<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 07:18:33 UTC</creation_date>
  <update_date>2026-08-19 01:25:33 UTC</update_date>
  <accession/>
  <common_name>Lacosamide</common_name>
  <class>SmallMolecule</class>
  <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 &amp; 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.</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C13H18N2O3</chemical_formula>
  <average_molecular_weight>250.2936</average_molecular_weight>
  <monisotopic_moleculate_weight>250.131742452</monisotopic_moleculate_weight>
  <iupac_name>(2R)-N-benzyl-2-acetamido-3-methoxypropanamide</iupac_name>
  <traditional_iupac>lacosamide</traditional_iupac>
  <cas_registry_number>175481-36-4</cas_registry_number>
  <smiles>COC[C@@H](NC(C)=O)C(=O)NCC1=CC=CC=C1</smiles>
  <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>
  <inchikey>VPPJLAIAVCUEMN-GFCCVEGCSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids and derivatives</direct_parent>
    <alternate_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alpha amino acid amides</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Alpha-amino acid amide</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors/>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Lacosamide Action Pathway</name>
      <smpdb_id>SMP0126276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lacosamide Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0144018</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-0.022</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.65e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.022</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-N-benzyl-2-acetamido-3-methoxypropanamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>250.2936</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>250.131742452</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC[C@@H](NC(C)=O)C(=O)NCC1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C13H18N2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>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</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VPPJLAIAVCUEMN-GFCCVEGCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>67.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>67.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f3bb3c16ce0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB06218</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>21634109</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>10266281</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
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  </targets>
</compound>
