LAMOTRIGINE

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC N03AX09
UNII U3H27498KS
EPA CompTox DTXSID2023195

Structure

InChI Key PYZRQGJRPPTADH-UHFFFAOYSA-N
Smiles Nc1nnc(-c2cccc(Cl)c2Cl)c(N)n1
InChI
InChI=1S/C9H7Cl2N5/c10-5-3-1-2-4(6(5)11)7-8(12)14-9(13)16-15-7/h1-3H,(H4,12,13,14,16)

Physicochemical Descriptors

Property Name Value
Molecular Formula C9H7Cl2N5
Molecular Weight 256.1
AlogP 2.01
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 1.0
Polar Surface Area 90.71
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 16.0

Bioactivity

Mechanism of Action Action Reference
Sodium channel alpha subunit blocker BLOCKER PubMed PubMed PubMed DailyMed
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 1 subunit alpha
Organism : Homo sapiens
P35498 ENSG00000144285
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 4 subunit alpha
Organism : Homo sapiens
P35499 ENSG00000007314
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 5 subunit alpha
Organism : Homo sapiens
Q14524 ENSG00000183873
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 9 subunit alpha
Organism : Homo sapiens
Q15858 ENSG00000169432
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 2 subunit alpha
Organism : Homo sapiens
Q99250 ENSG00000136531
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 3 subunit alpha
Organism : Homo sapiens
Q9NY46 ENSG00000153253
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 11 subunit alpha
Organism : Homo sapiens
Q9UI33 ENSG00000168356
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 8 subunit alpha
Organism : Homo sapiens
Q9UQD0 ENSG00000196876
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 10 subunit alpha
Organism : Homo sapiens
Q9Y5Y9 ENSG00000185313
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
- - - 15240 11
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- 39811-100000 - 17000 4-35
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 14
Assay Description Organism Bioactivity Reference
Inhibition of beta-lactamase at 100 uM None 5.0 %
Inhibition of chymotrypsin at 250 uM unidentified 5.0 %
Inhibition of malate dehydrogenase (MDH) at 400 uM None 11.0 %
Percent inhibition of convulsions in audiogenic DBA/2 mice at dose 10 mg/kg Mus musculus 71.0 %
Inhibition of human Nav1.2 channel expressed in HEK cells at 10 uM by patch-clamp electrophysiology method Homo sapiens 12.1 %
Inhibition of human Nav1.2 channel expressed in HEK cells at 100 uM by patch-clamp electrophysiology method Homo sapiens 35.1 %
Inhibition of human Nav1.1 expressed in HEK293 cells assessed as change in membrane potential using MP-red voltage sensitive dye at 10 uM Homo sapiens 44.0 %
Inhibition of human Nav1.3 expressed in HEK293 cells assessed as change in membrane potential using MP-red voltage sensitive dye at 10 uM Homo sapiens 22.0 %
Inhibition of human Nav1.4 expressed in HEK293 cells assessed as change in membrane potential using MP-red voltage sensitive dye at 10 uM Homo sapiens 21.0 %
Inhibition of human Nav1.5 expressed in HEK293 cells assessed as change in membrane potential using MP-red voltage sensitive dye at 10 uM Homo sapiens 40.0 %
Inhibition of human Nav1.6 expressed in HEK293 cells assessed as change in membrane potential using MP-red voltage sensitive dye at 10 uM Homo sapiens 23.0 %
Inhibition of human Nav1.7 expressed in HEK293 cells assessed as change in membrane potential using MP-red voltage sensitive dye at 10 uM Homo sapiens 45.0 %
Inhibition of human Nav1.8 expressed in HEK293 cells assessed as change in membrane potential using MP-red voltage sensitive dye at 10 uM Homo sapiens 46.0 %
Use-dependent inhibition of human Nav1.2 expressed in HEK293 cells at 30 uM using double-pulse protocol by patch clamp technique Homo sapiens 4.1 %
Use-dependent inhibition of human Nav1.2 expressed in HEK293 cells at 100 uM using double-pulse protocol by patch clamp technique Homo sapiens 18.1 %
Inhibition of human Nav1.2 expressed in HEK293 cells assessed as change in membrane potential at 30 uM by patch clamp technique Homo sapiens 7.9 %
Inhibition of human Nav1.2 expressed in HEK293 cells assessed as change in membrane potential at 100 uM by patch clamp technique Homo sapiens 17.0 %
Inhibition of human aquaporin 4 M23 isoform expressed in Xenopus laevis oocytes at 20 uM Homo sapiens 54.0 %
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 24.9 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 14.5 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 13.6 %
Neuroprotective activity in oxygen/glucose deprivation-induced Wistar rat hippocampal slice assessed as inhibition of cell death by measuring ATP level at 30 uM normalized to tetrodotoxin Rattus norvegicus 33.0 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 8.71 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 4.49 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 6.26 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 7.8 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 21.58 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 3.32 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -2.92 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -7.33 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 8.522 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.13 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.13 %

Environmental Exposure

Environmental Exposure Map
Countries
Croatia
Czech Republic
Germany
Hungary
Romania
Serbia
Slovakia
Slovenia
Sweden

Cross References

Resources Reference
ChEBI 6367
ChEMBL CHEMBL741
DrugBank DB00555
DrugCentral 1540
FDA SRS U3H27498KS
Human Metabolome Database HMDB0014695
Guide to Pharmacology 2622
KEGG D00354
PharmGKB PA450164
PubChem 3878
SureChEMBL SCHEMBL35439
ZINC ZINC000000013156
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