carbamazepine   Click here for help

GtoPdb Ligand ID: 5339

Synonyms: calepsin | Carnexiv® | Tegretol®
Approved drug PDB Ligand
carbamazepine is an approved drug (FDA (1968))
Compound class: Synthetic organic
Comment: Carbamazepine is a tricyclic anticonvulsant.
Carbamazepine has been shown to inhibit Wnt/β-catenin signalling by binding to an allosteric site of the Wnt ligand receptor FZD8 [4]. It does not bind to FZD5 so can be used to distinguish between these two receptors.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 46.33
Molecular weight 236.09
XLogP 2.3
No. Lipinski's rules broken 0
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Canonical SMILES NC(=O)N1c2ccccc2C=Cc2c1cccc2
Isomeric SMILES NC(=O)N1c2ccccc2C=Cc2c1cccc2
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)
No information available.
Summary of Clinical Use Click here for help
Carbamazepine is used to treat seizures and nerve pain such as trigeminal neuralgia and diabetic neuropathy. It is also used to treat bipolar disorder.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The mechanism of action of carbamazepine is complex and poorly defined, but appears to involve inhibition of sodium channel α subunits. Information published in early 2020 suggests that carbamazepine acts as an allosteric inhibitor of Wnt activation of the FZD8 receptor [4], and that this may contribute to its anti-epileptic action, since dysregulation of Wnt/β-catenin signalling has been linked with the development of temporal lobe epilepsy [1-3].