Chemistry:Ambenonium chloride

Short description: Chemical compound

Ambenonium chloride

Clinical data
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a699058
Routes of administration	Oral
ATC code	N07AA30 (WHO)
Pharmacokinetic data
Bioavailability	Low
Identifiers
IUPAC name 2,2'-[(1,2-Dioxoethane-1,2-diyl)diimino]bis[N-(2-chlorobenzyl)-N,N-diethylethanaminium]
CAS Number	7648-98-8 Y
PubChem CID	8288
DrugBank	DB01122 N
ChemSpider	7987 Y
UNII	L16PUN799N
KEGG	D01001 Y
ChEBI	CHEBI:2628 Y
ChEMBL	ChEMBL1652 N
Chemical and physical data
Formula	C28H42Cl2N4O2+2
Molar mass	537.57 g·mol−1
3D model (JSmol)	Interactive image
SMILES [Cl-].[Cl-].Clc1ccccc1C[N+](CC)(CC)CCNC(=O)C(=O)NCC[N+](Cc2ccccc2Cl)(CC)CC
InChI InChI=1S/C28H40Cl2N4O2.2ClH/c1-5-33(6-2,21-23-13-9-11-15-25(23)29)19-17-31-27(35)28(36)32-18-20-34(7-3,8-4)22-24-14-10-12-16-26(24)30;;/h9-16H,5-8,17-22H2,1-4H3;2*1H Y Key:DXUUXWKFVDVHIK-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Ambenonium (as ambenonium dichloride, trade name Mytelase) is a cholinesterase inhibitor used in the management of myasthenia gravis.

It is classified as a reversible cholinesterase inhibitor.

Mechanism of action

Ambenonium exerts its actions against myasthenia gravis by competitive reversible inhibition of acetylcholinesterase, the enzyme responsible for the hydrolysis of acetylcholine. Myasthenia gravis occurs when the body produces antibodies against acetylcholine receptors, and thus inhibits signal transmission across the neuromuscular junction. Ambenonium reversibly binds acetylcholinesterase, inactivates it and therefore increases levels of acetylcholine. This, in turn, facilitates transmission of impulses across the myoneural junction and effectively treats the disease.

Indications

Ambenonium is used to treat muscle weakness due to disease or defect of the neuromuscular junction (myasthenia gravis).

Ambenonium was withdrawn from the market in the United States in 2010.