retigabine   Click here for help

GtoPdb Ligand ID: 2601

Synonyms: AWD-21360 | D-23129 | ezogabine | Potiga® | Trobalt® | WAY-143841
Approved drug PDB Ligand
retigabine is an approved drug (FDA and EMA (2011))
Compound class: Synthetic organic
Comment: Retigabine is unique among antiepileptic drugs in that it functions by activating selected voltage-gated potassium channels in the brain (i.e. Kv7 family channels) [3] [4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 76.38
Molecular weight 303.14
XLogP 2.57
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCOC(=O)Nc1ccc(cc1N)NCc1ccc(cc1)F
Isomeric SMILES CCOC(=O)Nc1ccc(cc1N)NCc1ccc(cc1)F
InChI InChI=1S/C16H18FN3O2/c1-2-22-16(21)20-15-8-7-13(9-14(15)18)19-10-11-3-5-12(17)6-4-11/h3-9,19H,2,10,18H2,1H3,(H,20,21)
InChI Key PCOBBVZJEWWZFR-UHFFFAOYSA-N
References
1. Dupuis DS, Schrøder RL, Jespersen T, Christensen JK, Christophersen P, Jensen BS, Olesen SP. (2002)
Activation of KCNQ5 channels stably expressed in HEK293 cells by BMS-204352.
Eur J Pharmacol, 437 (3): 129-37. [PMID:11890900]
2. Liu R, Tzounopoulos T, Wipf P. (2019)
Synthesis and Optimization of Kv7 (KCNQ) Potassium Channel Agonists: The Role of Fluorines in Potency and Selectivity.
ACS Med Chem Lett, 10 (6): 929-935. DOI: 10.1021/acsmedchemlett.9b00097 [PMID:31223450]
3. Main MJ, Cryan JE, Dupere JR, Cox B, Clare JJ, Burbidge SA. (2000)
Modulation of KCNQ2/3 potassium channels by the novel anticonvulsant retigabine.
Mol Pharmacol, 58 (2): 253-62. [PMID:10908292]
4. Rogawski MA, Bazil CW. (2008)
New molecular targets for antiepileptic drugs: alpha(2)delta, SV2A, and K(v)7/KCNQ/M potassium channels.
Curr Neurol Neurosci Rep, 8 (4): 345-52. [PMID:18590620]
5. Tatulian L, Delmas P, Abogadie FC, Brown DA. (2001)
Activation of expressed KCNQ potassium currents and native neuronal M-type potassium currents by the anti-convulsant drug retigabine.
J Neurosci, 21 (15): 5535-45. [PMID:11466425]
6. Wainger BJ, Macklin EA, Vucic S, McIlduff CE, Paganoni S, Maragakis NJ, Bedlack R, Goyal NA, Rutkove SB, Lange DJ et al.. (2021)
Effect of Ezogabine on Cortical and Spinal Motor Neuron Excitability in Amyotrophic Lateral Sclerosis: A Randomized Clinical Trial.
JAMA Neurol, 78 (2): 186-196. [PMID:33226425]