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azetukalner   Click here for help

GtoPdb Ligand ID: 12650

Synonyms: 1OP2198 | encukalner (deleted INN) | Example 11 [WO2008024398A2] | VRX621698 | XEN-1101 | XEN1101
PDB Ligand
Compound class: Synthetic organic
Comment: Azetukalner (XEN1101; former INN encukalner) is a clinical stage voltage-gated potassium channel (Kv7) activator [3], that was developed as a potential anti-epileptic drug, or for the treatment of major depressive disorder. It activates Kv7.2 and Kv7.3 channel subtypes.

azetukalner is commercially available from our sponsors

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 3
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 32.34
Molecular weight 368.49
XLogP 3.72
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 CC1=C(C(=CC(=C1)N2CCC3=CC(=CC=C3C2)F)C)NC(=O)CC(C)(C)C
Isomeric SMILES CC1=CC(=CC(=C1NC(=O)CC(C)(C)C)C)N2CCC3=C(C2)C=CC(=C3)F
InChI InChI=1S/C23H29FN2O/c1-15-10-20(11-16(2)22(15)25-21(27)13-23(3,4)5)26-9-8-17-12-19(24)7-6-18(17)14-26/h6-7,10-12H,8-9,13-14H2,1-5H3,(H,25,27)
InChI Key FJNPZKZPWVVSON-UHFFFAOYSA-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. Butterfield NN, Luzon Rosenblut C, Fava M, Correll CU, Rothschild AJ, Murrough JW, Mathew SJ, Beatch GN, Grayson C, Harden C et al.. (2025)
Azetukalner, a Novel KV7 Potassium Channel Opener, in Adults With Major Depressive Disorder: A Randomized Clinical Trial.
JAMA Netw Open, 8 (5): e2514278. [PMID:40423966]
2. French JA, Porter RJ, Perucca E, Brodie MJ, Rogawski MA, Harden C, Qian J, Rosenblut CL, Kenney C, Beatch GN et al.. (2025)
Interim analysis of the long-term efficacy and safety of azetukalner in an ongoing open-label extension study following a phase 2b clinical trial (X-TOLE) in adults with focal epilepsy.
Epilepsia Open, 10 (2): 539-548. [PMID:40053315]
3. Vernier JM, De La Rosa MA, Chen H, Wu JZ, Larson GL, Cheney IW. (2008)
Derivatives of 4-(n-azacycloalkyl) anilides as potassium channel modulators.
Patent number: WO2008024398A2. Assignee: Valeant Pharmaceuticals International. Priority date: 22/08/2007. Publication date: 28/02/2008.