V0815 Lacosamide - AK Scientific
 
 
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  Catalog ID # V0815
Lacosamide
, 98%
 
(2R)-2-(Acetylamino)-N-benzyl-3-methoxypropanamide




IDENTITY
CAS Registry #:[175481-36-4]
MDL Number:MFCD08272557
MF:C13H18N2O3
MW:250.29
SPECIFICATIONS & PROPERTIES
Purity:98%
Physical Form:White to off-white powder
Melting Point:141-146°C
Optical Rotation:+16° (c=1, MeOH)
Long-Term Storage:Store at 2-8°C
Shipping:Normal Temperature

BIOLOGICAL INFO
Application(s):A medication developed for the adjunctive treatment of partial-onset seizures and diabetic neuropathic pain

REVIEW

 Lacosamide is a functionalized amino acid that has activity in the maximal electroshock seizure test, like antiepileptic drugs that are believed to act through voltage-gated sodium channels. However, lacosamide does not act in a conventional way to stabilize fast sodium channel inactivation. Rather, recent studies indicate that it enhances slow inactivation. During an action potential, voltage-gated sodium channels undergo fast inactivation. This inactivation prevents the channel from opening, and helps end the action potential. Many antiepileptic drugs, like carbamazepine or lamotrigine, slow the recovery from inactivation and hence reduce the ability of neurons to fire action potentials. Inactivation only occurs in neurons firing action potentials; this means that drugs that modulate fast inactivation selectively reduce the firing in active cells. Slow inactivation is similar but does not produce complete blockade of voltage gated sodium channels, with both activation and inactivation occurring over hundreds of milliseconds or more. Lacosamide makes this inactivation happen at less depolarized membrane potentials. This means that lacosamide only affects neurons which are depolarized or active for long periods of time, typical of neurons at the focus of an epileptic focus. Lacosamide does not affect AMPA, kainate, NMDA, GABAA, GABAB or a variety of dopaminergic, serotonergic, adrenergic, muscarinic or cannabinoid receptors and does not block potassium or calcium currents.

REFERENCES
[1]Rogawski MA (June 2006). ""Diverse mechanisms of antiepileptic drugs in the development pipeline"". Epilepsy Res. 69 (3): 273-94. doi:10.1016/j.eplepsyres.2006.02.004. PMC 1562526. PMID 16621450.
[2] Errington AC, St?hr T, Heers C, Lees G (January 2008). "The investigational anticonvulsant lacosamide selectively enhances slow inactivation of voltage-gated sodium channels". Molecular Pharmacology 73 (1): 157-69. doi:10.1124/mol.107.039867. PMID 17940193.
[3] Errington AC, Coyne L, St?hr T, Selve N, Lees G (June 2006). "Seeking a mechanism of action for the novel anticonvulsant lacosamide". Neuropharmacology 50 (8): 1016-29. doi:10.1016/j.neuropharm.2006.02.002. PMID 16620882.

Risk Description(s)
R36/37/38:Irritating to eyes, respiratory system and skin

Safety Description(s)
S24/25:Avoid contact with skin and eyes.


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CATEGORIES

 APIs and Bioactives > Anticonvulsants

USEFUL LINKS

  PubChem