Metrifonate

Source: Wikipedia, the free encyclopedia.
Metrifonate
QP53AF02 (WHO)
Pharmacokinetic data
Elimination half-life3 hours
Identifiers
  • (RS)-Dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate
JSmol)
ChiralityRacemic mixture
  • COP(=O)(C(C(Cl)(Cl)Cl)O)OC
  • InChI=1S/C4H8Cl3O4P/c1-10-12(9,11-2)3(8)4(5,6)7/h3,8H,1-2H3 ☒N
  • Key:NFACJZMKEDPNKN-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Metrifonate (

INN) or trichlorfon (USAN) is an irreversible organophosphate acetylcholinesterase inhibitor.[3] It is a prodrug which is activated non-enzymatically into the active agent dichlorvos
.

It is used as an insecticide. According to the US

harvester ants.[5]

It can be used to treat schistosomiasis[6] caused by Schistosoma haematobium,[7] but is no longer commercially available.[8]

It has been proposed for use in treatment of Alzheimer's disease, but use for that purpose is not currently recommended.[9]

Bans and restrictions

In the United States, trichlorfon/metrifonate may only be used on nonfood and nonfeed sites.[10]

Trichlorfon/metrifonate was banned in the

EU in 2008 (Regulation (EC) 689/2008) and in Brazil in 2010.[11]

Trichlorfon/metrifonate was banned in Argentina in 2018,[12] noting that trichlorvon converts to dichlorvos by metabolism in plants, as well as by biodegradation of the soil.

Trichlorfon/metrifonate was banned in New Zealand in 2011.[13]

Trichlorfon/metrifonate was banned in India from 2020.[14]

References

  1. ^ "Trichlorfon". Haz-Map. U.S. National Library of Medicine. August 2015. Retrieved 2015-10-13.
  2. ^ "Metrifonate". U.S. National Institute of Standards and Technology. Retrieved 2016-09-04.
  3. ^ "NLH - Neurological Conditions - Metrifonate for Alzheimer's disease". Archived from the original on 2009-07-19.
  4. ^ "Trichlorfon Facts". Pesticides: Reregistration. U.S. Environmental Protection Agency.
  5. ^ "Trichlorfon". R.E.D. Facts. U.S. Environmental Protection Agency.
  6. WHO. Archived from the original
    on June 3, 2016. Retrieved 2015-10-20. (dead link 31 January 2019)
  7. WHO. 1995. Archived from the original
    on July 15, 2010. Retrieved 2015-10-20.
  8. PMID 11961151
    .
  9. PMID 16625573
    .
  10. ^ "Reregistration Eligibility Decision Trichlorfon" (PDF). Retrieved 2018-08-09.
  11. ^ "Decision Guidance Document Trichlorfon - Rotterdam Convention" (PDF). Retrieved 2018-08-09.
  12. ^ "Argentina bans dichlorvos and trichlorfon". Retrieved 2018-08-09.
  13. ^ "New Zealand bans trichlorfon". Retrieved 2018-08-09.
  14. ^ "Banned Pesticides in India". 2018-01-17. Retrieved 2018-08-09.
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