injections. Yamauchi, T., Katoh, K., Konno, N., Fukushima, M. The Journal of toxicological sciences. (1989) [Pubmed]
  18. Transfer of leptophos in hen eggs and tissues of embryonic rats. Piao, F.Y., Xie, X.K., Kitabatake, M., Yamauchi, T. The Journal of toxicological sciences. (1997) [Pubmed]
  19. In vitro neurotoxic esterase assay using leptophos oxon analogs as inhibitors. Reinders, J.H., Hansen, L.G., Metcalf, R.L. Toxicol. Lett. (1983) [Pubmed]
  20. Inhibitory effect of leptophos on carboxylesterase (isocarboxazid amidase) in rat liver. Moroi, K., Kuga, T. Toxicol. Lett. (1982) [Pubmed]
  21. Effects of leptophos on rat brain levels and turnover rates of biogenic amines and their metabolites. Aldous, C.N., Farr, C.H., Sharma, R.P. Ecotoxicol. Environ. Saf. (1982) [Pubmed]
  22. Comparative effectiveness of organophosphorus protoxicant activating systems in neuroblastoma cells and brain homogenates. Barber, D., Correll, L., Ehrich, M. J. Toxicol. Environ. Health Part A (1999) [Pubmed]
  23. Effect of acute organophosphorus exposure on 2', 3',-cyclic nucleotide 3'-phosphohydrolase activity in hen neural tissue. Olajos, E.J., Shopp, G., Rosenblum, I. Neurotoxicology (1982) [Pubmed]
  24. Delayed neurotoxicity from continous low-dose oral administration of leptophos to hens. Abou-Donia, M.B., Preissig, S.H. Toxicol. Appl. Pharmacol. (1976) [Pubmed]
  25. Delayed neurotoxicity from long-term low-level topical administration of leptophos to the comb of hens. Abou-Donia, M.B., Graham, D.G. Toxicol. Appl. Pharmacol. (1978) [Pubmed]
  26. Effects of prednisolone and complex of vitamin B1, B2, B6 and B12 on organophosphorus compound-induced delayed neurotoxicity. Piao, F., Ma, N., Yamamoto, H., Yamauchi, T., Yokoyama, K. Journal of occupational health. (2004) [Pubmed]
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