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Chemical Compound Review

Cipotril     4-hydroxy-3,5-diiodo- benzonitrile

Synonyms: Actrilawn, BANTROL, Bentrol, Certrol, Ioxynil, ...
 
 
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Disease relevance of Ioxynil

  • The relation between blood chlorophenoxy herbicide and ioxynil concentrations and toxicity, and the effect of alkaline diuresis on outcome, have been studied in 41 patients [1].
  • However, only a fungal isolate (Fusarium solani) and a Gram-negative bacterium (Klebsiella ozaenae) released 14CO2 from ring-labeled ioxynil [2].
  • A patient who died in asystole less than 18 h after ingestion of 'Clovercide Extra', a combination hormonal weedkiller containing ioxynil and 4-chloro-2-methyl phenoxypropionic acid, is described [3].
  • A new ioxynil-resistant mutant in Synechocystis PCC 6714: hypothesis on the interaction of ioxynil with the D 1 protein [4].
  • Delayed sudden death after ingestion of MCPP and ioxynil: an unusual presentation of hormonal weedkiller intoxication [3].
 

High impact information on Ioxynil

  • 7 of 11 patients who had co-ingested ioxynil died; 3 had alkaline diuresis and all survived [1].
  • Alkaline diuresis should be used to treat acute poisoning with chlorophenoxy herbicides or ioxynil in the presence of coma or other poor prognostic indicators, such as acidaemia, or if plasma total chlorophenoxy concentrations are 0.5 g/l or more [1].
  • HPLC measurement of chlorophenoxy herbicides, bromoxynil, and ioxynil, in biological specimens to aid diagnosis of acute poisoning [5].
  • When RBCs were cultured with 10 nM T3 at 25 degrees C for 2 days in the presence of monodansylcadaverine, ethinylestradiol, ioxynil or dicofol at the defined concentrations, these compounds inhibited significantly the induction of the thyroid hormone receptor alpha gene by T3 [6].
  • Ioxynil bound to TBPA but not to TBG nor albumin [7].
 

Chemical compound and disease context of Ioxynil

 

Biological context of Ioxynil

 

Anatomical context of Ioxynil

  • Ioxynil, an iodine-containing compound with structural similarity to T3 affects the thyroids of experimental animals [7].
 

Gene context of Ioxynil

  • The mutation found in the psbA gene (encoding the D 1 photosystem II protein) is at the same codon 266 as for the first ioxynil-resistant mutant IoxIA previously selected [G. Ajlani, I. Meyer, C. Vernotte, and C. Astier, FEBS Lett. 246, 207-210 (1989)] [4].

References

  1. Alkaline diuresis for acute poisoning with chlorophenoxy herbicides and ioxynil. Flanagan, R.J., Meredith, T.J., Ruprah, M., Onyon, L.J., Liddle, A. Lancet (1990) [Pubmed]
  2. Isolation of ioxynil degraders from soil-enrichment cultures. Hsu, J.C., Camper, N.D. Can. J. Microbiol. (1976) [Pubmed]
  3. Delayed sudden death after ingestion of MCPP and ioxynil: an unusual presentation of hormonal weedkiller intoxication. Dickey, W., McAleer, J.J., Callender, M.E. Postgraduate medical journal. (1988) [Pubmed]
  4. A new ioxynil-resistant mutant in Synechocystis PCC 6714: hypothesis on the interaction of ioxynil with the D 1 protein. Creuzet, S., Ajlani, G., Vernotte, C., Astier, C. Z. Naturforsch., C, J. Biosci. (1990) [Pubmed]
  5. HPLC measurement of chlorophenoxy herbicides, bromoxynil, and ioxynil, in biological specimens to aid diagnosis of acute poisoning. Flanagan, R.J., Ruprah, M. Clin. Chem. (1989) [Pubmed]
  6. Characteristics of 3,5,3'-triiodothyronine (T3)-uptake system of tadpole red blood cells: effect of endocrine-disrupting chemicals on cellular T3 response. Shimada, N., Yamauchi, K. J. Endocrinol. (2004) [Pubmed]
  7. Ioxynil and 3,5,3'-triiodothyronine: comparison of binding to human plasma proteins. Ogilvie, L.M., Ramsden, D.B. Toxicol. Lett. (1988) [Pubmed]
  8. Bioaccumulation and toxicity of sediment associated herbicides (ioxynil, pendimethalin, and bentazone) in Lumbriculus variegatus (Oligochaeta) and Chironomus riparius (Insecta). Mäenpää, K.A., Sormunen, A.J., Kukkonen, J.V. Ecotoxicol. Environ. Saf. (2003) [Pubmed]
  9. [125I]azido-ioxynil labels Val249 of the photosystem II D-1 reaction center protein. Oettmeier, W., Masson, K., Höhfeld, J., Meyer, H.E., Pfister, K., Fischer, H.P. Z. Naturforsch., C, J. Biosci. (1989) [Pubmed]
 
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