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Compound Detail

CHEMBL741

LAMOTRIGINE
💊 Approved Drug
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💊 Approved Drug
Nc1nnc(-c2cccc(Cl)c2Cl)c(N)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL741
Name LAMOTRIGINE
Phase Approved
Structure Type MOL
InChI Key PYZRQGJRPPTADH-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

BW 430C BW-430C Lamictal Lamictal cd Lamictal odt Lamictal xr Lamotrigina Lamotrigine NSC-759171
12
Targets
36
Activities
2
Assay Types
13
PK Parameters
20
Publications
9
Known Names
20
Indications
1
Mechanisms

Molecular Properties

256.1
MW (Da)
2.01
ALogP
5
HBA
2
HBD
90.7
PSA (Ų)
0.81
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1994
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -trigine
USAN Year 1985

Extended Properties

Molecular Formula C9H7Cl2N5
MW 256.10
Aromatic Rings 2
Heavy Atoms 16
NP-Likeness -1.11

Mechanism of Action

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

Indications

Bipolar Disorder Bipolar Disorder Depressive Disorder Depressive Disorder Epilepsies, Partial Epilepsy Epilepsy, Tonic-Clonic Epilepsy, Tonic-Clonic Lennox Gastaut Syndrome Seizures Anxiety Dementia Epilepsy, Absence Feeding and Eating Disorders Mood Disorders Obesity Pain Peripheral Nervous System Diseases Schizophrenia Alcoholism

