トリクロルホン
- 関
- metrifonate
- 関
- Metrifonate
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/12/06 16:44:26」(JST)
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Metrifonate
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Systematic (IUPAC) name |
(RS)-Dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate |
Clinical data |
AHFS/Drugs.com |
International Drug Names |
Legal status |
?
|
Pharmacokinetic data |
Half-life |
3 hours |
Identifiers |
CAS number |
52-68-6 Y |
ATC code |
P02BB01 QP52AB01 QP53AF02 |
PubChem |
CID 5853 |
ChemSpider |
5644 |
UNII |
DBF2DG4G2K Y |
KEGG |
C07971 Y |
ChEBI |
CHEBI:6908 Y |
Synonyms |
Trichlorphon |
Chemical data |
Formula |
C4H8Cl3O4P |
Mol. mass |
257.436 g/mol |
SMILES
- COP(=O)(C(C(Cl)(Cl)Cl)O)OC InChI = 1/C4H8Cl3O4P/c1-10-12(9,11-2)3(8)4(5,6)7/h3,8H,1-2H3
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InChI
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InChI=1S/C4H8Cl3O4P/c1-10-12(9,11-2)3(8)4(5,6)7/h3,8H,1-2H3
Key:NFACJZMKEDPNKN-UHFFFAOYSA-N
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Y (what is this?) (verify) |
Metrifonate (INN) or trichlorfon (USAN) is an irreversible organophosphate acetylcholinesterase inhibitor.[1] It is a prodrug which is activated non-enzymatically into 2,2-dichlorovinyl dimethyl phosphate (DDVP).
It is used as an insecticide.
It can be used to treat schistosomiasis caused by Schistoma haematobium but is no longer commercially available.[2]
It has been proposed for use in treatment of Alzheimer's disease, but use for that purpose is not currently recommended.[3]
References
- ^ "NLH - Neurological Conditions - Metrifonate for Alzheimer's disease".
- ^ Ross A.G.P., Bartley P.B., Sleigh A.C., Olds G.R., Li Y., Williams G.M., and McManus D.P. (2002). "Schistosomiasis". The New England Journal of Medicine 346 (16): 1212–1220. doi:10.1056/NEJMra012396. PMID 11961151.
- ^ López-Arrieta J, Schneider L (2008). López-Arrieta, Jess, ed. "Metrifonate for Alzheimer's disease". Cochrane Database of Systematic Reviews (1): CD003155. doi:10.1002/14651858.CD003155.pub3. PMID 16625573.
Antiparasitics – Anthelmintics (P02) and Endectocides (QP54)
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Antiplatyhelmintic agents |
Antitrematodals
(schistosomicides)
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Binds tubulin
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AI
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Other/unknown
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- quinoline
- Praziquantel#
- Oxamniquine#
- phenol
- thiazole
- arylsulfonate
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Anticestodals
(taeniacides)
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Binds tubulin
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Other/unknown
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- salicylanilide
- aminoacridine
- butyrophenone
- chlorophenol
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Antinematodal agents
(including
macrofilaricides) |
Binds tubulin
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- benzimidazole
- Mebendazole#
- Albendazole#
- Thiabendazole
- Fenbendazole
- Ciclobendazole
- Flubendazole
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Glutamate-gated chloride channel, GABA receptor
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- avermectins
- Abamectin
- Doramectin
- Emamectin
- Ivermectin
- Selamectin
- milbemycins
- Moxidectin
- Milbemycin oxime
