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].
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: retigabine

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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]