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
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)
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.
External links Click here for help