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NMDA
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- tetrahydropyrimidine
- Pyrantel#
- Pyrantel pamoate
- Oxantel
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Other/unknown
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- piperazine
- Piperazine
- Diethylcarbamazine#
- thiazole
- quinolinium
- benzylammonium
- naphthalenesulfonate
- Tribendimidine
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Psychoanaleptics: Antidementia agents (N06D)
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Anticholinesterases |
- Cymserine
- Donepezil
- Galantamine
- Huperzine A (Huperzia serrata)
- Ladostigil
- Rivastigmine
- Stemazole
- Tacrine
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Others |
- Bifemelane
- Bilobalide (Ginkgo biloba)
- Cerlapirdine
- Ensaculin
- Latrepirdine
- Lecozotan
- Leteprinim
- Memantine
- Semagacestat
- Ergoloid
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dsrd (o, p, m, p, a, d, s), sysi/epon, spvo
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proc (eval/thrp), drug (N5A/5B/5C/6A/6B/6D)
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Cholinergics
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Receptor ligands
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mACh
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- Agonists: 77-LH-28-1
- AC-42
- AC-260,584
- Aceclidine
- Acetylcholine
- AF30
- AF150(S)
- AF267B
- AFDX-384
- Alvameline
- AQRA-741
- Arecoline
- Bethanechol
- Butyrylcholine
- Carbachol
- CDD-0034
- CDD-0078
- CDD-0097
- CDD-0098
- CDD-0102
- Cevimeline
- Choline
- cis-Dioxolane
- Ethoxysebacylcholine
- Itameline
- LY-593,039
- L-689,660
- LY-2,033,298
- McNA343
- Methacholine
- Milameline
- Muscarine
- NGX-267
- Ocvimeline
- Oxotremorine
- PD-151,832
- Pilocarpine
- RS86
- Sabcomeline
- SDZ 210-086
- Sebacylcholine
- Suberyldicholine
- Talsaclidine
- Tazomeline
- Thiopilocarpine
- Vedaclidine
- VU-0029767
- VU-0090157
- VU-0152099
- VU-0152100
- VU-0238429
- WAY-132,983
- Xanomeline
- YM-796
- Antagonists: 3-Quinuclidinyl benzilate
- 4-DAMP
- Aclidinium bromide
- Anisodamine
- Anisodine
- Atropine
- Atropine methonitrate
- Benactyzine
- Benzatropine (benztropine)
- Benzydamine
- BIBN 99
- Biperiden
- Bornaprine
- CAR-226,086
- CAR-301,060
- CAR-302,196
- CAR-302,282
- CAR-302,368
- CAR-302,537
- CAR-302,668
- CS-27349
- Cyclobenzaprine
- Cyclopentolate
- Darifenacin
- DAU-5884
- Dimethindene
- Dexetimide
- DIBD
- Dicyclomine (dicycloverine)
- Ditran
- EA-3167
- EA-3443
- EA-3580
- EA-3834
- Etanautine
- Etybenzatropine (ethybenztropine)
- Flavoxate
- Himbacine
- HL-031,120
- Ipratropium bromide
- J-104,129
- Hyoscyamine
- Mamba toxin 3
- Mamba toxin 7
- Mazaticol
- Mebeverine
- Methoctramine
- Metixene
- N-Ethyl-3-piperidyl benzilate
- N-Methyl-3-piperidyl benzilate
- Orphenadrine
- Otenzepad
- Oxybutynin
- PBID
- PD-102,807
- PD-0298029
- Phenglutarimide
- Phenyltoloxamine
- Pirenzepine
- Piroheptine
- Procyclidine
- Profenamine
- RU-47,213
- SCH-57,790
- SCH-72,788
- SCH-217,443
- Scopolamine (hyoscine)
- Solifenacin
- Telenzepine
- Tiotropium bromide
- Tolterodine
- Trihexyphenidyl
- Tripitamine
- Tropatepine
- Tropicamide
- WIN-2299
- Xanomeline
- Zamifenacin; Others: 1st generation antihistamines (e.g., brompheniramine
- chlorphenamine
- cyproheptadine
- dimenhydrinate
- diphenhydramine
- doxylamine
- mepyramine (pyrilamine)
- phenindamine
- pheniramine
- tripelennamine
