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Lacosamide

Base Information Edit
  • Chemical Name:Lacosamide
  • CAS No.:175481-36-4
  • Molecular Formula:C13H18N2O3
  • Molecular Weight:250.298
  • Hs Code.:2924296000
  • European Community (EC) Number:700-539-8,605-756-0
  • UNII:563KS2PQY5
  • DSSTox Substance ID:DTXSID1057666
  • Nikkaji Number:J1.029.117H
  • Wikipedia:Lacosamide
  • Wikidata:Q420077
  • NCI Thesaurus Code:C83859
  • RXCUI:623400
  • Pharos Ligand ID:UQNT2XADN7BW
  • Metabolomics Workbench ID:149687
  • ChEMBL ID:CHEMBL58323
  • Mol file:175481-36-4.mol
Lacosamide

Synonyms:lacosamide;N benzyl 2 acetamido 3 methoxypropionamide;N benzyl AcMeOPrNH2;N-benzyl-2-acetamido-3-methoxypropionamide;N-benzyl-AcMeOPrNH2;vimpat

Suppliers and Price of Lacosamide
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • Sigma-Aldrich
  • Lacosamide solution 1.0?mg/mL in acetonitrile, ampule of 1?mL, certified reference material, Cerilliant?
  • 1 mL
  • $ 159.00
  • Sigma-Aldrich
  • Lacosamide solution 1.0mg/mL in acetonitrile, ampule of 1mL, certified reference material
  • 029-1ml
  • $ 154.00
  • DC Chemicals
  • Lacosamide >98%
  • 100 mg
  • $ 200.00
  • Cayman Chemical
  • Lacosamide ≥98%
  • 25mg
  • $ 124.00
  • Cayman Chemical
  • Lacosamide ≥98%
  • 10mg
  • $ 70.00
  • Cayman Chemical
  • Lacosamide ≥98%
  • 50mg
  • $ 228.00
  • Cayman Chemical
  • Lacosamide ≥98%
  • 5mg
  • $ 39.00
  • Biosynth Carbosynth
  • Lacosamide
  • 50 mg
  • $ 175.00
  • Biosynth Carbosynth
  • Lacosamide
  • 10 mg
  • $ 68.00
Total 204 raw suppliers
Chemical Property of Lacosamide Edit
Chemical Property:
  • Vapor Pressure:1.4E-11mmHg at 25°C 
  • Melting Point:141-143?C 
  • Refractive Index:1.52 
  • Boiling Point:536.4 °C at 760 mmHg 
  • PKA:14.19±0.46(Predicted) 
  • Flash Point:278.2 °C 
  • PSA:67.43000 
  • Density:1.12 g/cm3 
  • LogP:1.23570 
  • Storage Temp.:Refrigerator 
  • XLogP3:0.3
  • Hydrogen Bond Donor Count:2
  • Hydrogen Bond Acceptor Count:3
  • Rotatable Bond Count:6
  • Exact Mass:250.13174244
  • Heavy Atom Count:18
  • Complexity:275
Purity/Quality:

99.0% *data from raw suppliers

Lacosamide solution 1.0?mg/mL in acetonitrile, ampule of 1?mL, certified reference material, Cerilliant? *data from reagent suppliers

Safty Information:
  • Pictogram(s): F,Xn 
  • Hazard Codes:F,Xn 
  • Statements: 11-20/21/22-36 
  • Safety Statements: 16-26-36/37 
MSDS Files:

