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

General Information of Drug (ID: DR0122)
Drug Name
Apixaban
Synonyms
Apixaban; Apixaban(BMS-562247-01); Eliquis; apixabanum; 1-(4-Methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide; 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide; 3Z9Y7UWC1J; 503612-47-3; BMS 562247-01; BMS-562247; BMS-562247-01; BMS562247-01; CHEBI:72296; CHEMBL231779; UNII-3Z9Y7UWC1J
Indication Deep vein thrombosis [ICD11: BD71] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 459.5 Topological Polar Surface Area 111
Heavy Atom Count 34 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
10182969
PubChem SID
15178464 ; 17397366 ; 22578033 ; 26736936 ; 40272539 ; 46519072 ; 51992439 ; 53812906 ; 56310620 ; 57374335 ; 99375349 ; 99444299 ; 103535612 ; 104253239 ; 109693404 ; 124757362 ; 124772059 ; 125164166 ; 125433570 ; 126644898 ; 126665798 ; 134339057 ; 135252374 ; 135727449 ; 135727826 ; 136367462 ; 136368094 ; 136920385 ; 137183704 ; 139455355 ; 144115617 ; 152258806 ; 152343992 ; 152344098 ; 160647657 ; 160874191 ; 160962913 ; 160968889 ; 162011738 ; 163884621 ; 164194092 ; 164777207 ; 165247616 ; 170497908 ; 172912849 ; 174006823 ; 174549337 ; 175266926 ; 175427077 ; 178103006
ChEBI ID
CHEBI:72296
CAS Number
503612-47-3
TTD Drug ID
D0I5HF
Formula
C25H25N5O4
Canonical SMILES
COC1=CC=C(C=C1)N2C3=C(CCN(C3=O)C4=CC=C(C=C4)N5CCCCC5=O)C(=N2)C(=O)N
InChI
1S/C25H25N5O4/c1-34-19-11-9-18(10-12-19)30-23-20(22(27-30)24(26)32)13-15-29(25(23)33)17-7-5-16(6-8-17)28-14-3-2-4-21(28)31/h5-12H,2-4,13-15H2,1H3,(H2,26,32)
InChIKey
QNZCBYKSOIHPEH-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
Apixaban M2 metabolite DM000611
10203943
Oxidation - O-Demethylation 1 [2] , [5]
Apixaban M4/7 metabolite DM000615 N. A. Oxidation - Hydroxylation 1 [2] , [5]
Apixaban M1 metabolite DM000614
91667715
Conjugation - Sulfation 2 [6] , [7]
Apixaban M13 metabolite DM000612 N. A. Oxidation - Hydroxylation 2 [7]
Apixaban M10 metabolite DM000613 N. A. Conjugation - Sulfation 3 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000248 Apixaban Apixaban M2 metabolite Oxidation - O-Demethylation CYP1A2 ... [2], [5]
MR000249 Apixaban Apixaban M4/7 metabolite Oxidation - Hydroxylation CYP1A2 ... [2], [5]
MR000244 Apixaban M2 metabolite Apixaban M13 metabolite Oxidation - Hydroxylation Unclear [7]
MR000245 Apixaban M2 metabolite Apixaban M1 metabolite Conjugation - Sulfation SULT1A1 [6], [7]
MR000247 Apixaban M4/7 metabolite Apixaban M13 metabolite Oxidation - Hydroxylation Unclear [7]
MR000246 Apixaban M13 metabolite Apixaban M10 metabolite Conjugation - Sulfation Unclear [7]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2J2 (CYP2J2) DME0031 Homo sapiens
CP2J2_HUMAN
1.14.14.24
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[5]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
Sulfotransferase 1A1 (SULT1A1) DME0008 Homo sapiens
ST1A1_HUMAN
2.8.2.1
[6]
⏷ Show the Full List of 8  DME(s)
References
1 Apixaban was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Apixaban. Hosp Pharm. 2013 Jun;48(6):494-509.
3 Apixaban Hosp Pharm. 2013 Jun;48(6):494-509. doi: 10.1310/hpj4806-494.
4 In vitro assessment of metabolic drug-drug interaction potential of apixaban through cytochrome P450 phenotyping, inhibition, and induction studies. Drug Metab Dispos. 2010 Mar;38(3):448-58.
5 Apixaban. After hip or knee replacement: LMWH remains the standard treatment. Prescrire Int. 2012 Sep;21(130):201-2, 204.
6 Sulfation of o-demethyl apixaban: enzyme identification and species comparison. Drug Metab Dispos. 2009 Apr;37(4):802-8. doi: 10.1124/dmd.108.025593.
7 Apixaban metabolism and pharmacokinetics after oral administration to humans Drug Metab Dispos. 2009 Jan;37(1):74-81. doi: 10.1124/dmd.108.023143.

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