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Chemical Compound Review

Thiophos     diethoxy-(4-nitrophenoxy)- sulfanylidene...

Synonyms: Aphamite, Foliclal, Fosferno, Paradust, Thiofos, ...
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Disease relevance of parathion

  • Here, we demonstrate that galantamine, a reversible and centrally acting AChE inhibitor approved for treatment of mild to moderate Alzheimer's disease, protects guinea pigs from the acute toxicity of lethal doses of the nerve agents soman and sarin, and of paraoxon, the active metabolite of the insecticide parathion [1].
  • Polyneuropathy and exposure to parathion [2].
  • Phosphotriesterase, as isolated from Pseudomonas diminuta, is capable of detoxifying widely used pesticides such as paraoxon and parathion and various mammalian acetylcholinesterase inhibitors [3].
  • Parathion hydrolase specified by the Flavobacterium opd gene: relationship between the gene and protein [4].
  • Purification and characterization of a secreted recombinant phosphotriesterase (parathion hydrolase) from Streptomyces lividans [5].

Psychiatry related information on parathion

  • Preweanling rat pups were exposed daily to parathion (1.3 mg/kg or 1.9 mg/kg) or vehicle (corn oil) on postnatal days 5-20, a time period critical to development of behavioral and biochemical parameters of the cholinergic nervous system [6].
  • However, no single measure was the most sensitive across all compounds; for example, the lowest dose of fenthion decreased motor activity by 86% but did not alter the tail-pinch response, whereas the lowest dose of parathion did not lower activity but did decrease the tail-pinch response [7].
  • Water deprivation and food restriction on toxicity of parathion and paraoxon [8].
  • Feeding behavior was inhibited most by exposure to DEF, 2,4-DMA, and methyl parathion [9].
  • Similarly, after administration of several dose levels of parathion in the rat, durations of phases of the maximal electroshock seizure (MES) pattern were altered to the greatest extent 4 hours later, but effects disappeared at 24 hours [10].

High impact information on parathion

  • A genetic polymorphism of paraoxonase (PON) activity which determines high versus low paraoxon hydrolysis in human populations, may determine sensitivity to parathion poisoning [11].
  • Studies indicated that potent, reversible inhibition by ACVTP and the next required deoxynucleoside 5'-triphosphate also occurred when poly(dC)-oligo(dG) or activated calf thymus DNA were used as the template-primer [12].
  • Reduction of the pyridoxal-5'-P enzyme complex in the presence or absence of a deoxynucleoside 5'-triphosphate showed that the alpha subunit possesses five reactive amino groups, one of which is essential for catalytic activity; the beta subunit has three reactive amino groups which are not involved in the deoxynucleoside binding site [13].
  • The complex Rh(cod)(sulfos) (Rh(I); sulfos = (-)O(3)S(C(6)H(4))CH(2)C(CH(2)PPh(2))(3); cod = cycloocta-1,5-diene), either free or supported on silica, does not catalyze the hydrogenation of benzene in either homogeneous or heterogeneous phase [14].
  • Reports of methyl parathion intoxication, usually seen only in field pesticide applicators, have increased throughout the United States as a result of unauthorized application of methyl parathion inside homes [15].

Chemical compound and disease context of parathion


Biological context of parathion


Anatomical context of parathion

  • A similar alteration in the heme moiety of cytochrome P-450 is believed to be responsible, in part, for the loss of monooxygenase activity and cytochrome P-450 seen on incubation of parathion and other thiono-sulfur-containing compounds with hepatic microsomes or a reconstituted cytochrome P-450-containing monooxygenase system [25].
  • Although the incubation of parathion (50 microM) with rat liver microsomes for 10 min led to a 16% decrease in P450 estimated spectrophotometrically, immunoblot analysis revealed no change in the microsomal content of P450 2C11 apoprotein [26].
  • The sizes of cellular deoxynucleoside 5'-triphosphate pools in relation to sensitivity to electron irradiation using sensitive and resistant cell lines [27].
  • Mice were pretreated s.c. with either parathion [a mixed plasma and red blood cell cholinesterase (RBCCh) inhibitor], tetraisopropyl pyrophosphoramide (a selective PCh inhibitor) or placebo, and cholinesterase activity was determined at 24 hr [28].
  • In the present study, human bone marrow cells were exposed in vitro to paraoxon and malaoxon (the primary metabolites of parathion and malathion) [29].

