CHEBI:68584 - ezogabine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name ezogabine
ChEBI ID CHEBI:68584
Definition A substituted aniline that is benzene-1,2,4-triamine bearing ethoxycarbonyl and 4-fluorobenzyl substituents at positions N-1 and N-4 respectively. An anticonvulsant used to treat seizures associated with epilepsy in adults.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB6192082, ChemicalBook:CB5854419, eMolecules:475094, ZINC000000056434
Download Molfile XML SDF
Wikipedia License
Bisphenol A (BPA) is a chemical compound primarily used in the manufacturing of various plastics. It is a colourless solid which is soluble in most common organic solvents, but has very poor solubility in water. BPA is produced on an industrial scale by the condensation reaction of phenol and acetone. Global production in 2022 was estimated to be in the region of 10 million tonnes. BPA's largest single application is as a co-monomer in the production of polycarbonates, which accounts for 65–70% of all BPA production. The manufacturing of epoxy resins and vinyl ester resins account for 25–30% of BPA use. The remaining 5% is used as a major component of several high-performance plastics, and as a minor additive in PVC, polyurethane, thermal paper, and several other materials. It is not a plasticizer, although it is often wrongly labelled as such. The health effects of BPA have been the subject of prolonged public and scientific debate. BPA is a xenoestrogen, exhibiting hormone-like properties that mimic the effects of estrogen in the body. Although the effect is very weak, the pervasiveness of BPA-containing materials raises concerns, as exposure is effectively lifelong. Many BPA-containing materials are non-obvious but commonly encountered, and include coatings for the inside of food cans, clothing designs, shop receipts, and dental fillings. BPA has been investigated by public health agencies in many countries, as well as by the World Health Organization. While normal exposure is below the level currently associated with risk, several jurisdictions have taken steps to reduce exposure on a precautionary basis, in particular by banning BPA from baby bottles. There is some evidence that BPA exposure in infants has decreased as a result of this. BPA-free plastics have also been introduced, which are manufactured using alternative bisphenols such as bisphenol S and bisphenol F, but there is also controversy around whether these are actually safer.
Read full article at Wikipedia
Formula C16H18FN3O2
Net Charge 0
Average Mass 303.33140
Monoisotopic Mass 303.13830
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)
InChIKey PCOBBVZJEWWZFR-UHFFFAOYSA-N
SMILES CCOC(=O)Nc1ccc(NCc2ccc(F)cc2)cc1N
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): potassium channel modulator

Application(s): anticonvulsant
A drug used to prevent seizures or reduce their severity.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ezogabine (CHEBI:68584) has functional parent benzene-1,2,4-triamine (CHEBI:29148)
ezogabine (CHEBI:68584) has role anticonvulsant (CHEBI:35623)
ezogabine (CHEBI:68584) has role potassium channel modulator (CHEBI:50510)
ezogabine (CHEBI:68584) is a carbamate ester (CHEBI:23003)
ezogabine (CHEBI:68584) is a organofluorine compound (CHEBI:37143)
ezogabine (CHEBI:68584) is a secondary amino compound (CHEBI:50995)
ezogabine (CHEBI:68584) is a substituted aniline (CHEBI:48975)
INN Source
retigabine KEGG DRUG
Synonyms Sources
D-23129 ChemIDplus
D-23129 KEGG COMPOUND
Ethyl 2-amino-4-((p-fluorobenzyl)amino)carbanilate ChemIDplus
ethyl {2-amino-4-[(4-fluorobenzyl)amino]phenyl}carbamate ChEBI
N-(2-Amino-4-(4-fluorobenzylamino)-phenyl) carbamic acid ethyl ester KEGG COMPOUND
N-(2-Amino-4-(4-fluorobenzylamino)phenyl)carbamic acid ethyl ester ChemIDplus
Brand Name Source
Potiga KEGG DRUG
Manual Xrefs Databases
4181 DrugCentral
C13826 KEGG COMPOUND
D09569 KEGG DRUG
Ezogabine Wikipedia
US2002015730 Patent
US2002111379 Patent
US2002183395 Patent
US2012053238 Patent
US5384330 Patent
US6348486 Patent
WO2007090409 Patent
WO2011012659 Patent
View more database links
Registry Numbers Types Sources
150812-12-7 CAS Registry Number KEGG COMPOUND
150812-12-7 CAS Registry Number ChemIDplus
8072099 Reaxys Registry Number Reaxys
Citation Type Source
22991134 PubMed citation Europe PMC
Last Modified
22 February 2017