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

General Information of Drug (ID: DR0624)
Drug Name
Eslicarbazepine acetate
Prodrug Info Eslicarbazepine acetate is the prodrug of Eslicarbazepine
Synonyms
Eslicarbazepine (acetate); Eslicarbazepine acetate; Eslicarbazepine acetate (USAN); Eslicarbazepine acetate [USAN]; Exalief; SEP-0002093; Sep 0002093; Stedesa; UNII-BEA68ZVB2K; Zebinix; [(5S)-11-carbamoyl-5,6-dihydrobenzo[b][1]benzazepin-5-yl] acetate; Exelief; (S)-(-)-10-Acetoxy-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide; (S)-5-Carbamoyl-10,11-dihydro-5H-dibenzo[b,f]azepin-10-yl acetate; 236395-14-5; Aptiom; BEA68ZVB2K; BIA 2-093; BIA 2093; BIA-2-093; CHEBI:87016; CHEMBL87992
Indication Epilepsy [ICD11: 8A60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 296.32 Topological Polar Surface Area 72.6
Heavy Atom Count 22 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
179344
ChEBI ID
CHEBI:87016
CAS Number
236395-14-5
TTD Drug ID
D04QZD
Formula
C17H16N2O3
Canonical SMILES
CC(=O)OC1CC2=CC=CC=C2N(C3=CC=CC=C13)C(=O)N
InChI
1S/C17H16N2O3/c1-11(20)22-16-10-12-6-2-4-8-14(12)19(17(18)21)15-9-5-3-7-13(15)16/h2-9,16H,10H2,1H3,(H2,18,21)/t16-/m0/s1
InChIKey
QIALRBLEEWJACW-INIZCTEOSA-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
Eslicarbazepine DM002012
9881504
Unclear 1 [5]
Eslicarbazepine-O-glucuronide metabolite DM002017 N. A. Unclear 2 [5] , [6]
Oxcarbazepine DM002013
34312
Oxidation - Oxidation 2 [5] , [6]
10-hydroxycarbazepine glucuronide metabolite DM002014 N. A. Unclear 3 [7]
Eslicarbazepine DM002012
9881504
Reduction - Reduction 3 [7]
Oxcarbazepine alcohol sulfate DM001113
146675081
Unclear 3 [7]
R-licarbazepine DM002016
9816485
Reduction - Reduction 3 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000946 Eslicarbazepine acetate Eslicarbazepine Unclear Unclear [5]
MR000944 Eslicarbazepine Oxcarbazepine Oxidation - Oxidation Unclear [5], [6]
MR000945 Eslicarbazepine Eslicarbazepine-O-glucuronide metabolite Unclear UGT1A1 [5], [6]
MR000947 Oxcarbazepine Oxcarbazepine alcohol sulfate Unclear Unclear [7]
MR000948 Oxcarbazepine Eslicarbazepine Reduction - Reduction ES [7]
MR000949 Oxcarbazepine 10-hydroxycarbazepine glucuronide metabolite Unclear Unclear [7]
MR000950 Oxcarbazepine R-licarbazepine Reduction - Reduction Unclear [7]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Arylacetamide deacetylase (AADAC) DMEN272 Homo sapiens
AAAD_HUMAN
3.1.1.3
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME0048 Homo sapiens
UD14_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 2B17 (UGT2B17) DME0066 Homo sapiens
UDB17_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 2B4 (UGT2B4) DME0047 Homo sapiens
UD2B4_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[5]
⏷ Show the Full List of 8  DME(s)
References
1 Eslicarbazepine Acetate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Role of Human Arylacetamide Deacetylase (AADAC) on Hydrolysis of Eslicarbazepine Acetate and Effects of AADAC Genetic Polymorphisms on Hydrolase Activity
3 Hepatic UDP-glucuronosyltransferase is responsible for eslicarbazepine glucuronidation. Drug Metab Dispos. 2011 Sep;39(9):1486-94.
4 DrugBank(Pharmacology-Metabolism):Eslicarbazepine acetate
5 Pharmacokinetics and drug interactions of eslicarbazepine acetate Epilepsia. 2012 Jun;53(6):935-46. doi: 10.1111/j.1528-1167.2012.03519.x.
6 Key factors in the discovery and development of new antiepileptic drugs Nat Rev Drug Discov. 2010 Jan;9(1):68-82. doi: 10.1038/nrd2997.
7 U. S. FDA Label -Eslicarbazepine acetate

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