Ambenonium chloride - Misplaced Pages

Chemical compound Pharmaceutical 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'-bis
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
Molar mass	537.57 g·mol
3D model (JSmol)	Interactive image
SMILES ..Clc1ccccc1C(CC)(CC)CCNC(=O)C(=O)NCC(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
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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Ambenonium was withdrawn from the market in the United States in 2010.

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.