Associations of parathion with other chemical compounds


Gene context of parathion


Analytical, diagnostic and therapeutic context of parathion


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  2. Polyneuropathy and exposure to parathion. Lotti, M., Becker, C.E. Neurology (1982) [Pubmed]
  3. Three-dimensional structure of the binuclear metal center of phosphotriesterase. Benning, M.M., Kuo, J.M., Raushel, F.M., Holden, H.M. Biochemistry (1995) [Pubmed]
  4. Parathion hydrolase specified by the Flavobacterium opd gene: relationship between the gene and protein. Mulbry, W.W., Karns, J.S. J. Bacteriol. (1989) [Pubmed]
  5. Purification and characterization of a secreted recombinant phosphotriesterase (parathion hydrolase) from Streptomyces lividans. Rowland, S.S., Speedie, M.K., Pogell, B.M. Appl. Environ. Microbiol. (1991) [Pubmed]
  6. Behavioral and biochemical effects of postnatal parathion exposure in the rat. Stamper, C.R., Balduini, W., Murphy, S.D., Costa, L.G. Neurotoxicology and teratology. (1988) [Pubmed]
  7. Comparisons of the acute effects of cholinesterase inhibitors using a neurobehavioral screening battery in rats. Moser, V.C. Neurotoxicology and teratology. (1995) [Pubmed]
  8. Water deprivation and food restriction on toxicity of parathion and paraoxon. Baetjer, A.M. Arch. Environ. Health (1983) [Pubmed]
  9. Behavioral indicators of sublethal toxicity in rainbow trout. Little, E.E., Archeski, R.D., Flerov, B.A., Kozlovskaya, V.I. Arch. Environ. Contam. Toxicol. (1990) [Pubmed]
  10. Some aspects of neurophysiological basis of insecticide action. Woolley, D.E. Fed. Proc. (1976) [Pubmed]
  11. The molecular basis of the human serum paraoxonase activity polymorphism. Humbert, R., Adler, D.A., Disteche, C.M., Hassett, C., Omiecinski, C.J., Furlong, C.E. Nat. Genet. (1993) [Pubmed]
  12. Herpes simplex virus type 1 DNA polymerase. Mechanism of inhibition by acyclovir triphosphate. Reardon, J.E., Spector, T. J. Biol. Chem. (1989) [Pubmed]
  13. Inactivation of avian myeloblastosis virus DNA polymerase by specific binding of pyridoxal 5'-phosphate to deoxynucleoside triphosphate binding site. Papas, T.S., Pry, T.W., Marciani, D.J. J. Biol. Chem. (1977) [Pubmed]
  14. Hydrogenation of arenes over silica-supported catalysts that combine a grafted rhodium complex and palladium nanoparticles: evidence for substrate activation on Rh(single-site)-Pd(metal) moieties. Barbaro, P., Bianchini, C., Dal Santo, V., Meli, A., Moneti, S., Psaro, R., Scaffidi, A., Sordelli, L., Vizza, F. J. Am. Chem. Soc. (2006) [Pubmed]
  15. Methyl parathion: a review of health effects. Garcia, S.J., Abu-Qare, A.W., Meeker-O'Connell, W.A., Borton, A.J., Abou-Donia, M.B. Journal of toxicology and environmental health. Part B, Critical reviews. (2003) [Pubmed]
  16. Interaction of ethanol and the organophosphorus insecticide parathion. O'Shaughnessy, J.A., Sultatos, L.G. Biochem. Pharmacol. (1995) [Pubmed]
  17. Carboxylesterase and A-esterase activities during maturation and aging: relationship to the toxicity of chlorpyrifos and parathion in rats. Karanth, S., Pope, C. Toxicol. Sci. (2000) [Pubmed]
  18. An integrated addition and interaction model for assessing toxicity of chemical mixtures. Rider, C.V., LeBlanc, G.A. Toxicol. Sci. (2005) [Pubmed]
  19. Optical microbial biosensor for detection of methyl parathion pesticide using Flavobacterium sp. whole cells adsorbed on glass fiber filters as disposable biocomponent. Kumar, J., Jha, S.K., D'Souza, S.F. Biosensors & bioelectronics. (2006) [Pubmed]
  20. 2',3'-Didehydro-3'-deoxythymidine: regulation of its metabolic activation by modulators of thymidine-5'-triphosphate biosynthesis. Ahluwalia, G.S., Gao, W.Y., Mitsuya, H., Johns, D.G. Mol. Pharmacol. (1996) [Pubmed]
  21. Immobilized parathion hydrolase: an amperometric sensor for parathion. Sacks, V., Eshkenazi, I., Neufeld, T., Dosoretz, C., Rishpon, J. Anal. Chem. (2000) [Pubmed]
  22. Biotransformation of parathion in human liver: participation of CYP3A4 and its inactivation during microsomal parathion oxidation. Butler, A.M., Murray, M. J. Pharmacol. Exp. Ther. (1997) [Pubmed]
