retigabine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
gabamimetic agents 4181 150812-12-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • D-20443
  • trobalt
  • ezogabine
  • potiga
  • KE 841
  • GW 582892X
  • WAY 143841
  • retigabine
In vitro studies indicate that ezogabine enhances transmembrane potassium currents mediated by the KCNQ (Kv7.2 to 7.5) family of ion channels. By activating KCNQ channels, ezogabine is thought to stabilize the resting membrane potential and reduce brain excitability.
  • Molecular weight: 303.34
  • Formula: C16H18FN3O2
  • CLOGP: 2
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 3
  • TPSA: 76.38
  • ALOGS: -3.99
  • ROTB: 6

  • Status: OFM

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.90 g O

ADMET properties:

PropertyValueReference
Vd (Volume of distribution) 2.50 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 8.30 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.20 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 9 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
March 28, 2011 EMA
June 10, 2011 FDA GLAXOSMITHKLINE

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Retinal pigmentation 111.64 47.52 12 441 30 46685579
Seizure 59.15 47.52 27 426 123027 46562582
Epilepsy 56.67 47.52 17 436 23721 46661888
Status epilepticus 55.97 47.52 15 438 13964 46671645
Urinary retention 55.10 47.52 17 436 26044 46659565

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Retinal pigmentation 139.31 63.35 14 276 12 29952176
Seizure 68.90 63.35 28 262 98447 29853741

Pharmacologic Action:

SourceCodeDescription
ATC N03AX21 NERVOUS SYSTEM
ANTIEPILEPTICS
ANTIEPILEPTICS
Other antiepileptics
MeSH PA D000927 Anticonvulsants
MeSH PA D002491 Central Nervous System Agents
MeSH PA D049990 Membrane Transport Modulators
FDA MoA N0000182728 Potassium Channel Openers
FDA EPC N0000182729 Potassium Channel Opener
CHEBI has role CHEBI:35623 antiepileptic

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Partial Epilepsy Treatment Adjunct indication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.53 acidic
pKa2 4.74 Basic
pKa3 3.12 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Potassium voltage-gated channel subfamily KQT member 2 Ion channel ACTIVATOR EC50 5.60 IUPHAR CHEMBL
Potassium voltage-gated channel subfamily KQT member 4 Ion channel ACTIVATOR EC50 5.20 IUPHAR CHEMBL
Potassium voltage-gated channel subfamily KQT member 5 Ion channel ACTIVATOR EC50 5 IUPHAR CHEMBL
Potassium voltage-gated channel subfamily KQT member 3 Ion channel ACTIVATOR EC50 6.20 IUPHAR CHEMBL
Potassium voltage-gated channel subfamily KQT member 2 Ion channel EC50 5.89 CHEMBL

External reference:

IDSource
4030907 VUID
N0000182972 NUI
D09569 KEGG_DRUG
4030907 VANDF
C0384053 UMLSCUI
CHEBI:68584 CHEBI
FBX PDB_CHEM_ID
CHEMBL41355 ChEMBL_ID
DB04953 DRUGBANK_ID
C101866 MESH_SUPPLEMENTAL_RECORD_UI
121892 PUBCHEM_CID
2601 IUPHAR_LIGAND_ID
7545 INN_ID
12G01I6BBU UNII
1112990 RXNORM
184560 MMSL
27995 MMSL
d07769 MMSL
013807 NDDF
699271005 SNOMEDCT_US
704476003 SNOMEDCT_US

Pharmaceutical products:

None