CARBAMAZEPINE

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC N03AF01
UNII 33CM23913M
EPA CompTox DTXSID4022731

Structure

InChI Key FFGPTBGBLSHEPO-UHFFFAOYSA-N
Smiles NC(=O)N1c2ccccc2C=Cc2ccccc21
InChI
InChI=1S/C15H12N2O/c16-15(18)17-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)17/h1-10H,(H2,16,18)

Physicochemical Descriptors

Property Name Value
Molecular Formula C15H12N2O
Molecular Weight 236.27
AlogP 3.39
Hydrogen Bond Acceptor 1.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 0.0
Polar Surface Area 46.33
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 18.0

Bioactivity

Mechanism of Action Action Reference
Sodium channel alpha subunit blocker BLOCKER PubMed PubMed
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
- - - - 8
Ion channel Ligand-gated ion channel P2X receptor
- - - - 35
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- 22000 - 32700 23-65
Membrane receptor Frizzled family G protein-coupled receptor
- - 16800 - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 13-122
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 8
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 8.0 %
Percent inhibition of 22Na+ uptake by voltage sensitive sodium channel of rat cortical synaptosomes at 100 uM Rattus norvegicus 44.3 %
Percent inhibition of 22Na+ uptake by voltage sensitive sodium channel of rat cortical synaptosomes at 30 uM Rattus norvegicus 22.6 %
Percent inhibition of 22Na+ uptake by voltage sensitive sodium channel of rat cortical synaptosomes at 300 uM Rattus norvegicus 64.8 %
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM Cavia porcellus 1.6 %
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 8.4 %
Antagonist activity at human 5HT3A receptor expressed in HEK293 cells assessed as inhibition of serotonin-induced inward Na+ current at >= 10 uM Homo sapiens 50.0 %
Anticonvulsant activity in mouse assessed as inhibition of PTZ-induced clonic seizure at 50 mg/kg, ip administered 30 mins prior to PTZ challenge measured after 0.5 hrs Mus musculus 100.0 %
Anticonvulsant activity in mouse assessed as inhibition of PTZ-induced tonic seizure at 50 mg/kg, ip administered 30 mins prior to PTZ challenge measured after 0.5 hrs Mus musculus 0.0 %
Anticonvulsant activity in mouse assessed as inhibition of isoniazid-induced clonic seizure at 50 mg/kg, ip administered 30 mins prior to isoniazid challenge measured after 0.5 hrs Mus musculus 40.0 %
Anticonvulsant activity in mouse assessed as inhibition of isoniazid-induced tonic seizure at 50 mg/kg, ip administered 30 mins prior to isoniazid challenge measured after 0.5 hrs Mus musculus 0.0 %
Anticonvulsant activity in mouse assessed as inhibition of 3-mercaptopropionic acid-induced clonic seizure at 50 mg/kg, ip administered 30 mins prior to 3-mercaptopropionic acid challenge measured after 0.5 hrs Mus musculus 80.0 %
Anticonvulsant activity in mouse assessed as inhibition of 3-mercaptopropionic acid-induced tonic seizure at 50 mg/kg, ip administered 30 mins prior to 3-mercaptopropionic acid challenge measured after 0.5 hrs Mus musculus 0.0 %
Anticonvulsant activity in mouse assessed as inhibition of thiosemicarbazide-induced clonic seizure at 50 mg/kg, ip administered 30 mins prior to thiosemicarbazide challenge measured after 2.5 hrs Mus musculus 90.0 %
Anticonvulsant activity in mouse assessed as inhibition of thiosemicarbazide-induced tonic seizure at 50 mg/kg, ip administered 30 mins prior to thiosemicarbazide challenge measured after 2.5 hrs Mus musculus 0.0 %
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 13.3 %
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 23.2 %
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 17.3 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 121.62 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 99.43 %
Antagonist activity at human P2X4 receptor expressed in human 1321N1 cells assessed as inhibition of ATP-induced cytosolic calcium influx at 100 uM preincubated for 30 mins followed by ATP addition by Fluo-4 AM dye-based fluorescence assay Homo sapiens 35.0 %
Anticonvulsant activity in Kunming mouse assessed as protection against sc-PTZ-induced clonic seizures 50 mg/kg, sc administered 30 mins before PTZ injection Mus musculus 0.0 %
Anticonvulsant activity in Kunming mouse assessed as protection against sc-PTZ-induced tonic seizures 50 mg/kg, sc administered 30 mins before PTZ injection Mus musculus 100.0 %
Anticonvulsant activity in Kunming mouse assessed as protection against sc-PTZ-induced mortality 50 mg/kg, sc administered 30 mins before PTZ injection Mus musculus 80.0 %
