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Compound Detail

CHEMBL108

CARBAMAZEPINE
💊 Approved Drug
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💊 Approved Drug
NC(=O)N1c2ccccc2C=Cc2ccccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL108
Name CARBAMAZEPINE
Phase Approved
Structure Type MOL
InChI Key FFGPTBGBLSHEPO-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Arbil mr Biston Carbagen sr Carbamazepina Carbamazepine Carbamazepine anhydrous Carbamazepine extended release Carbamazepinum Carbatrol Carnexiv Epimaz Epimaz ret +18 more
9
Targets
22
Activities
4
Assay Types
30
PK Parameters
20
Publications
30
Known Names
19
Indications
1
Mechanisms

Molecular Properties

236.3
MW (Da)
3.39
ALogP
1
HBA
1
HBD
46.3
PSA (Ų)
0.75
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1968
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -pine
USAN Year 1965

Extended Properties

Molecular Formula C15H12N2O
MW 236.27
Aromatic Rings 2
Heavy Atoms 18
NP-Likeness -0.13

Mechanism of Action

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

Indications

Bipolar Disorder Bipolar Disorder Epilepsies, Partial Epilepsy Glossopharyngeal Nerve Diseases Seizures Trigeminal Neuralgia Anxiety Dementia Depressive Disorder Schizophrenia Cocaine-Related Disorders Epilepsy, Reflex HIV Infections Nausea Substance-Related Disorders Hepatitis B, Chronic Parkinson Disease Severe Acute Respiratory Syndrome

ATC Classification

N03AF01
carbamazepine
Level 1: NERVOUS SYSTEM
Level 2: ANTIEPILEPTICS

Drug Warnings

Black Box Warning
hematological toxicity
Country: United States
Black Box Warning
dermatological toxicity
Country: United States
Black Box Warning
gastrointestinal toxicity
Country: United States

Activity Summary

IC50 12 meas. best 4.66
EC50 4 meas. best 5.92
Kd 3 meas. best 4.78
Ki 3 meas. best 4.49

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 EC50 5.92 5.92 1200.0 1
Mus musculus
CHEMBL375
 EC50 5.25 5.25 5600.0 1
Frizzled-8
CHEMBL4523332
 Kd 4.78 4.78 16800.0 1
Sodium channel protein type 9 subunit alpha
CHEMBL4296
 IC50 4.66 4.35 22000.0 2
ADMET
CHEMBL612558
 Kd 4.62 4.62 24200.0 1
Hepatocyte
CHEMBL613690
 EC50 4.58 4.58 26000.0 1
Unchecked
CHEMBL612545
 IC50 4.52 4.52 30000.0 1
Sodium channel protein type 9 subunit alpha
CHEMBL4296
 Ki 4.49 4.49 32700.0 1
Nucleic Acid
CHEMBL345
 Ki 4.34 4.34 46100.0 1
Sodium channel protein type 5 subunit alpha
CHEMBL1980
 IC50 4.33 4.33 46800.0 1
Sodium channel protein type 4 subunit alpha
CHEMBL2072
 Ki 4.28 4.28 52000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2550.0 ng.hr.mL-1 Rattus norvegicus
AUC 2540.0 ng.hr.mL-1 Rattus norvegicus
AUC 458.0 ng.hr.mL-1 Rattus norvegicus
AUC 456.0 ng.hr.mL-1 Rattus norvegicus
AUC 2280.0 ng.hr.mL-1 Rattus norvegicus
AUC 2270.0 ng.hr.mL-1 Rattus norvegicus
CL 5.25 uL.min-1.(10^6cells)-1 Homo sapiens
CL 7.0 mL.min-1.g-1 Homo sapiens
CL 19.95 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL - - Homo sapiens
CL - - Homo sapiens
CL 6.0 mL.min-1.g-1 Homo sapiens
CL 7.0 mL.min-1.g-1 Mus musculus
F 80.0 % Homo sapiens
F 70.0 % Homo sapiens
F 70.0 % Homo sapiens
F 90.0 % Homo sapiens
F 90.0 % Homo sapiens
Fu 0.97 - Homo sapiens
Fu 0.119 - Rattus norvegicus
Fu 0.132 - Sus scrofa
Fu 0.171 - Homo sapiens
Fu 0.185 - Macaca fascicularis
Fu 0.159 - Canis lupus familiaris
Fu 0.128 - Cavia porcellus
Fu 0.173 - Mus musculus
Fu 0.124 - Rattus norvegicus
Fu 0.299 - Not specified
Fu 0.288 - Not specified
Fu 0.291 - Not specified

