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

General Information of Drug (ID: DR1744)
Drug Name
Oxcarbazepine
Prodrug Info Oxcarbazepine is the prodrug of Eslicarbazepine
Synonyms
Oxcarbamazepine; Oxcarbazepina; Oxcarbazepina [INN-Spanish]; Oxcarbazepinum; Oxcarbazepinum [INN-Latin]; Trileptal; 10,11-Dihydro-10-oxo-5H-dibenz(b,f)azepine-5-carboxamide; 10,11-Dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxamide; GP 47680; GP-47680; KIN-493; OXCARBAZEPINE; 10-Oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide; 28721-07-5; 5-oxo-6H-benzo[b][1]benzazepine-11-carboxamide; 5H-Dibenz[b,f]azepine-5-carboxamide, 10,11-dihydro-10-oxo-; EINECS 249-188-8; MFCD00865307; MLS000084586; UNII-VZI5B1W380
Indication Epilepsy [ICD11: 8A60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 252.27 Topological Polar Surface Area 63.4
Heavy Atom Count 19 Rotatable Bond Count 0
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
34312
PubChem SID
9695 ; 866068 ; 866523 ; 7784956 ; 7847599 ; 7980216 ; 8173559 ; 11364569 ; 11367131 ; 11369693 ; 11372776 ; 11374387 ; 11377855 ; 11484081 ; 11488299 ; 11491484 ; 11492449 ; 11495489 ; 11528646 ; 12013820 ; 15196775 ; 24724563 ; 26612687 ; 26679796 ; 26719673 ; 26747194 ; 26747195 ; 34676003 ; 46386767 ; 46507580 ; 47291388 ; 47365462 ; 50085868 ; 50105170 ; 53790510 ; 57311661 ; 75522661 ; 81040908 ; 81093135 ; 87561105 ; 92124721 ; 92307920 ; 92308514 ; 92309109 ; 92711414 ; 93166236 ; 96099912 ; 99233256 ; 99437127 ; 103292787
ChEBI ID
CHEBI:7824
CAS Number
28721-07-5
TTD Drug ID
D0QL3P
Formula
C15H12N2O2
Canonical SMILES
C1C2=CC=CC=C2N(C3=CC=CC=C3C1=O)C(=O)N
InChI
1S/C15H12N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8H,9H2,(H2,16,19)
InChIKey
CTRLABGOLIVAIY-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
Eslicarbazepine DM002012
9881504
Reduction - Reduction 1 [3]
Oxcarbazepine alcohol sulfate DM001113
146675081
Conjugation - Sulfation 1 [4]
Oxcarbazepine glucuronide DM001114
71316174
Conjugation - O-Glucuronidation 1 [4]
R-licarbazepine DM002016
9816485
Reduction - Reduction 1 [3]
10,11-Dihydroxycarbamazepine DM000723
83852
Oxidation - Oxidation 2 [5]
Cis-10,11-Dihydroxy-10,11-dihydrocarbamazepine DM001109
13726065
Oxidation - Oxidation 2 [5]
R-Licarbazepine glucuronide DM001108
71750797
Conjugation - O-Glucuronidation 2 [5]
S-Licarbazepine glucuronide DM001112 N. A. Conjugation - O-Glucuronidation 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001869 Oxcarbazepine Oxcarbazepine alcohol sulfate Conjugation - Sulfation Unclear [4]
MR001870 Oxcarbazepine Oxcarbazepine glucuronide Conjugation - O-Glucuronidation Unclear [4]
MR001871 Oxcarbazepine Eslicarbazepine Reduction - Reduction AKR1C1 ... [3]
MR001872 Oxcarbazepine R-licarbazepine Reduction - Reduction AKR1C1 ... [3]
MR001865 R-licarbazepine R-Licarbazepine glucuronide Conjugation - O-Glucuronidation Unclear [5]
MR001866 R-licarbazepine Cis-10,11-Dihydroxy-10,11-dihydrocarbamazepine Oxidation - Oxidation Unclear [5]
MR001867 R-licarbazepine Trans-10,11-dihydro-10,11-dihydroxycarbamazepine Oxidation - Oxidation Unclear [5]
MR001868 R-licarbazepine S-Licarbazepine glucuronide Conjugation - O-Glucuronidation Unclear [5]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [2]
References
1 Oxcarbazepine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
3 The role of carbonyl reducing enzymes in oxcarbazepine in vitro metabolism in man. Chem Biol Interact. 2014 Sep 5;220:241-7.
4 The metabolism of 14C-oxcarbazepine in man Xenobiotica. 1986 Aug;16(8):769-78. doi: 10.3109/00498258609043567.
5 DrugBank(Pharmacology-Metabolism)Oxcarbazepine

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