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Compound Detail

CHEMBL58323

LACOSAMIDE
💊 Approved Drug
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💊 Approved Drug
COC[C@@H](NC(C)=O)C(=O)NCc1ccccc1

Basic Information

ChEMBL ID CHEMBL58323
Name LACOSAMIDE
Phase Approved
Structure Type MOL
InChI Key VPPJLAIAVCUEMN-GFCCVEGCSA-N
Therapeutic ✓ Yes

Known Names

(r)-lacosamide 1 ADD 243037 ADD-243037 ADD243037 Erlosamide Lacosamida Lacosamide Lacosamide accord Lacosamide adroiq Lacosamide cv Lacosamide ucb Motpoly +5 more
18
Targets
23
Activities
2
Assay Types
0
PK Parameters
20
Publications
17
Known Names
20
Indications
1
Mechanisms

Molecular Properties

250.3
MW (Da)
0.45
ALogP
3
HBA
2
HBD
67.4
PSA (Ų)
0.77
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2008
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Natural Product
USAN Year 2005

Extended Properties

Molecular Formula C13H18N2O3
MW 250.30
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness -0.66

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Sodium channel alpha subunit blocker BLOCKER Sodium channel alpha subunit

Indications

Epilepsies, Partial Epilepsy Epilepsy Seizures Anxiety Dementia Depressive Disorder Diabetic Neuropathies Erythromelalgia Migraine Disorders Schizophrenia Sciatica Status Epilepticus Alcoholism Brain Neoplasms Fibromyalgia Neuralgia Neuralgia, Postherpetic Osteoarthritis Paraganglioma

ATC Classification

N03AX18
lacosamide
Level 1: NERVOUS SYSTEM
Level 2: ANTIEPILEPTICS

Activity Summary

Ki 13 meas. best 6.48
IC50 10 meas. best 6.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium channel protein type 9 subunit alpha
CHEMBL4296
IC50 6.74 6.74 182.0 1
Carbonic anhydrase 2
CHEMBL205
Ki 6.48 6.48 331.0 1
Carbonic anhydrase 5B, mitochondrial
CHEMBL3969
Ki 6.47 6.47 341.0 1
Carbonic anhydrase 9
CHEMBL3594
Ki 6.45 6.45 353.0 1
Carbonic anhydrase 1
CHEMBL261
Ki 6.44 6.44 362.0 1
Carbonic anhydrase 3
CHEMBL2885
Ki 6.43 6.43 374.0 1
Carbonic anhydrase 6
CHEMBL3025
Ki 6.38 6.38 412.0 1
Sodium channel protein type 3 subunit alpha
CHEMBL4966
IC50 6.38 6.38 415.0 2
Carbonic anhydrase 15
CHEMBL5973
Ki 6.34 6.34 461.0 1
Carbonic anhydrase 14
CHEMBL3510
Ki 6.33 6.33 473.0 1
Carbonic anhydrase 4
CHEMBL3729
Ki 6.28 6.28 525.0 1
Carbonic anhydrase 13
CHEMBL3912
Ki 5.92 5.92 1210.0 1
Carbonic anhydrase 12
CHEMBL3242
Ki 5.43 5.43 3713.0 1
Carbonic anhydrase 7
CHEMBL2326
Ki 5.35 5.35 4446.0 1
Carbonic anhydrase 5A, mitochondrial
CHEMBL4789
Ki 5.34 5.34 4565.0 1
Sodium channel protein type 10 subunit alpha
CHEMBL4017
IC50 4.8 4.8 16000.0 1
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL1940
IC50 4.3 4.3 50118.7 1
Unchecked
CHEMBL612545
IC50 4.07 4.07 85000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium channel protein type 9 subunit alpha IC50 = 182.0 nM 6.74 Binding affinity to human inactivated voltage-gated Na channel 1.7 expressed in ... 23121096
Carbonic anhydrase 2 Ki = 331.0 nM 6.48 Inhibition of human recombinant CA2 by stopped flow CO2 hydrase assay 20028100
Carbonic anhydrase 5B, mitochondrial Ki = 341.0 nM 6.47 Inhibition of human recombinant CA5B by stopped flow CO2 hydrase assay 20028100
Carbonic anhydrase 9 Ki = 353.0 nM 6.45 Inhibition of human recombinant CA9 by stopped flow CO2 hydrase assay 20028100
Carbonic anhydrase 1 Ki = 362.0 nM 6.44 Inhibition of human recombinant CA1 by stopped flow CO2 hydrase assay 20028100
Carbonic anhydrase 3 Ki = 374.0 nM 6.43 Inhibition of human recombinant CA3 by stopped flow CO2 hydrase assay 20028100
Sodium channel protein type 3 subunit alpha IC50 = 415.0 nM 6.38 Binding affinity to rat inactivated voltage-gated Na channel 1.3 expressed in hu... 23121096
Carbonic anhydrase 6 Ki = 412.0 nM 6.38 Inhibition of human recombinant CA6 by stopped flow CO2 hydrase assay 20028100
Sodium channel protein type 3 subunit alpha IC50 = 415.0 nM 6.38 Inhibition of rat NaV1.3 expressed in HEK293 cells at -80V holding potential by ... 30108836
Carbonic anhydrase 15 Ki = 461.0 nM 6.34 Inhibition of mouse recombinant CA15 by stopped flow CO2 hydrase assay 20028100
Carbonic anhydrase 14 Ki = 473.0 nM 6.33 Inhibition of human recombinant CA14 by stopped flow CO2 hydrase assay 20028100
Carbonic anhydrase 4 Ki = 525.0 nM 6.28 Inhibition of human recombinant CA4 by stopped flow CO2 hydrase assay 20028100
Carbonic anhydrase 13 Ki = 1210.0 nM 5.92 Inhibition of human recombinant CA13 by stopped flow CO2 hydrase assay 20028100
Carbonic anhydrase 12 Ki = 3713.0 nM 5.43 Inhibition of human recombinant CA12 by stopped flow CO2 hydrase assay 20028100
Carbonic anhydrase 7 Ki = 4446.0 nM 5.35 Inhibition of human recombinant CA7 by stopped flow CO2 hydrase assay 20028100
Carbonic anhydrase 5A, mitochondrial Ki = 4565.0 nM 5.34 Inhibition of human recombinant CA5A by stopped flow CO2 hydrase assay 20028100
Sodium channel protein type 10 subunit alpha IC50 = 16000.0 nM 4.8 Binding affinity to voltage-gated Na channel 1.8 in Sprague-Dawley rat L4/L5 DRG... 23121096
Voltage-dependent L-type calcium channel subunit alpha-1C IC50 = 50118.72 nM 4.3 Inhibition of long-lasting type calcium current (hICa) in Chinese Hamster Ovary ... 25087753
Unchecked IC50 = 85000.0 nM 4.07 Inhibition of Na+ channel in mouse CAD cells assessed as slow inactivation by wh... 23772678

Literature References

Data from ChEMBL 36 via Core Engine