edrophonium (CHEBI:251408)

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ChEBI Name	edrophonium

ChEBI ID	CHEBI:251408

Definition	A quaternary ammonium ion that is N-ethyl-N,N-dimethylanilinium in which one of the meta positions is substituted by a hydroxy group. It is a reversible inhibitor of cholinesterase, with a rapid onset (30-60 seconds after injection) but a short duration of action (5-15 minutes). The chloride salt is used in myasthenia gravis both diagnostically and to distinguish between under- or over-treatment with other anticholinesterases. It has also been used for the reversal of neuromuscular blockade in anaesthesia, and for the management of poisoning due to tetrodotoxin, a neuromuscular blocking toxin found in puffer fish and other marine animals.

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

Secondary ChEBI IDs	CHEBI:42376, CHEBI:4758

Supplier Information

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Formula

C10H16NO

Net Charge

Average Mass

166.24010

Monoisotopic Mass

166.12264

InChI

InChI=1S/C10H15NO/c1-4-11(2,3)9-6-5-7-10(12)8-9/h5-8H,4H2,1-3H3/p+1

InChIKey

VWLHWLSRQJQWRG-UHFFFAOYSA-O

SMILES

CC[N+](C)(C)c1cccc(O)c1

Roles Classification
Biological Role(s):	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):	diagnostic agent A substance administered to aid diagnosis of a disease. antidote Any protective agent counteracting or neutralizing the action of poisons.

ChEBI Ontology
Outgoing	edrophonium (CHEBI:251408) has role antidote (CHEBI:50247) edrophonium (CHEBI:251408) has role diagnostic agent (CHEBI:33295) edrophonium (CHEBI:251408) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733) edrophonium (CHEBI:251408) is a phenols (CHEBI:33853) edrophonium (CHEBI:251408) is a quaternary ammonium ion (CHEBI:35267)

Incoming	edrophonium chloride (CHEBI:4759) has part edrophonium (CHEBI:251408)

IUPAC Name

N-ethyl-3-hydroxy-N,N-dimethylanilinium

Synonyms	Sources
(3-hydroxyphenyl)dimethylethylammonium	ChEBI
3-hydroxy-N,N-dimethyl-N-ethylanilinium	ChEBI
Edrophonium	KEGG COMPOUND
EDROPHONIUM	ChEMBL
edrophonium	ChEMBL
EDROPHONIUM ION	PDBeChem
Ethyl-(3-hydroxy-phenyl)-dimethyl-ammonium	ChEMBL
N-ethyl-3-hydroxy-N,N-dimethylbenzenaminium	ChEBI

Citation	Type	Source
7488499	PubMed citation	Europe PMC

Last Modified

20 August 2018