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
No information available.
Summary of Clinical Use Click here for help
Retigabine was approved to treat intractable partial-onset epileptic seizures. Use of retigabine was discontinued in 2017 due to serious side-effects including urinary retention, blue skin, and retinal discoloration. The poor selectivity of retigabine among Kv7.2-Kv7.5 channels, and issues around its metabolic degradation products are considered to contribute to these adverse events. Channel activators with improved selectivity for Kv7.2/Kv7.3 are being developed and investigated [2].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Retigabine acts as a neuronal voltage activated potassium channel opener but may also affect inhibitory GABA neurotransmission by the GABAA receptor. See the DrugBank link for further details.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02450552 Clinical Trial of Ezogabine (Retigabine) in ALS Subjects Phase 2 Interventional Massachusetts General Hospital 6
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