ChemicalBook CAS DataBase List 52022-31-8

52022-31-8

Name	AMBENONIUM DICHLORIDE
CAS	52022-31-8
Molecular Formula	C28H42Cl4N4O2
MDL Number	MFCD00153762
Molecular Weight	608.47
MOL File	52022-31-8.mol

Chemical Properties

storage temp.

Store at RT

Hazard Information

Uses

Ambenonium (WIN 8077) dichloride tetrahydrate is an orally active and reversible inhibitor of Acetyicholinesterase (AChE) with high affinity. Ambenonium dichloride tetrahydrate inhibits human AChE with an IC50 value of 0.7 nM (hAChE)[1][2].

Biological Activity

Extremely potent, selective and rapidly reversible inhibitor of acetylcholinesterase (AChE) (IC 50 values are 0.000698 and 8.20 μ M at AChE and BChE respectively).

in vivo

Ambenonium dichloride tetrahydrate (6 mg/kg; p.o.; daily; 30-60 d) results an adverse effect on neuromuscular transmission in long-term administration, and induces hypersensitivity to stimulation in myasthenia gravis mice modle^[3].
Ambenonium dichloride tetrahydrate (6 mg/kg; p.o.; daily; 14 d) decreases the number of AChR in motorend-plates^[3].

Animal Model:	Female Sprague Dawley rats (weight 250 g) with myasthenia gravis^[3]
Dosage:	6 mg/kg
Administration:	Oral gavage; daily; 14, 30, 60, 90, 360 days (Stop administration 24 h in advance)
Result:	Resulted general activity decreasing and hypersensity to stimulation in rats during day 30-60, but these behaviors disappeared on day 90. Induced degeneration and simplification of the postsynaptic folds, widening of the synaptic clefts, increased number of the postsynaptic vesicles, and reduction in the number of the AChR in the postsynaptic membrane on day 360.

References

[1] Hodge AS, et al. Ambenonium is a rapidly reversible noncovalent inhibitor of acetylcholinesterase, with one of the highest known affinities. Mol Pharmacol. 1992 May. 41(5):937-42. PMID:1588924
[2] Komloova M, et al. Preparation, in vitro screening and molecular modelling of symmetrical bis-quinolinium cholinesterase inhibitors--implications for early myasthenia gravis treatment. Bioorg Med Chem Lett. 2011 Apr 15. 21(8):2505-9. DOI:10.1016/j.bmcl.2011.02.047
[3] Hazama R, et al. Effects of long-term administration of ambenonium chloride on motor end-plate fine structure and acetylcholine receptor in rat. J Neurol Sci. 1981 Jul. 51(1):69-79. DOI:10.1016/0022-510x(81)90060-5

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