Time dependent inhibition of CYP1A2 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2B6 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C9 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C19 in human liver microsomes at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2D6 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C8 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP3A4 (unknown origin) at 10 uM by LC/MS system Homo sapiens 10.0 %
Inhibition of [3H]BTX binding to sodium channel site 2 in rat cerebral cortex synaptosomes at 100 uM incubated for 60 mins by scintillation counting based radioligand displacement assay Rattus norvegicus 17.4 %
Inhibition of [3H]BTX binding to sodium channel site 2 in rat cerebral cortex synaptosomes at 10 uM incubated for 60 mins by scintillation counting based radioligand displacement assay Rattus norvegicus 4.6 %
Inhibition of [3H]BTX binding to sodium channel site 2 in rat cerebral cortex synaptosomes at 1 uM incubated for 60 mins by scintillation counting based radioligand displacement assay Rattus norvegicus 2.7 %
Inhibition of [3H]BTX binding to sodium channel site 2 in rat cerebral cortex synaptosomes at 500 uM incubated for 60 mins by scintillation counting based radioligand displacement assay Rattus norvegicus 33.6 %
Displacement of [3H]Batrachotoxinin from sodium channel site 2 in rat cerebral cortex at 100 uM after 60 mins by scintillation counting method Rattus norvegicus 17.4 %
Displacement of [3H]Batrachotoxinin from sodium channel site 2 in rat cerebral cortex at 500 uM after 60 mins by scintillation counting method Rattus norvegicus 33.6 %
Displacement of [3H]Batrachotoxinin from voltage-sensitive sodium channel site 2 in rat cerebral cortex synaptoneurosomes at 500 uM measured after 60 mins by scintillation counting method Rattus norvegicus 33.6 %
Displacement of [125I]omega-Conotoxin GVIA from N-type calcium channel in rat cerebral cortex synaptoneurosomes at 100 uM measured after 30 mins by scintillation counting method Rattus norvegicus -2.9 %
Displacement of [125I]omega-Conotoxin GVIA from N-type calcium channel in rat cerebral cortex synaptoneurosomes at 200 uM measured after 30 mins by scintillation counting method Rattus norvegicus 1.9 %
Displacement of [3H]diltiazem from L-type calcium channel diltiazem binding site in rat cerebral cortex synaptoneurosomes at 100 uM measured after 120 mins by scintillation counting method Rattus norvegicus 1.1 %
Displacement of [3H]diltiazem from L-type calcium channel diltiazem binding site in rat cerebral cortex synaptoneurosomes at 200 uM measured after 120 mins by scintillation counting method Rattus norvegicus 7.3 %
Displacement of [3H]nitrendipine from L-type calcium channel dihydropyridine site in rat cerebral cortex synaptoneurosomes at 100 uM measured after 90 mins by scintillation counting method Rattus norvegicus 2.6 %
Displacement of [3H]nitrendipine from L-type calcium channel dihydropyridine site in rat cerebral cortex synaptoneurosomes at 200 uM measured after 90 mins by scintillation counting method Rattus norvegicus 3.6 %
Displacement of [3H]D888 from L-type calcium channel verapamil binding site in rat cerebral cortex synaptoneurosomes at 100 uM measured after 120 mins by scintillation counting method Rattus norvegicus 8.8 %
Displacement of [3H]D888 from L-type calcium channel verapamil binding site in rat cerebral cortex synaptoneurosomes at 200 uM measured after 120 mins by scintillation counting method Rattus norvegicus 7.5 %
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 10.71 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli -3.33 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 5.59 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 9.78 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 21.57 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 4.45 %
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 -2.39 %
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 3.04 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 19.35 %
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 0.62 % 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 0.62 %

Environmental Exposure

Environmental Exposure Map
Countries
Bangladesch
Croatia
Czech Republic
Germany
Hungary
India
Romania
Serbia
Slovakia
Slovenia
South Africa
Spain
Sweden
USA
Vietnam

Cross References

Resources Reference
ChEBI 3387
ChEMBL CHEMBL108
DrugBank DB00564
DrugCentral 489
FDA SRS 33CM23913M
Human Metabolome Database HMDB0014704
Guide to Pharmacology 5339
KEGG C06868
PDB N6W
PharmGKB PA448785
PubChem 2554
SureChEMBL SCHEMBL21639
ZINC ZINC000000004785
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