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

General Information of Drug (ID: DR0558)
Drug Name
Edoxaban
Synonyms
Edoxaban (USAN/INN); Edoxaban [USAN:INN]; Edoxaban hydrochloride; HGVDHZBSSITLCT-JLJPHGGASA-N; Lixiana; NDU3J18APO; PB31142; DU-176; DU-176b; EDOXABAN; SAVAYSA; SCHEMBL330046; ZINC43200832; 480449-70-5; 912273-65-5; ACN-039922; AKOS005146069; AOB87348; BDBM50328731; C24H30ClN7O4S; CHEBI:85973; CHEMBL1269025; DTXSID50197398; GTPL7575; KS-000004VY; MFCD13195544; N1-(5-chloropyridin-2-yl)-N2-((1S,2R,4S)-4-(dimethylcarbamoyl)-2-(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamido)cyclohexyl)oxalamide; UNII-NDU3J18APO
Indication Atrial fibrillation [ICD11: BC81] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 548.1 Topological Polar Surface Area 165
Heavy Atom Count 37 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
10280735
PubChem SID
15285745 ; 22657909 ; 35552742 ; 75383420 ; 109693269 ; 123092995 ; 123107846 ; 124490450 ; 135263753 ; 141477305 ; 152343994 ; 162198449 ; 163409416 ; 163620696 ; 163686010 ; 163909302 ; 170502825 ; 172096222 ; 172121849 ; 185988955 ; 198981897 ; 198992538 ; 223365911 ; 223397933 ; 223922733 ; 226666786 ; 249273064 ; 249736672 ; 249865853 ; 252090008 ; 252150280 ; 252451702 ; 252552142
ChEBI ID
CHEBI:85973
CAS Number
912273-65-5
TTD Drug ID
D0C3BS
Formula
C24H30ClN7O4S
Canonical SMILES
CN1CCC2=C(C1)SC(=N2)C(=O)NC3CC(CCC3NC(=O)C(=O)NC4=NC=C(C=C4)Cl)C(=O)N(C)C
InChI
1S/C24H30ClN7O4S/c1-31(2)24(36)13-4-6-15(27-20(33)21(34)30-19-7-5-14(25)11-26-19)17(10-13)28-22(35)23-29-16-8-9-32(3)12-18(16)37-23/h5,7,11,13,15,17H,4,6,8-10,12H2,1-3H3,(H,27,33)(H,28,35)(H,26,30,34)/t13-,15-,17+/m0/s1
InChIKey
HGVDHZBSSITLCT-JLJPHGGASA-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
Edoxaban metabolite M1 DM000561
59676792
Unclear 1 [2]
Edoxaban metabolite M2 DM019994
59677038
Unclear 1 [2]
Edoxaban metabolite M3 DM019995 N. A. Unclear 1 [2]
Edoxaban metabolite M4 DM000560
59676899
Hydrolysis - Hydrolysis 1 [2]
Edoxaban metabolite M5 DM019993 N. A. Unclear 1 [2]
Edoxaban metabolite M6 DM000562
16661115
Unclear 1 [2]
Edoxaban metabolite M7 DM019992
155543712
Unclear 1 [2]
Edoxaban metabolite M8 DM000563
59676785
Unclear 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003447 Edoxaban Edoxaban metabolite M7 Unclear CYP3A4 ... [2]
MR003449 Edoxaban Edoxaban metabolite M6 Unclear CYP3A4 ... [2]
MR003450 Edoxaban Edoxaban metabolite M5 Unclear CYP3A4 ... [2]
MR003451 Edoxaban Edoxaban metabolite M1 Unclear Unclear [2]
MR003452 Edoxaban Edoxaban metabolite M2 Unclear Unclear [2]
MR003453 Edoxaban Edoxaban metabolite M3 Unclear Unclear [2]
MR003454 Edoxaban Edoxaban metabolite M4 Hydrolysis - Hydrolysis CES1 [2]
MR003448 Edoxaban metabolite M7 Edoxaban metabolite M8 Unclear Unclear [2]
⏷ 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
Carboxylesterase 1 (CES1) DME0054 Homo sapiens
EST1_HUMAN
3.1.1.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
References
1 Edoxaban was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Pharmacokinetics, biotransformation, and mass balance of edoxaban, a selective, direct factor Xa inhibitor, in humans Drug Metab Dispos. 2012 Dec;40(12):2250-5. doi: 10.1124/dmd.112.046888.
3 Edoxaban drug-drug interactions with ketoconazole, erythromycin, and cyclosporine. Br J Clin Pharmacol. 2016 Dec;82(6):1591-1600.

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