Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1407)
Drug Name
Retigabine
Synonyms
Retigabine; Retigabine [INN]; Trobalt; WAY-143841; D-20443; D-23129; Ezogabine; Ezogabine [USAN]; GKE-841; Potiga; 12G01I6BBU; 150812-12-7; C16H18FN3O2; CHEBI:68584; CHEMBL41355; D 20443; D 23129; Ethyl (2-amino-4-(((4-fluorophenyl)methyl)amino)phenyl)carbamate; Ethyl 2-amino-4-((p-fluorobenzyl)amino)carbanilate; N-(2-Amino-4-(4-fluorobenzylamino)phenyl)carbamic acid ethyl ester; UNII-12G01I6BBU; ethyl N-[2-amino-4-[(4-fluorophenyl)methylamino]phenyl]carbamate
Indication Epilepsy [ICD11: 8A60] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 303.33 Topological Polar Surface Area 76.4
Heavy Atom Count 22 Rotatable Bond Count 6
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
121892
PubChem SID
854071 ; 10239851 ; 12015005 ; 14800601 ; 24263039 ; 29302387 ; 49898865 ; 50233601 ; 53788352 ; 57339830 ; 58107328 ; 85174557 ; 85202062 ; 91615883 ; 92715048 ; 103220716 ; 103875964 ; 104032719 ; 104414526 ; 118046799 ; 118855330 ; 124490309 ; 125341609 ; 126623656 ; 126655065 ; 126665918 ; 128896436 ; 131299831 ; 134338628 ; 135077118 ; 135650896 ; 136345679 ; 136920410 ; 136946473 ; 137156938 ; 141970640 ; 152034730 ; 152159608 ; 160645840 ; 162011781 ; 162205078 ; 163123042 ; 163620909 ; 163686230 ; 164042455 ; 164194995 ; 164233343 ; 164786707 ; 174006313 ; 174527464
ChEBI ID
CHEBI:68584
CAS Number
150812-12-7
TTD Drug ID
D0X7GL
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
N-Acetyl Retigabine DM004862
10107340
Conjugation - N-acetylation 1 [4]
Retigabine-N2-glucuronide DM004860
156596533
Conjugation - Glucuronidation 1 [4] , [2] , [3]
Retigabine-N4-glucuronide DM004861 N. A. Conjugation - Glucuronidation 1 [4] , [2] , [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005236 Retigabine Retigabine-N2-glucuronide Conjugation - Glucuronidation UGT1A3 ... [4], [2], [3]
MR005237 Retigabine Retigabine-N4-glucuronide Conjugation - Glucuronidation UGT1A3 ... [4], [2], [3]
MR005238 Retigabine N-Acetyl Retigabine Conjugation - N-acetylation Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME0048 Homo sapiens
UD14_HUMAN
2.4.1.17
[4] , [2] , [3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[2]
References
1 Antibodies and venom peptides: new modalities for ion channels. Nat Rev Drug Discov. 2019 May;18(5):339-357.
2 Retigabine N-glucuronidation and its potential role in enterohepatic circulation. Drug Metab Dispos. 1999 May;27(5):605-12.
3 N-Glucuronidation of the antiepileptic drug retigabine: results from studies with human volunteers, heterologously expressed human UGTs, human liver, kidney, and liver microsomal membranes of Crigler-Najjar type II. Metabolism. 2006 Jun;55(6):711-21.
4 Retigabine: the newer potential antiepileptic drug

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