- triprolidine)
- Tricyclic antidepressants (e.g., imipramine, amitriptyline)
- Tetracyclic antidepressants (e.g., amoxapine, maprotiline)
- Typical antipsychotics (e.g., chlorpromazine, thioridazine)
- Atypical antipsychotics (e.g., clozapine, olanzapine)
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nACh
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- Agonists: 5-HIAA
- A-84,543
- A-366,833
- A-582,941
- A-867,744
- ABT-202
- ABT-418
- ABT-560
- ABT-894
- Acetylcholine
- Altinicline
- Anabasine
- Anatoxin-a
- AR-R17779
- Butinoline
- Butyrylcholine
- Carbachol
- Choline
- Cotinine
- Cytisine
- Decamethonium
- Desformylflustrabromine
- Dianicline
- Dimethylphenylpiperazinium
- Epibatidine
- Epiboxidine
- Ethanol
- Ethoxysebacylcholine
- EVP-4473
- EVP-6124
- Galantamine
- GTS-21
- Ispronicline
- Levamisole
- Lobeline
- MEM-63,908 (RG-3487)
- Morantel
- Nicotine (tobacco)
- NS-1738
- PHA-543,613
- PHA-709,829
- PNU-120,596
- PNU-282,987
- Pozanicline
- Rivanicline
- RJR-2429
- Sazetidine A
- Sebacylcholine
- SIB-1508Y
- SIB-1553A
- SSR-180,711
- Suberyldicholine
- Suxamethonium (succinylcholine)
- TC-1698
- TC-1734
- TC-1827
- TC-2216
- TC-5214
- TC-5619
- TC-6683
- Tebanicline
- Tropisetron
- UB-165
- Varenicline
- WAY-317,538
- XY-4083
- Antagonists: 18-MAC
- 18-MC
- α-Bungarotoxin
- α-Conotoxin
- Alcuronium
- Allopregnanolone
- Amantadine
- Anatruxonium
- Atracurium
- Bupropion
- Chandonium
- Chlorisondamine
- Cisatracurium
- Coclaurine
- Coronaridine
- Cyclopropane
- Dacuronium
- Decamethonium
- Desflurane
- Dextromethorphan
- Dextropropoxyphene
- Dextrorphan
- Diadonium
- DHβE
- Dihydrochandonium
- Dimethyltubocurarine (metocurine)
- Dipyrandium
- Dizocilpine (MK-801)
- Doxacurium
- Enflurane
- Esketamine
- Fazadinium
- Gallamine
- Halothane
- Hexafluronium
- Hexamethonium (benzohexonium)
- Hydroxybupropion
- Ibogaine
- Isoflurane
- Ketamine
- Kynurenic acid
- Laudexium (laudolissin)
- Levacetylmethadol
- Levomethadone
- Malouetine
- ME-18-MC
- Mecamylamine
- Memantine
- Methadone
- Methorphan (racemethorphan)
- Methyllycaconitine
- Metocurine
- Mivacurium
- Morphanol (racemorphan)
- Neramexane
- Nitrous oxide
- Pancuronium bromide
- Pempidine
- Pentamine
- Pentolinium
- Phencyclidine
- Pipecuronium
- Progesterone
- Radafaxine
- Rapacuronium
- Rocuronium
- Sevoflurane
- Surugatoxin
- Thiocolchicoside
- Toxiferine
- Tramadol
- Trimetaphan camsilate (trimethaphan camsylate)
- Tropeinium
- Tubocurarine
- Vanoxerine
- Vecuronium
- Xenon
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Reuptake inhibitors
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CHT
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- Hemicholinium-3 (hemicholine)
- Triethylcholine
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VAChT
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Enzyme inhibitors
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ChAT
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- 1-(-Benzoylethyl)pyridinium
- 2-(α-Naphthoyl)ethyltrimethylammonium
- 3-Chloro-4-stillbazole
- 4-(1-Naphthylvinyl)pyridine
- Acetylseco hemicholinium-3
- Acryloylcholine
- AF64A
- B115
- BETA
- CM-54,903
- N,N-Dimethylaminoethylacrylate
- N,N-Dimethylaminoethylchloroacetate
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AChE
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BChE
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Note: Many of the AChE inhibitors listed above also act as BChE inhibitors.
