Structure via PubChem · Public domain (PubChem)
ezogabine
Sign in to saveAlso known as AWD-21360, D-23129, Potiga®, Trobalt®, WAY-143841, ethyl {2-amino-4-[(4-fluorobenzyl)amino]phenyl}carbamate, N-(2-Amino-4-(4-fluorobenzylamino)phenyl)carbamic acid ethyl ester, Ethyl 2-amino-4-((p-fluorobenzyl)amino)carbanilate
Retigabine (INN) or ezogabine (USAN) is an anticonvulsant used as an adjunctive treatment for partial epilepsies in treatment-experienced adult patients. The drug was developed by Valeant Pharmaceuticals and GlaxoSmithKline. It was approved by the European Medicines Agency under the trade name Trobalt on March 28, 2011, and by the United States Food and Drug Administration (FDA), under the trade name Potiga, on June 10, 2011. Production was discontinued in June 2017.
Key facts
- Drug.H
- 18
- Drug.F
- 1
- Drug.N
- 3
- Drug.O
- 2
- Drug.image
- Retigabine2DCSD.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 250
- Drug.image2
- Retigabine ball-and-stick model from xtal 2021.png
- Drug.image_class2
- bg-transparent
- Drug.USAN
- ezogabine
- Drug.tradename
- Trobalt, Potiga
- Drug.MedlinePlus
- a612028
- Drug.licence_EU
- yes
- Drug.licence_US
- Ezogabine
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- N03
- Drug.ATC_suffix
- AX21
- Drug.legal_AU
- S4
via Wikipedia infobox
Chemical data
- Formula
- C16H18FN3O2
- Molecular weight
- 303.33 g/mol
- IUPAC name
- ethyl N-[2-amino-4-[(4-fluorophenyl)methylamino]phenyl]carbamate
- SMILES
- CCOC(=O)NC1=C(C=C(C=C1)NCC2=CC=C(C=C2)F)N
- InChIKey
- PCOBBVZJEWWZFR-UHFFFAOYSA-N
- XLogP
- 2.8
- Polar surface area
- 76.4 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2011
- Admin. routes
- oral
- Indications
- epilepsy, Seizure, major depressive disorder, depressive disorder
via ChEMBL · EBI
Research
485 papersvia PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 303.138305
- Has use
- medication
Show 7 more facts
- chemical formula
- C₁₆H₁₈FN₃O₂
- canonical SMILES
- CCOC(=O)NC1=C(C=C(C=C1)NCC2=CC=C(C=C2)F)N
- World Health Organisation international non-proprietary name
- retigabine
- Commons category
- Retigabine
- defined daily dose
- 0.9
- medical condition treated
- epilepsy
- physically interacts with
- Potassium voltage-gated channel subfamily Q member 4
Sources (6)
via Wikidata · CC0
~7 min read
Encyclopedic overview
11 sectionsContents
- Adverse effects
- Interactions
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- History
- Clinical trials
- Regulatory approval
- Name
- References
- Further reading
Retigabine (INN) or ezogabine (USAN) is an anticonvulsant used as an adjunctive treatment for partial epilepsies in treatment-experienced adult patients. The drug was developed by Valeant Pharmaceuticals and GlaxoSmithKline. It was approved by the European Medicines Agency under the trade name Trobalt on March 28, 2011, and by the United States Food and Drug Administration (FDA), under the trade name Potiga, on June 10, 2011. Production was discontinued in June 2017.
Retigabine works primarily as a potassium channel opener—that is, by activating a certain family of voltage-gated potassium channels in the brain. This mechanism of action is unique among antiepileptic drugs, and may hold promise for the treatment of other neurologic conditions, including tinnitus, migraine and neuropathic pain. The manufacturer withdrew retigabine from clinical use in 2017 due to declining use, after the addition of a black box warning regarding side effects was added to the drug in 2013.
Excerpted from Wikipedia’s “ezogabine” article, available under the CC BY-SA 4.0 licence.