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked EC50 = 1200.0 nM 5.92 Displacement of [3H]nitrendipine from voltage-dependent calcium channel in rat b... 18640843
Mus musculus EC50 = 5600.0 nM 5.25 Anticonvulsant activity in mouse by measuring free brain concentration 33859800
Frizzled-8 Kd = 16800.0 nM 4.78 Binding affinity to immobilized mouse C-terminal Rhinovirus 3C cleavage site-fus... 32049522
Sodium channel protein type 9 subunit alpha IC50 = 22000.0 nM 4.66 Blockade of human Nav1.7 channel expressed in HEK293 cells by FRET assay 18243692
ADMET Kd = 24200.0 nM 4.62 Binding affinity to Wistar rat brain lipid by TRANSIL assay 21071520
Hepatocyte EC50 = 26000.0 nM 4.58 Induction of CYP2B6 mRNA expression in human donor hepatocytes after 48 hrs by r... 22815312
Unchecked IC50 = 30000.0 nM 4.52 Inhibition of veratridine-induced guanidine flux in cardiac voltage-gated sodium... 11170622
Sodium channel protein type 9 subunit alpha Ki = 32700.0 nM 4.49 Inhibition of Nav1.7 (unknown origin) by electrophysiological assay 25466191
Nucleic Acid Ki = 46100.0 nM 4.34 Dissociation constant for binding to inactivated state of rat brain NaIIa (rNav1... 15293999
Sodium channel protein type 5 subunit alpha IC50 = 46800.0 nM 4.33 Inhibition of human Nav1.5 at -60 mV holding potential by automated patch-clamp ... 36092147
Sodium channel protein type 4 subunit alpha Ki = 52000.0 nM 4.28 Affinity for inactive human SkM1 sodium channel expressed in HEK293 cells 14998340
Sodium channel protein type 9 subunit alpha IC50 = 91300.0 nM 4.04 Inhibition of human Nav1.7 at -60 mV holding potential by automated patch-clamp ... 36092147

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1442
- 10.6019/CHEMBL3885881 Rattus norvegicus 301
17451232 10.1021/jm061431g Rattus norvegicus 40
20116141 10.1016/j.ejmech.2009.12.077 Mus musculus 20
20416982 10.1016/j.ejmech.2010.03.041 Mus musculus 18
16472241 10.2174/1570163043334794 Hepatotoxicity 18
23085104 10.1016/j.ejmech.2012.08.037 Mus musculus 18
21536355 10.1016/j.ejmech.2011.04.020 Mus musculus 18
- 10.1007/s00044-012-0271-z Mus musculus 15
19272675 10.1016/j.ejmech.2009.02.015 Mus musculus 15
2308142 10.1021/jm00165a007 Mus musculus 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
27597416 10.1016/j.ejmech.2016.08.032 NON-PROTEIN TARGET 12
- 10.1007/s00044-013-0778-y Mus musculus 12
17950496 10.1016/j.ejmech.2007.08.006 Mus musculus 12
23124217 10.1016/j.ejmech.2012.10.002 Mus musculus 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
25740159 10.1016/j.bmcl.2015.02.013 No relevant target 10
27876250 10.1016/j.bmc.2016.11.014 NON-PROTEIN TARGET 10
8831764 10.1021/jm9603025 Mus musculus 9

Data from ChEMBL 36 via Core Engine