Lacosamide (CED0003907)

Record Information

Version

1.0

Creation Date

2016-05-22 07:18:33 UTC

Update Date

2026-08-19 01:25:33 UTC

Accession Number

CHEM020665

Identification

Common Name

Lacosamide

Class

Small Molecule

Description

Lacosamide is an organic compound with the chemical formula C13H18N2O3 and an average molecular weight of 250.29 g/mol. Lacosamide belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. This compound is identified as being found in or released from one recorded source: healthcare, pharmaceuticals & veterinary products, specifically as an antiepileptic. Recorded exposure routes for the substance include oral and intravenous administration. Lacosamide interacts with five recorded protein targets. It acts as a blocker, inhibitor, or modulator of sodium channel protein type 3 subunit alpha (SCN3A), sodium channel protein type 9 subunit alpha (SCN9A), and sodium channel protein type 10 subunit alpha (SCN10A). Additionally, it targets dihydropyrimidinase-related protein 2 (DPYSL2) and one other protein.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Erlosamide	Kegg
Vimpat	Kegg
Ertosamide	MeSH
SPM-927	MeSH
Harkoseride	MeSH
(2R)-N-Benzyl-2-[(1-hydroxyethylidene)amino]-3-methoxypropanimidate	Generator

Chemical Formula

C₁₃H₁₈N₂O₃

Average Molecular Mass

250.294 g/mol

Monoisotopic Mass

250.132 g/mol

CAS Registry Number

175481-36-4

IUPAC Name

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

Traditional Name

lacosamide

SMILES

COC[C@@H](NC(C)=O)C(=O)NCC1=CC=CC=C1

InChI Identifier

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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids and derivatives

Alternative Parents

Substituents

N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Monocyclic benzene moiety
Benzenoid
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Dialkyl ether
Ether
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.46 g/L	ALOGPS
logP	0.18	ALOGPS
logP	-0.022	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	12.47	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.43 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	67.57 m³·mol⁻¹	ChemAxon
Polarizability	26.68 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-4980000000-2a17027f53ebaf4896d5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-4900000000-2e957be54fb955a3ee65	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052f-9300000000-7cc2e042432cc22c9158	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-1390000000-f8aadc28edb1f7eeb49a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-5970000000-150df46682060be97193	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a6u-9600000000-b8f90f0e5654c8d52b90	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2348.0	Log mg/kg	[1300:4200]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
371	Antiepileptics	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

2 pathways

Lacosamide Action Pathway

Lacosamide Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Peptidyl-glycine alpha-amidating monooxygenase	P19021	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	23.5105
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	26.4687
Click to view 3D structure	Carbonic anhydrase 5A, mitochondrial	P35218	Humans	Predicted (SEA)	8.95266
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	29.5049
Click to view 3D structure	Carbonic anhydrase 7	P43166	Humans	Predicted (SEA)	16.9711
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	27.0137
Click to view 3D structure	Aminopeptidase N	P15145	Sus scrofa	Predicted (SEA)	6.46149
Click to view 3D structure	Carbonic anhydrase 6	P23280	Humans	Predicted (SEA)	11.366
Click to view 3D structure	Carbonic anhydrase 14	Q9ULX7	Humans	Predicted (SEA)	16.1148
Click to view 3D structure	Carbonic anhydrase 13	Q8N1Q1	Humans	Predicted (SEA)	3.73676
Click to view 3D structure	Carbonic anhydrase 3	P07451	Humans	Predicted (SEA)	2.25763
Click to view 3D structure	Carbonic anhydrase 5B, mitochondrial	Q9Y2D0	Humans	Predicted (SEA)	16.8933
Click to view 3D structure	Cathepsin S	P25774	Humans	Predicted (SEA)	28.6485
Click to view 3D structure	Cathepsin K	P43235	Humans	Predicted (SEA)	25.3788
Click to view 3D structure	Procathepsin L	P25975	Bos taurus	Predicted (SEA)	9.03051
Click to view 3D structure	Carbonic anhydrase 4	P22748	Humans	Predicted (SEA)	21.175
Click to view 3D structure	Sodium channel protein type 9 subunit alpha	Q15858	Humans	Predicted (SEA)	74.6574
Click to view 3D structure	Carbonic anhydrase 15	Q99N23	Mus musculus	Predicted (SEA)	12.5337
Click to view 3D structure	Procathepsin L	P07711	Humans	Predicted (SEA)	47.0209
Click to view 3D structure	Aminopeptidase N	P15144	Humans	Predicted (SEA)	19.9294
Click to view 3D structure	Histone deacetylase 1	Q13547	Humans	Predicted (SEA)	104.707
Click to view 3D structure	Cathepsin B	P07858	Humans	Predicted (SEA)	47.6437
Click to view 3D structure	Papain	P00784	Carica papaya	Predicted (SEA)	26.1573
Click to view 3D structure	Cruzipain	P25779	Trypanosoma cruzi	Predicted (SEA)	22.8098