Ambenonium chloride

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 ;
PubChem CID	8288;
DrugBank	DB01122 ;
ChemSpider	7987 ;
UNII	L16PUN799N;
KEGG	D01001 ;
ChEBI	CHEBI:2628 ;
ChEMBL	ChEMBL1652 ;
CompTox Dashboard (EPA)	DTXSID5048396 ;
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 ; Key:DXUUXWKFVDVHIK-UHFFFAOYSA-N ;
	(what is this?) (verify)

Ambenonium (as ambenonium dichloride, trade name Mytelase) is a cholinesterase inhibitor[1] used in the management of myasthenia gravis.

It is classified as reversible.[2]

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 myoneural 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Ambenonium was withdrawn from the market in the United States in 2010.[3]

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References

Bolognesi ML, Cavalli A, Andrisano V, et al. (September 2003). "Design, synthesis and biological evaluation of ambenonium derivatives as AChE inhibitors". Farmaco. 58 (9): 917–28. doi:10.1016/S0014-827X(03)00150-2. PMID 13679187.
Hodge AS, Humphrey DR, Rosenberry TL (May 1992). "Ambenonium is a rapidly reversible noncovalent inhibitor of acetylcholinesterase, with one of the highest known affinities". Mol. Pharmacol. 41 (5): 937–42. PMID 1588924.
"Ambenonium". St. Elizabeth Healthcare. Archived from the original on 2015-09-08. Retrieved 2016-02-10.

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[pmid13679187-1] Bolognesi ML, Cavalli A, Andrisano V, et al. (September 2003). "Design, synthesis and biological evaluation of ambenonium derivatives as AChE inhibitors". Farmaco. 58 (9): 917–28. doi:10.1016/S0014-827X(03)00150-2. PMID 13679187.

[pmid1588924-2] Hodge AS, Humphrey DR, Rosenberry TL (May 1992). "Ambenonium is a rapidly reversible noncovalent inhibitor of acetylcholinesterase, with one of the highest known affinities". Mol. Pharmacol. 41 (5): 937–42. PMID 1588924.

[3] "Ambenonium". St. Elizabeth Healthcare. Archived from the original on 2015-09-08. Retrieved 2016-02-10.