Edrophonium

Edrophonium

Systematic (IUPAC) name
N-ethyl-3-hydroxy-N,N-dimethylbenzenaminium
Clinical data
Trade names	Tensilon
AHFS/Drugs.com	FDA Professional Drug Information
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	116-38-1
ATC code	None
PubChem	CID 8307
DrugBank	APRD00944
ChemSpider	8006 Y
UNII	QO611KSM5P Y
KEGG	D00994 Y
ChEBI	CHEBI:4759 Y
ChEMBL	CHEMBL1128 Y
Chemical data
Formula	C10H16NO+
Mol. mass	166.24 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C10H15NO.ClH/c1-4-11(2,3)9-6-5-7-10(12)8-9;/h5-8H,4H2,1-3H3;1H Y Key:BXKDSDJJOVIHMX-UHFFFAOYSA-N Y
Y (what is this?)  (verify)

Edrophonium is a readily reversible acetylcholinesterase inhibitor. It prevents breakdown of the neurotransmitter acetylcholine and acts by competitively inhibiting the enzyme acetylcholinesterase, mainly at the neuromuscular junction. It is sold under the trade names Tensilon, Enlon and Reversol.

Clinical uses

Indication: edrophonium (by the so-called Tensilon test) is used to differentiate myasthenia gravis from cholinergic crisis. In myasthenia gravis, where a person is not able to produce enough neuromuscular stimulation, edrophonium will reduce the muscle weakness by effectively supplying more acetylcholine. In a cholinergic crisis, where a person has too much neuromuscular stimulation, edrophonium will make the muscle weakness worse by inducing a depolarizing block.

Chemistry

Edrophonium, ethyl-(3-hydroxyphenyl)dimethylammonium chloride, is made by reacting 3-dimethylaminophenol with ethyl bromide, which forms ethyl(3-hydroxyphenyl)dimethylammonium bromide, the bromine atom of which is replaced with a chlorine atom by reacting it with silver chloride, giving edrophonium.

• J.A. Aeschlimann, A. Stempel, U.S. Patent 2,647,924 (1953).

Sources

1. Brenner, G. M. (2000). Pharmacology. Philadelphia, PA: W.B. Saunders Company. ISBN 0-7216-7757-6
2. Canadian Pharmacists Association (2000). Compendium of Pharmaceuticals and Specialties (25th ed.). Toronto, ON: Webcom. ISBN 0-919115-76-4