SDS file from LookChem

Useful:
  • Drug Classes:Anticonvulsants
  • Canonical SMILES:CC(=O)NC(COC)C(=O)NCC1=CC=CC=C1
  • Isomeric SMILES:CC(=O)N[C@H](COC)C(=O)NCC1=CC=CC=C1
  • Recent ClinicalTrials:Lacosamide in Migraine Prevention
  • Recent EU Clinical Trials:Combined effect of Pregabalin and Oxycodone, and Lacosamide and Oxycodone, on breathing: an exploratory study in healthy volunteers the POLO study
  • Recent NIPH Clinical Trials:Efficacy and safety of lacosamide in patients with erythromelalgia due to SCN9A gene mutation
  • Description Lacosamide (LCM), (SPM 927, (R)-2-acetamido-N-benzyl-3-methoxypropionamide, previously referred to as harkoseride or ADD 234037) is a member of a series of functionalized amino acids that were specifically synthesized as anticonvulsant or antiepileptic drug. It reduces the spread of seizure activity in the brain. Lacosamide appears to have a dual mode of action: selective enhancement of sodium channel inactivation and modulation of collapsin response mediator protein-2.? Compared to novel antiepileptic drugs, lacosamide has broader and higher efficacy, better tolerability, and improved pharmacokinetic properties. Lacosamide is in phase III clinical development for adjunctive treatment of patients with uncontrolled partial-onset seizures, and for monotherapy of patients with painful diabetic neuropathy. It is absorbed rapidly and completely after oral administration. Lacosamide has an elimination half-life of approximately 13 hours and a low potential for drug interactions. Additionally, lacosamide exhibits linear, dose-proportional pharmacokinetics with low intra- and interpatient variability. Lacosamide (licensed in 2008) is a third- generation AED known with the proprietary brand name of Vimpat? (UCB Pharma, Slough) in the UK and USA. Although epilepsy is a neurological disorder with varying etiology and severity, the common feature is unprovoked, recurring seizures. Whether classified as generalized, involving both cerebral hemispheres, or partial with only localized portions of brain participation at onset, effective treatment relies on accurate assessment of syndrome type to optimally decrease the frequency, duration, and severity of seizures. The latest weapon against partial onset epilepsy is lacosamide, formerly known as harkoseride and erlosamide. The data also indicate that lacosamide binds to collapsing response mediator protein 2 (CRMP2); CRMP2 is involved in neuronal differentiation, control of axonal outgrowth, and possibly epileptogenesis. Furthermore, lacosamide is heralded as having a dual mode of action as it has also displayed efficacy against diabetic neuropathy, possibly as a result of stabilization of neuronal hyperexcitability. Currently,lacosamide is approved as adjunctive treatment of partial onset seizures in patients 17 years or older and is in development as a monotherapy for epilepsy and for neuropathic pain. Lacosamide selectively enhances sodium channel slow inactivation without affecting fast inactivation. It is effective in multiple rodent models of seizure activity. The neuroprotective effects of lacosamide are also attributed to its ability to modulate collapsin response mediator protein 2 (CRMP-2), a member of the semaphorin signal transduction pathway. Formulations containing lacosamide have been used as an adjunctive or monotherapy for focal-onset seizures but, at higher doses, have a low potential for abuse. Lacosamide is regulated as a Schedule V compound in the United States.
  • Indications Epilepsy: Adjunctive treatment of focal seizures with or without secondary generalization.
  • Uses Lacosamide is an anticonvulsant and analgesic compound used for the treatment of partial-onset seizures and neuropathic pain. It can also used for the treatment of status epilepticus. Its analgesic effect is mediated by its inhibitory effect on sodium channels, which leads to neural membrane depolarization. Its interaction with the collapsin-response mediator protein 2 (CRMP-2 alias DRP-2) may also facilitate the above process, although the detailed mechanism remains to be elucidated. A potent anticonvulsant.
  • Clinical Use #N/A
  • Drug interactions Potentially hazardous interactions with other drugs Antidepressants: anticonvulsant effect antagonised; avoid with St John’s wort. Antimalarials: mefloquine antagonises anticonvulsant effect. Antipsychotics: anticonvulsant effect antagonised. Orlistat: possibly increased risk of convulsions.
Technology Process of Lacosamide

There total 140 articles about Lacosamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
With hydrogen; (-)-1,2-bis((2S,5S)-2,5-diphenylphospholano)ethane(1,5-cyclooctadiene)rhodium (I) tetrafluoroborate; In methanol; at 45 ℃; for 20h; under 7500.75 Torr; Inert atmosphere; Sealed vessel;
Guidance literature:
benzylamine; With trimethylaluminum; In dichloromethane; at 20 ℃; for 0.166667h; Inert atmosphere;
N-acetyl-β-methoxy-D-alanine ethyl ester; In dichloromethane; for 3h; Inert atmosphere;
DOI:10.1055/s-0036-1588093
Guidance literature:
With ytterbium(III) triflate; In toluene; at 110 ℃; for 20h; Reagent/catalyst; Solvent; Temperature;
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