(2R)-N-benzyl-2-acetamido-3-methoxypropanamide

• ChemBase ID: 72595
• Molecular Formular: C13H18N2O3
• Molecular Mass: 250.29362
• Monoisotopic Mass: 250.13174245
• SMILES: C(=O)([C@@H](COC)NC(=O)C)NCc1ccccc1
• Canonical 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
• InChIKey: VPPJLAIAVCUEMN-GFCCVEGCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-N-benzyl-2-acetamido-3-methoxypropanamide
• IUPAC Traditional name: lacosamide
• Synonyms: (2R)-N-benzyl-2-acetamido-3-methoxypropanamide; (R)-2-Acetamido-N-benzyl-3-methoxypropanamide; Erlosamide; Vimpat; Lacosamide

Database IDs

• CAS Number: 175481-36-4
• MDL Number: MFCD08272557
• PubChem SID: 162037520
• PubChem CID: 219078

CALCULATED PROPERTIES

• Acid pKa: 12.468967
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.022441661
• LogD (pH = 7.4): -0.022444889
• Log P: -0.022441605
• Molar Refractivity: 67.5675 cm^3
• Polarizability: 26.340395 Å^3
• Polar Surface Area: 67.43 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Hydrophobicity(logP): 0.392

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Target: Sodium channel

Product Information

• Purity: 95%; 95+%
• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1253

Research Area: Epilepsy, Fibromyalgia
Biological Activity:
Lacosamide is a medication developed for the adjunctive treatment of partial-onset seizures and diabetic neuropathic pain. [1]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, it enhances slow inactivation.[1]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. [1]

REFERENCES

• http://en.wikipedia.org/wiki/Lacosamide