echothiophate iodide

ヨウ化エコチオパート、ヨウ化エコチオファート

関

echothiopate、echothiophate、ecothiopate、ecothiopate iodide

WordNet

1. a salt or ester of hydriodic acid

PrepTutorEJDIC

1. ヨウ化物

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/08/03 17:52:04」(JST)

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[Wiki en表示]

Echothiophate

Systematic (IUPAC) name
2-(Diethoxyphosphorylsulfanyl)ethyl-N,N,N-trimethylazanium iodide
Clinical data
Trade names	Phospholine
Pregnancy cat.	?
Legal status	?
Routes	Topical (eye drops)
Identifiers
CAS number	6736-03-4 Y
ATC code	S01EB03
PubChem	CID 10547
DrugBank	DB01057
ChemSpider	10107 Y
UNII	0F350BVT6S Y
KEGG	D02193 Y
ChEBI	CHEBI:59849 Y
ChEMBL	CHEMBL1201341 N
Chemical data
Formula	C9H23INO3PS
Mol. mass	383.228 g/mol
SMILES [I-].O=P(OCC)(OCC)SCC[N+](C)(C)C
InChI InChI=1S/C9H23NO3PS.HI/c1-6-12-14(11,13-7-2)15-9-8-10(3,4)5;/h6-9H2,1-5H3;1H/q+1;/p-1 Y Key:OVXQHPWHMXOFRD-UHFFFAOYSA-M Y
N (what is this?)  (verify)

Echothiophate (Phospholine) is a parasympathomimetic and a phosphorothioate. It is an irreversible acetylcholinesterase inhibitor.

Uses

It is used as an ocular antihypertensive in the treatment of chronic glaucoma and, in some cases, accommodative esotropia. It is available under several trade names such as Phospholine Iodide (Wyeth-Ayerst).

Echothiophate binds irreversibly to cholinesterase. Because of the very slow rate at which echothiophate is hydrolyzed by cholinesterase, its effects can last a week or more. Adverse effects include muscle spasm and other systemic effects.

Mechanism of action

It covalently binds by its phosphate group to serine group at the active site of the cholinesterase. Once bound, the enzyme is permanently inactive and the cell has to make new enzymes.

Shortage

Wyeth Pharmaceuticals stopped manufacturing echothiophate iodide in the US in 2003. After contacting the American Academy of Ophthalmology (AAO), Wyeth rescinded their decision and, according to AAO public relations representative Michelle Stephens, the AAO and Wyeth were in talks for about a year about manufacturing it.

In the meantime, a worldwide shortage of the drug has occurred.

Chemistry

Echothiophate is made by reacting diethylchlorophosphoric acid with 2-dimethylaminoethylmercaptan, giving S-(2-dimethylaminoethyl)-O,O-diethylthiophosphate, which is alkylated by methyl iodide, forming echothiophate.

References

UpToDate Contents

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• 1. 原発性乳児緑内障 primary infantile glaucoma
• 2. 有機リン剤およびカルバメート中毒 organophosphate and carbamate poisoning
• 3. 小児における水平斜視の原因 causes of horizontal strabismus in children

English Journal

• X-ray crystallographic snapshots of reaction intermediates in the G117H mutant of human butyrylcholinesterase, a nerve agent target engineered into a catalytic bioscavenger.

• Nachon F, Carletti E, Wandhammer M, Nicolet Y, Schopfer LM, Masson P, Lockridge O.SourceCellule Enzymologie, Departement de Toxicologie, Institut de Recherche Biomedicale des Armees-CRSSA, 24 avenue des Maquis du Gresivaudan, La Tronche, France. florian@nachon.net
• The Biochemical journal.Biochem J.2011 Jan 27;434(1):73-82.
• OPs (organophosphylates) exert their acute toxicity through inhibition of acetylcholinesterase, by phosphylation of the catalytic serine residue. Engineering of human butyrylcholinesterase, by substitution of a histidine residue for the glycine residue at position 117, led to the creation of OP hydr
• PMID 21091433

• Lowering of IOP by echothiophate iodide in pseudophakic eyes with glaucoma.

• Schmidt KG, Horowitz Y, Buckman G, Segev E, Levinger E, Geyer O.SourceGlaucoma Unit, Department of Ophthalmology, Starnberg, Germany.
• Current eye research.Curr Eye Res.2010 Aug;35(8):698-702.
• PMID 20673046

Japanese Journal

• 市販点眼薬の微生物汚染について

• 布施 昌孝,片倉 道啓,佐藤 百合子,吉田 義孝,照井 和幸,福島 豁行,鈴木 彰
• 病院薬学 4(2), 70-73, 1978-08-20
• … It was found that the following 3 ophthalmic solutions were contaminated with Candida Krusei, Escherichia coli, Staphylococcus epidermidis and Gaffkya tetragena : Catalin, phospholine Iodide (Echothiophate Iodide) and Artificial Tear. …
• NAID 110001797913

Related Links

• Echothiophate - Wikipedia, the free encyclopedia

Wyeth Pharmaceuticals stopped manufacturing echothiophate iodide in the US in 2003. After contacting the American Academy of Ophthalmology (AAO), Wyeth rescinded their decision and, according to AAO public relations representative ...

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★リンクテーブル★

リンク元	「エコチオパート」「ヨウ化エコチオパート」「ecothiopate iodide」「ecothiopate」「echothiopate」
関連記事	「echothiophate」「iodide」

「エコチオパート」

　　[★]

英

echothiophate、((欧州))ecothiopate、echothiopate、echothiophate iodide、ecothiopate iodide

関

エコチオファート、ヨウ化エコチオファート、ヨウ化エコチオパート

「ヨウ化エコチオパート」

　　[★]

英

echothiophate iodide、ecothiopate iodide

関

エコチオパート、ヨウ化エコチオファート

「ecothiopate iodide」

　　[★]

ヨウ化エコチオパート

関

echothiopate、echothiophate、echothiophate iodide、ecothiopate

「ecothiopate」

　　[★]

エコチオパート

関

echothiopate、echothiophate、echothiophate iodide、ecothiopate iodide

「echothiopate」

　　[★]

• エコチオパート

関

echothiophate、echothiophate iodide、ecothiopate、ecothiopate iodide

「echothiophate」

　　[★]

エコチオパート、エコチオファート

関

echothiopate、echothiophate iodide、ecothiopate、ecothiopate iodide

「iodide」

　　[★]

• n.

• ヨウ化物、ヨウ化

• adj.

• ヨウ素の

関

I、I2、iodine、iodo