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

General Information of Drug (ID: DR0913)
Drug Name
Lamotrigine
Synonyms
Lamictal; Lamictal Cd; Lamictal ODT; Lamictal XR; Lamotrigina; Lamotrigina [Spanish]; Lamotrigine, 98%; Lamotriginum; Lamotriginum [Latin]; PYZRQGJRPPTADH-UHFFFAOYSA-N; U3H27498KS; lamotrigine; 1,2,4-Triazine-3,5-diamine, 6-(2,3-dichlorophenyl)-; 3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine; 3,5-Diamino-6-(2,3-dichlorophenyl)-as-triazine; 6-(2,3-Dichlorophenyl)-1,2,4-triazine-3,5-diamine; 84057-84-1; BW 430C; BW-430C; C9H7Cl2N5; CHEBI:6367; CHEMBL741; EINECS 281-901-8; GW 273293; MFCD00865333; MLS000069685; UNII-U3H27498KS
Indication Bipolar disorder [ICD11: 6A60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 256.089 Topological Polar Surface Area 90.7
Heavy Atom Count 16 Rotatable Bond Count 1
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
3878
PubChem SID
855818 ; 5669156 ; 7847420 ; 7979720 ; 8152444 ; 11111377 ; 11113342 ; 11528749 ; 12013463 ; 14823602 ; 17405249 ; 24278792 ; 26719658 ; 29222992 ; 46386680 ; 46505408 ; 47810853 ; 48259345 ; 48416154 ; 50100261 ; 50104089 ; 50104090 ; 53777794 ; 53787568 ; 56423136 ; 57322032 ; 58107296 ; 76843584 ; 81092819 ; 85231112 ; 90341162 ; 91148150 ; 92304062 ; 92308151 ; 92308280 ; 92308924 ; 92709766 ; 93166952 ; 103199382 ; 103940000 ; 104179107 ; 104304778 ; 111978157 ; 117872151 ; 121361621 ; 124658861 ; 124799528 ; 124880544 ; 124880545 ; 124880546
ChEBI ID
CHEBI:6367
CAS Number
84057-84-1
TTD Drug ID
D03FLC
Formula
C9H7Cl2N5
Canonical SMILES
C1=CC(=C(C(=C1)Cl)Cl)C2=C(N=C(N=N2)N)N
InChI
1S/C9H7Cl2N5/c10-5-3-1-2-4(6(5)11)7-8(12)14-9(13)16-15-7/h1-3H,(H4,12,13,14,16)
InChIKey
PYZRQGJRPPTADH-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
Lamivudine-2-N-methyl metabolite DM000206 N. A. Unclear 1 [5] , [6] , [7]
Lamotrigine-2-N-glucuronide DM000204
164342
Conjugation - Glucuronidation 1 [5] , [6] , [7]
Lamotrigine-5-N-glucuronide DM000205 N. A. Conjugation - Glucuronidation 1 [5] , [4] , [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001410 Lamotrigine Lamotrigine-2-N-glucuronide Conjugation - Glucuronidation UGT1A3 ... [5], [6], [7]
MR001411 Lamotrigine Lamotrigine-5-N-glucuronide Conjugation - Glucuronidation UGT1A3 ... [5], [4], [7]
MR001412 Lamotrigine Lamivudine-2-N-methyl metabolite Unclear Unclear [5], [6], [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME0048 Homo sapiens
UD14_HUMAN
2.4.1.17
[4]
References
1 Lamotrigine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8.
3 Variation in glucuronidation of lamotrigine in human liver microsomes. Xenobiotica. 2009 May;39(5):355-63.
4 Studies on induction of lamotrigine metabolism in transgenic UGT1 mice. Xenobiotica. 2009 Nov;39(11):826-35.
5 Pharmacokinetics, toxicology and safety of lamotrigine in epilepsy Expert Opin Drug Metab Toxicol. 2006 Dec;2(6):1009-18. doi: 10.1517/17425255.2.6.1009.
6 Simultaneous determination of plasma lamotrigine, lamotrigine N2-glucuronide and lamotrigine N2-oxide by UHPLC-MS/MS in epileptic patients. J Pharm Biomed Anal. 2022 Oct 25;220:115017. doi: 10.1016/j.jpba.2022.115017.
7 UDP-glucuronosyltransferase 1A4-mediated N2-glucuronidation is the major metabolic pathway of lamotrigine in chimeric NOG-TKm30 mice with humanised-livers. Xenobiotica. 2021 Oct;51(10):1146-1154. doi: 10.1080/00498254.2021.1972492.

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