  23. Strategies, systems, value judgements and dieldrin in control of locust hoppers. Gunn, D.L. Philos. Trans. R. Soc. Lond., B, Biol. Sci. (1979) [Pubmed]
  24. Transposon-like organization of the plasmid-borne organophosphate degradation (opd) gene cluster found in Flavobacterium sp. Siddavattam, D., Khajamohiddin, S., Manavathi, B., Pakala, S.B., Merrick, M. Appl. Environ. Microbiol. (2003) [Pubmed]
  25. Inhibition of rat liver cytochrome P-450 by benzyl hydrodisulfide. Sawahata, T., Neal, R.A. Mol. Pharmacol. (1982) [Pubmed]
  26. Inhibition and inactivation of constitutive cytochromes P450 in rat liver by parathion. Butler, A.M., Murray, M. Mol. Pharmacol. (1993) [Pubmed]
  27. The sizes of cellular deoxynucleoside 5'-triphosphate pools in relation to sensitivity to electron irradiation using sensitive and resistant cell lines. Booth, J.A., Ockey, C.H., Saffhill, R. Carcinogenesis (1987) [Pubmed]
  28. Decreased plasma cholinesterase activity enhances cocaine toxicity in mice. Hoffman, R.S., Henry, G.C., Wax, P.M., Weisman, R.S., Howland, M.A., Goldfrank, L.R. J. Pharmacol. Exp. Ther. (1992) [Pubmed]
  29. Inhibition of human bone marrow-derived stem cell colony formation (CFU-E, BFU-E, and CFU-GM) following in vitro exposure to organophosphates. Gallicchio, V.S., Casale, G.P., Watts, T. Exp. Hematol. (1987) [Pubmed]
  30. Role of genetic polymorphism of human plasma paraoxonase/arylesterase in hydrolysis of the insecticide metabolites chlorpyrifos oxon and paraoxon. Furlong, C.E., Richter, R.J., Seidel, S.L., Motulsky, A.G. Am. J. Hum. Genet. (1988) [Pubmed]
  31. Activation of phosphorothionate pesticides based on a cytochrome P450 BM-3 (CYP102 A1) mutant for expanded neurotoxin detection in food using acetylcholinesterase biosensors. Schulze, H., Schmid, R.D., Bachmann, T.T. Anal. Chem. (2004) [Pubmed]
  32. Percutaneous penetration of three insecticides in rats: a comparison of two methods for in vivo determination. Shah, P.V., Guthrie, F.E. J. Invest. Dermatol. (1983) [Pubmed]
  33. Heterogeneity of the glutathione transferase genes encoding enzymes responsible for insecticide degradation in the housefly. Syvanen, M., Zhou, Z., Wharton, J., Goldsbury, C., Clark, A. J. Mol. Evol. (1996) [Pubmed]
  34. Polyacrylamide gel electrophoresis of rat brain acetylcholinesterase: isoenzyme changes following parathion poisoning. Vijayan, V.K., Brownson, R.H. J. Neurochem. (1975) [Pubmed]
  35. Exposure of neonatal rats to parathion elicits sex-selective reprogramming of metabolism and alters the response to a high-fat diet in adulthood. Lassiter, T.L., Ryde, I.T., Mackillop, E.A., Brown, K.K., Levin, E.D., Seidler, F.J., Slotkin, T.A. Environ. Health Perspect. (2008) [Pubmed]
  36. Exposure of neonatal rats to parathion elicits sex-selective impairment of acetylcholine systems in brain regions during adolescence and adulthood. Slotkin, T.A., Bodwell, B.E., Ryde, I.T., Levin, E.D., Seidler, F.J. Environ. Health Perspect. (2008) [Pubmed]
  37. The role of metabolism in determining susceptibility to parathion toxicity in man. Mutch, E., Blain, P.G., Williams, F.M. Toxicol. Lett. (1999) [Pubmed]
  38. Do multiple cytochrome P450 isoforms contribute to parathion metabolism in man? Mutch, E., Daly, A.K., Leathart, J.B., Blain, P.G., Williams, F.M. Arch. Toxicol. (2003) [Pubmed]
  39. Flavonoid-induced alterations in cytochrome P450-dependent biotransformation of the organophosphorus insecticide parathion in the mouse. Ramos, S., Sultatos, L. Toxicology (1998) [Pubmed]
  40. Determination of ethyl and methyl parathion in runoff water with high performance liquid chromatography. Paschal, D.C., Bicknell, R., Dresbach, D. Anal. Chem. (1977) [Pubmed]
  41. A study of the binding of sulfur to rat liver microsomes which occurs concurrently with the metabolism of O, O-diethyl O-p-nitrophenyl phosphorothioate (parathion) to O, O-diethyl O-p-nitrophenyl phosphate (paraoxon). Davis, J.E., Mende, T.J. J. Pharmacol. Exp. Ther. (1977) [Pubmed]
  42. Painless acute pancreatitis subsequent to anticholinesterase insecticide (parathion) intoxication. Lankisch, P.G., Müller, C.H., Niederstadt, H., Brand, A. Am. J. Gastroenterol. (1990) [Pubmed]
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