Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00263)
Name
Ezogabine
Synonyms    Click to Show/Hide the Synonyms of This API
Retigabine; Ezogabine; 150812-12-7; Potiga; D-23129; Trobalt; N-(2-Amino-4-(4-fluorobenzylamino)phenyl)carbamic acid ethyl ester; GKE-841; Ethyl 2-amino-4-((p-fluorobenzyl)amino)carbanilate; UNII-12G01I6BBU; Ezogabine [USAN]; WAY-143841; ethyl N-[2-amino-4-[(4-fluorophenyl)methylamino]phenyl]carbamate; D 20443; D-20443; N-(2-Amino-4-(4-fluorobenzylamino)-phenyl) carbamic acid ethyl ester; CHEMBL41355; 12G01I6BBU; CHEBI:68584; Ethyl (2-amino-4-(((4-fluorophenyl)methyl)amino)phenyl)carbamate; Retigabine (INN); Retigabine [INN]; Ezogabine (USAN); AWD-21360; AWD21-360; GW582892X; MFCD04307735; GW-582892X; ethyl {2-amino-4-[(4-fluorobenzyl)amino]phenyl}carbamate; 2-AMINO-4-(4-FLUORBENZYLAMINO)-1-ETHOXYCARBONYLAMINOBENZENE; Ethyl [2-amino-4-[[(4-fluorophenyl)methyl]amino]phenyl]carbamate; ethyl N-[2-azanyl-4-[(4-fluorophenyl)methylamino]phenyl]carbamate; [2-Amino-4-(4-fluoro-benzylamino)-phenyl]-carbamic acid ethyl ester; Retigabin; Potiva; D 23129; GW 582892X; WAY 143841; Trobalt, Potiga; HSDB 8171; GKI 841; N03AX21; Potiga (TN); ADD-230001; KE-0201; Trobalt, Potiga,Retigabine; Carbamic acid, (2-amino-4-(((4-fluorophenyl)methyl)amino)phenyl)-, ethyl ester; SCHEMBL20835; cc-439; Retigabine, analytical standard; GTPL2601; DEA No. 2779; Retigabine, >=98% (HPLC); ZINC16154; DTXSID40164615; [2-Amino-4-[[(4-fluorophenyl)methyl]amino]phenyl]-carbamate; HMS3748I09; HMS3885L20; BCP04194; EX-A2203; N-(2-amino-4-[fluorobenzylamino]-phenyl) carbamic acid; D-23129; Retigabine,D2312, D-23129; BDBM50143558; ZINC00016154; AKOS015895311; AC-6908; CCG-267503; CS-0990; DB04953; QC-1587; NCGC00346739-01; NCGC00346739-05; NCGC00346739-06; AW21-360; HY-15471; BCP0726000089; AB0035830; FT-0601527; C13826; D09569; S-7700; 812R127; A809076; Q-101418; Q2146170; ethyl 2-amino-4-(4-fluorobenzylamino)phenylcarbamate; ethyl N-(2-amino-4-{[(4-fluorophenyl)methyl]amino}phenyl)carbamate; N-(2-amino-4-(4-fluorobenzylamino)-phenyl)carbamic acid ethylester; N-[2-amino-4-[(4-fluorophenyl)methylamino]phenyl]carbamic acid ethyl ester; Retigabine solution, 1.0 mg/mL in acetonitrile, ampule of 1 mL, certified reference material
Clinical Status
Approved
Disease Indication Epilepsy ICD-11: 8A60 [1]
PubChem CID
121892
Formula
C16H18FN3O2
Canonical SMILES
CCOC(=O)NC1=C(C=C(C=C1)NCC2=CC=C(C=C2)F)N
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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=121892"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 303.33 Topological Polar Surface Area 76.4
XlogP 2.8 Complexity 348
Heavy Atom Count 22 Rotatable Bond Count 6
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Full List of Drug Formulations (DFMs) Containing This API
          Ezogabine 400 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Cochineal; Fd&c blue no. 2; Magnesium stearate; Talc; Titanium dioxide; Croscarmellose sodium; Lecithin, soybean; Polyvinyl alcohol; Cellulose, microcrystalline; Hypromelloses; Xanthan gum
                   Dosage Form Oral Tablet
                   Company GlaxoSmithKline
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Caprylic acid DIG Info GPCR84 receptor (Ki = 19600 nM) [3]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
Soybean lecithin DIG Info Albendazole monooxygenase (IC50 = 6.61 mg.mL-1) [6]
          Ezogabine 50 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Cochineal; Fd&c blue no. 2; Magnesium stearate; Talc; Titanium dioxide; Croscarmellose sodium; Lecithin, soybean; Polyvinyl alcohol; Cellulose, microcrystalline; Hypromelloses; Xanthan gum
                   Dosage Form Oral Tablet
                   Company GlaxoSmithKline
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Caprylic acid DIG Info GPCR84 receptor (Ki = 19600 nM) [3]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
Soybean lecithin DIG Info Albendazole monooxygenase (IC50 = 6.61 mg.mL-1) [6]
          Ezogabine 300 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Fd&c blue no. 2; Magnesium stearate; Ferric oxide yellow; Talc; Titanium dioxide; Croscarmellose sodium; Lecithin, soybean; Polyvinyl alcohol; Cellulose, microcrystalline; Hypromelloses; Xanthan gum
                   Dosage Form Oral Tablet
                   Company GlaxoSmithKline
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
Soybean lecithin DIG Info Albendazole monooxygenase (IC50 = 6.61 mg.mL-1) [6]
          Ezogabine 200 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium stearate; Ferric oxide yellow; Talc; Titanium dioxide; Croscarmellose sodium; Lecithin, soybean; Polyvinyl alcohol; Cellulose, microcrystalline; Hypromelloses; Xanthan gum
                   Dosage Form Oral Tablet
                   Company GlaxoSmithKline
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
Soybean lecithin DIG Info Albendazole monooxygenase (IC50 = 6.61 mg.mL-1) [6]
References
1 FDA label for approved ezogabine from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights. J Med Chem. 2020 Mar 12; 63(5):2391-2410.
4 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
5 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
6 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

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