eslicarbazepine   Click here for help

GtoPdb Ligand ID: 7350

Synonyms: Aptiom® | BIA 2-194 | S-licarbazepine | Zebinix®
Approved drug
eslicarbazepine is an approved drug (FDA (2013))
Compound class: Synthetic organic
Comment: Eslicarbazepine is an anticonvulsant. The PubChem CID for eslicarbazepine acetate is CID 179344.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: eslicarbazepine

eslicarbazepine is commercially available from our sponsors

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 66.56
Molecular weight 254.11
XLogP 1.24
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES OC1Cc2ccccc2N(c2c1cccc2)C(=O)N
Isomeric SMILES O[C@H]1Cc2ccccc2N(c2c1cccc2)C(=O)N
InChI InChI=1S/C15H14N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8,14,18H,9H2,(H2,16,19)/t14-/m0/s1
InChI Key BMPDWHIDQYTSHX-AWEZNQCLSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
The acetate form is a prodrug for eslicarbazepine, and has had European (EMA) approval from 2009 (as Zebinix®), as adjunctive therapy for partial-onset epileptic seizures. In September 2015, the US FDA approved eslicarbazepine as a monotherapy for partial-onset seizures.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
This drug has identical action to oxcarbazepine. The pharmacological activity of oxcarbazepine is thought to be associated with its 10-monohydroxy metabolite (MHD), which acts as a sodium channel inhibitor. This blocks initiation and conductance of nerve impulses. The genes and proteins SNC1A-SNC11A are listed in this database in the Voltage-gated sodium channels section.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)