cenobamate   Click here for help

GtoPdb Ligand ID: 10773

Synonyms: Ontozry® | Xcopri® | YKP-3089 | YKP3089
Approved drug
cenobamate is an approved drug (FDA (2019), EMA (2021))
Compound class: Synthetic organic
Comment: Cenobamate (YKP-3089) is an oral anti-epilepsy drug. Pharmacological evidence shows that it acts as a positive allosteric modulator (PAM) at GABAA channels [4] and as an inhibitor of the INaP current via voltage-gated sodium channels [3] in isolated rat hippocampal neurons.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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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.

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Physico-chemical Properties
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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.

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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 95.92
Molecular weight 267.05
XLogP 1.6
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
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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/)

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Canonical SMILES NC(=O)O[C@H](c1ccccc1Cl)Cn1nncn1
Isomeric SMILES NC(=O)O[C@H](c1ccccc1Cl)Cn1nncn1
InChI InChI=1S/C10H10ClN5O2/c11-8-4-2-1-3-7(8)9(18-10(12)17)5-16-14-6-13-15-16/h1-4,6,9H,5H2,(H2,12,17)/t9-/m0/s1
InChI Key GFHAXPJGXSQLPT-VIFPVBQESA-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/)
References
1. Keam SJ. (2020)
Cenobamate: First Approval.
Drugs, 80 (1): 73-78. DOI: 10.1007/s40265-019-01250-6 [PMID:31933170]
2. Krauss GL, Klein P, Brandt C, Lee SK, Milanov I, Milovanovic M, Steinhoff BJ, Kamin M. (2020)
Safety and efficacy of adjunctive cenobamate (YKP3089) in patients with uncontrolled focal seizures: a multicentre, double-blind, randomised, placebo-controlled, dose-response trial.
Lancet Neurol, 19 (1): 38-48. DOI: 10.1016/S1474-4422(19)30399-0 [PMID:31734103]
3. Nakamura M, Cho JH, Shin H, Jang IS. (2019)
Effects of cenobamate (YKP3089), a newly developed anti-epileptic drug, on voltage-gated sodium channels in rat hippocampal CA3 neurons.
Eur J Pharmacol, 855: 175-182. [PMID:31063770]
4. Sharma R, Nakamura M, Neupane C, Jeon BH, Shin H, Melnick SM, Glenn KJ, Jang IS, Park JB. (2020)
Positive allosteric modulation of GABAA receptors by a novel antiepileptic drug cenobamate.
Eur J Pharmacol, 879: 173117. [PMID:32325146]