ecothiopate (CHEBI:4753)

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ChEBI Name	ecothiopate

ChEBI ID	CHEBI:4753

Definition	The phosphorothioate obtained by formal condensation of diethyl phosphate with N,N,N-trimethyl-2-sulfanylethanaminium. An irreversible acetylcholinesterase inhibitor, its iodide salt is used an ocular antihypertensive in the treatment of open-angle glaucoma, particularly when other drugs have proved inadequate.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C9H23NO3PS

Net Charge

Average Mass

256.32300

Monoisotopic Mass

256.11308

InChI

InChI=1S/C9H23NO3PS/c1-6-12-14(11,13-7-2)15-9-8-10(3,4)5/h6-9H2,1-5H3/q+1

InChIKey

BJOLKYGKSZKIGU-UHFFFAOYSA-N

SMILES

CCOP(=O)(OCC)SCC[N+](C)(C)C

Roles Classification
Biological Role(s):	miotic An agent causing contraction of the pupil of the eye. Because the size of the pupil is under the antagonistic control of the sympathetic and parasympathetic systems, drugs affecting either system can cause miosis. Drugs that mimic or potentiate the parasympathetic input to the circular constrictor muscle and drugs that inhibit sympathetic input to the radial dilator muscle tend to contract the pupils. EC 3.1.1.8 (cholinesterase) inhibitor An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).

Application(s):	miotic An agent causing contraction of the pupil of the eye. Because the size of the pupil is under the antagonistic control of the sympathetic and parasympathetic systems, drugs affecting either system can cause miosis. Drugs that mimic or potentiate the parasympathetic input to the circular constrictor muscle and drugs that inhibit sympathetic input to the radial dilator muscle tend to contract the pupils.

ChEBI Ontology
Outgoing	ecothiopate (CHEBI:4753) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733) ecothiopate (CHEBI:4753) has role miotic (CHEBI:51068) ecothiopate (CHEBI:4753) is a organic thiophosphate (CHEBI:37512) ecothiopate (CHEBI:4753) is a phosphocholines (CHEBI:36700) ecothiopate (CHEBI:4753) is a quaternary ammonium ion (CHEBI:35267)

Incoming	ecothiopate iodide (CHEBI:59849) has part ecothiopate (CHEBI:4753)

IUPAC Name

2-[(diethoxyphosphoryl)sulfanyl]-N,N,N-trimethylethanaminium

Synonyms	Sources
(2-diethoxyphosphinylthioethyl)trimethylammonium	ChEBI
Echothiophate	KEGG COMPOUND

Last Modified

22 February 2017