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Others
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Precursors
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- Choline (lecithin)
- Citicoline
- Cyprodenate
- Dimethylethanolamine
- Glycerophosphocholine
- Meclofenoxate (centrophenoxine)
- Phosphatidylcholine
- Phosphatidylethanolamine
- Phosphorylcholine
- Pirisudanol
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Cofactors
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- Acetic acid
- Acetylcarnitine
- Acetyl-coA
- Vitamin B5
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Others
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- Acetylcholine releasing agents: α-Latrotoxin
- β-Bungarotoxin; Acetylcholine release inhibitors: Botulinum toxin (Botox); Acetylcholinesterase reactivators: Asoxime
- Obidoxime
- Pralidoxime
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English Journal
- Development of direct competitive biomimetic immunosorbent assay based on quantum dot label for determination of trichlorfon residues in vegetables.
- Liu Q1, Jiang M1, Ju Z2, Qiao X3, Xu Z4.
- Food chemistry.Food Chem.2018 Jun 1;250:134-139. doi: 10.1016/j.foodchem.2017.12.079. Epub 2018 Jan 3.
- PMID 29412902
- Monogenean parasites infect ornamental fish imported to Australia.
- Trujillo-González A1, Becker JA2, Vaughan DB3, Hutson KS3.
- Parasitology research.Parasitol Res.2018 Feb 9. doi: 10.1007/s00436-018-5776-z. [Epub ahead of print]
- PMID 29427156
- Transcriptome analysis of Rana chensinensis liver under trichlorfon stress.
- Ma Y1, Li B1, Ke Y2, Zhang Y3, Zhang Y4.
- Ecotoxicology and environmental safety.Ecotoxicol Environ Saf.2018 Jan;147:487-493. doi: 10.1016/j.ecoenv.2017.09.016. Epub 2017 Sep 14.
- PMID 28910747
Japanese Journal
- Delayed Polyneuropathy Induced by Organophosphate Poisoning
- Kobayashi Shunsuke,Okubo Reiko,Ugawa Yoshikazu
- Internal Medicine 56(14), 1903-1905, 2017
- … <p>An 89-year-old man attempted suicide by ingesting a pesticide (trichlorfon). …
- NAID 130005773818
- 等脚類Caecognathia coralliophilaに対するホルマリン,トリクロルホン,過酸化水素および硫酸銅の抗寄生虫効果(英文)
- Thing Chong Yen,Ransangan Julian,Hatai Kishio
- 魚病研究 51(3), 125-127, 2016
- … The effects of copper sulfate, formalin, trichlorfon, and hydrogen peroxide on the survival of <i>C. … Trichlorfon was found to be the most effective, killing the parasites within 24 h at 0.2 ppm. … Consequently, the toxicity of trichlorfon to tiger grouper was tested. … Fish were exposed to trichlorfon at 0.2 ppm for 24 h or 3.2 ppm for 60 min. No fish died in the experiment. …
- NAID 130005420466
- 国内の養鶏場におけるワクモ<i>Dermanyssus gallinae</i>の市販殺虫剤に対する抵抗性出現
- 村野 多可子,並木 一男,椎名 幸一 [他],安川 久
- 日本獣医師会雑誌 68(8), 509-514, 2015
- ワクモの駆除を目的とした市販のカーバメイト系製剤3剤,ピレスロイド系製剤1剤,有機リン系製剤3剤,ハエの駆除を目的とした市販のピレスロイド系製剤2剤,ピレスロイド系と有機リン系の合剤2製剤を用いて,2007~2013年の7年間ワクモの薬剤抵抗性出現について調査した.7年間の調査結果は2007~2010年の4年間と2011~2013年の3年間に分けて集計した.前半の4年間は1道1府30県139農場, …
- NAID 130005099528
Related Links
- 環境保健クライテリア 132 Environmental Health Criteria 132 トリクロルホン Trichlorfon (原著162頁,1992年発行) ... 1.物質の同定、物理的・化学的特性、分析方法 a 物質の同定 化学式 C4H8Cl3O4P 化学構造 3次元の ...
- the message 英語マスターの鍵である冠詞についてみていきましょう。今日の会話はLucyが先週田中さんに送付したプロ 解説を読む
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