ATC Classification

N03AX09
lamotrigine
Level 1: NERVOUS SYSTEM
Level 2: ANTIEPILEPTICS

Drug Warnings

Black Box Warning
dermatological toxicity
Country: United States

Activity Summary

IC50 33 meas. best 5.58
Ki 3 meas. best 4.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 5.58 4.625 2600.0 8
Sodium channel protein type 2 subunit alpha
CHEMBL4187
 IC50 5.0 4.885 10000.0 2
Dihydrofolate reductase
CHEMBL1809
 Ki 4.82 4.82 15240.0 1
Sodium channel protein type 4 subunit alpha
CHEMBL2072
 Ki 4.77 4.77 17000.0 1
Sodium channel protein type 9 subunit alpha
CHEMBL4296
 IC50 4.77 4.77 17000.0 1
Sodium channel protein type 3 subunit alpha
CHEMBL5163
 IC50 4.77 4.77 17000.0 1
Sodium channel protein type 10 subunit alpha
CHEMBL4017
 IC50 4.6 4.6 25000.0 1
Nucleic Acid
CHEMBL345
 Ki 4.54 4.54 29200.0 1
Sodium channel alpha subunits; brain (Types I, II, III)
CHEMBL2095171
 IC50 4.51 4.51 31000.0 1
Sodium channel protein type 2 subunit alpha
CHEMBL3399
 IC50 4.46 4.46 35000.0 2
Sodium channel protein type 5 subunit alpha
CHEMBL1980
 IC50 4.4 4.2033 39810.7 3
Sodium channel protein type 10 subunit alpha
CHEMBL5451
 IC50 4.02 4.015 96000.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 1.0 mL.min-1.kg-1 Rattus norvegicus
CL 0.6 mL.min-1.kg-1 Homo sapiens
CL 0.6 mL.min-1.kg-1 Homo sapiens
CL 1.4 mL.min-1.kg-1 Mus musculus
CL 1.4 uL.min-1.(10^6cells)-1 Homo sapiens
Cmax 13666.54 nM Rattus norvegicus
F 80.0 % Homo sapiens
F 79.0 % Rattus norvegicus
Fu 0.51 - Rattus norvegicus
Fu 0.21 - Rattus norvegicus
Fu 0.45 - Homo sapiens
T1/2 10.1 hr Mus musculus
Vd 4.6 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 2600.0 nM 5.58 Displacement of [3H]BW202W92 from voltage-gated sodium channel in Wistar rat for... 19341281
Unchecked IC50 = 8100.0 nM 5.09 Inhibition of human aquaporin 4 M23 isoform expressed in Xenopus laevis oocytes 18178093
Sodium channel protein type 2 subunit alpha IC50 = 10000.0 nM 5.0 Inhibition of human recombinant Nav1.2 channel expressed in HEK293 cells by whol... 18501613
Dihydrofolate reductase Ki = 15240.0 nM 4.82 Inhibition of Escherichia coli DHFR assessed as NADP formation by quadratic Morr... 26414808
Sodium channel protein type 2 subunit alpha IC50 = 17000.0 nM 4.77 Inhibition of human Nav1.2 expressed in SHSY5Y cells assessed as reduction in bl... 26101568
Sodium channel protein type 3 subunit alpha IC50 = 17000.0 nM 4.77 Inhibition of human Nav1.3 expressed in SHSY5Y cells assessed as reduction in bl... 26101568
Sodium channel protein type 9 subunit alpha IC50 = 17000.0 nM 4.77 Inhibition of human Nav1.7 expressed in SHSY5Y cells assessed as reduction in bl... 26101568
Sodium channel protein type 4 subunit alpha Ki = 17000.0 nM 4.77 Affinity for inactive human SkM1 sodium channel expressed in HEK293 cells 14998340
Unchecked IC50 = 21000.0 nM 4.68 Inhibition of veratridine-induced guanidine flux in cardiac voltage-gated sodium... 11170622
Sodium channel protein type 10 subunit alpha IC50 = 25000.0 nM 4.6 Blockade of Nav1.8 channel in rat dorsal root ganglion neurons assessed as inhib... 18501613
Unchecked IC50 = 25820.0 nM 4.59 PUBCHEM_BIOASSAY: A counter screen for small molecule screen for inhibitors of t... -
Nucleic Acid Ki = 29200.0 nM 4.54 Dissociation constant for binding to inactivated state of rat brain NaIIa (rNav1... 15293999
Sodium channel alpha subunits; brain (Types I, II, III) IC50 = 31000.0 nM 4.51 Concentration required to inhibit [3H]BTX binding to Sodium channel of rat brain 15177465
Unchecked IC50 = 32987.0 nM 4.48 PUBCHEM_BIOASSAY: A screen for inhibitors of the PhoP region in Salmonella Typhi... -
Sodium channel protein type 2 subunit alpha IC50 = 35000.0 nM 4.46 Inhibition of rat Nav1.2 expressed in CHL1610 cells at -67 to -107 mV after 2 to... 24205976
Sodium channel protein type 2 subunit alpha IC50 = 35000.0 nM 4.46 Inhibition of rat Nav1.2 channel expressed in chinese hamster CHL1610 cells at p... 19388676
Sodium channel protein type 5 subunit alpha IC50 = 39810.72 nM 4.4 Inhibition of fast sodium current (INa) in HEK293 cells transfected with human N... 25087753
Unchecked IC50 = 60490.0 nM 4.22 PUBCHEM_BIOASSAY: A Counter Screen to identiry small molecule screen for inhibit... -
Sodium channel protein type 5 subunit alpha IC50 = 62000.0 nM 4.21 Inhibition of human recombinant Nav1.5 channel expressed in HEK293 cells by whol... 18501613
Unchecked IC50 = 66350.0 nM 4.18 PUBCHEM_BIOASSAY: A screen for inhibitors of the PhoP region in Salmonella Typhi... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 332
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 58
17451232 10.1021/jm061431g Rattus norvegicus 40
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
18403060 10.1016/j.ejmech.2008.01.036 Mus musculus 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
18501613 10.1016/j.bmc.2008.05.003 Rattus norvegicus 8
18572411 10.1016/j.bmc.2008.06.005 Aquaporin-4 7
20070106 10.1021/jm901371v Homo sapiens 7
29681486 10.1016/j.bmc.2018.04.023 Mus musculus 6
9484507 10.1021/jm970599m Mus musculus 5
- 10.1007/s00044-013-0843-6 Mus musculus 4
26414808 10.1016/j.ejmech.2015.08.021 Dihydrofolate reductase 4
19341281 10.1021/jm801180p Sodium channel protein type 2 subunit alpha 4
19764786 10.1021/jm901036q Plasma 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
26690914 10.1016/j.bmc.2015.11.021 Mus musculus 4

Data from ChEMBL 36 via Core Engine