lacosamide   Click here for help

GtoPdb Ligand ID: 7472

Synonyms: ADD 234037 | erlosamide | harkeroside | SPM 927 | Vimpat®
Approved drug
lacosamide is an approved drug (EMA and FDA (2008))
Compound class: Synthetic organic
Comment: Lacosamide is a functionalized amino acid anticonvulsant drug [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 67.43
Molecular weight 250.13
XLogP 0.51
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COCC(C(=O)NCc1ccccc1)NC(=O)C
Isomeric SMILES COC[C@H](C(=O)NCc1ccccc1)NC(=O)C
InChI InChI=1S/C13H18N2O3/c1-10(16)15-12(9-18-2)13(17)14-8-11-6-4-3-5-7-11/h3-7,12H,8-9H2,1-2H3,(H,14,17)(H,15,16)/t12-/m1/s1
InChI Key VPPJLAIAVCUEMN-GFCCVEGCSA-N
References
1. Abdelsayed M, Sokolov S, Ruben PC. (2013)
A thermosensitive mutation alters the effects of lacosamide on slow inactivation in neuronal voltage-gated sodium channels, NaV1.2.
Front Pharmacol, 4: 121. [PMID:24065921]
2. Beyreuther BK, Freitag J, Heers C, Krebsfänger N, Scharfenecker U, Stöhr T. (2007)
Lacosamide: a review of preclinical properties.
CNS Drug Rev, 13 (1): 21-42. [PMID:17461888]
3. Sheets PL, Heers C, Stoehr T, Cummins TR. (2008)
Differential block of sensory neuronal voltage-gated sodium channels by lacosamide [(2R)-2-(acetylamino)-N-benzyl-3-methoxypropanamide], lidocaine, and carbamazepine.
J. Pharmacol. Exp. Ther., 326 (1): 89-99. [PMID:18378801]