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

General Information of Drug (ID: DR1431)
Drug Name
Rivaroxaban
Synonyms
Rivaroxaban; Rivaroxaban (Xarelto); Rivaroxaban, 98%; Xarelto; (S)-5-Chloro-N-((2-oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)thiophene-2-carboxamide; 2-Thiophenecarboxamide, 5-chloro-N-[[(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-; 366789-02-8; Q-102503; 5-Chloro-N-({(5s)-2-Oxo-3-[4-(3-Oxomorpholin-4-Yl)phenyl]-1,3-Oxazolidin-5-Yl}methyl)thiophene-2-Carboxamide; 9NDF7JZ4M3; BAY 59-7939; BAY-59-7939; BAY59-7939; CHEBI:68579; UNII-9NDF7JZ4M3
Indication Deep vein thrombosis [ICD11: BD71] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 435.9 Topological Polar Surface Area 116
Heavy Atom Count 29 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
9875401
PubChem SID
14856850 ; 15279667 ; 22395270 ; 24164597 ; 45622373 ; 46513422 ; 51091428 ; 52936629 ; 56373953 ; 57373622 ; 71825413 ; 87225360 ; 87557471 ; 91615930 ; 93580340 ; 99444948 ; 103469795 ; 109693118 ; 126659499 ; 126666963 ; 134342998 ; 134358083 ; 135213418 ; 135684125 ; 136375511 ; 136920411 ; 137128738 ; 139479843 ; 152258851 ; 152344334 ; 160645892 ; 160647701 ; 160969514 ; 162172236 ; 164045359 ; 164194090 ; 164824489 ; 165245531 ; 170498903 ; 171578894 ; 172091286 ; 174477515 ; 175266472 ; 175427064 ; 175610897 ; 177748765 ; 178103004 ; 180189087 ; 185985285 ; 198991713
ChEBI ID
ChEBI:68579
CAS Number
366789-02-8
TTD Drug ID
D0KG3R
Formula
C19H18ClN3O5S
Canonical SMILES
C1COCC(=O)N1C2=CC=C(C=C2)N3CC(OC3=O)CNC(=O)C4=CC=C(S4)Cl
InChI
1S/C19H18ClN3O5S/c20-16-6-5-15(29-16)18(25)21-9-14-10-23(19(26)28-14)13-3-1-12(2-4-13)22-7-8-27-11-17(22)24/h1-6,14H,7-11H2,(H,21,25)/t14-/m0/s1
InChIKey
KGFYHTZWPPHNLQ-AWEZNQCLSA-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
Rivaroxaban M15 DM015752
11346837
Unclear - Unclear 1 [4]
Rivaroxaban M2 DM016583
131667831
Other reaction - Hydoxylation 1 [4]
Rivaroxaban M3 DM016584
131667832
Other reaction - Hydoxylation 1 [4]
Rivaroxaban M5 DM016117
46782891
Unclear - Unclear 1 [4]
Rivaroxaban M6 DM016212
59190906
Unclear - Unclear 1 [4]
Rivaroxaban M7 DM017917 N. A. Unclear - Unclear 1 [4]
Rivaroxaban M8 DM016869
166708110
Other reaction - Hydoxylation 1 [4]
Rivaroxaban M9 DM016426
92021096
Other reaction - Hydoxylation 1 [4]
Rivaroxaban M1 DM016423
91971681
Unclear - Unclear 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009553 Rivaroxaban Rivaroxaban M2 Other reaction - Hydoxylation Unclear [4]
MR009555 Rivaroxaban Rivaroxaban M3 Other reaction - Hydoxylation Unclear [4]
MR009556 Rivaroxaban Rivaroxaban M5 Unclear - Unclear Unclear [4]
MR009557 Rivaroxaban Rivaroxaban M6 Unclear - Unclear Unclear [4]
MR009558 Rivaroxaban Rivaroxaban M7 Unclear - Unclear Unclear [4]
MR009559 Rivaroxaban Rivaroxaban M8 Other reaction - Hydoxylation Unclear [4]
MR009560 Rivaroxaban Rivaroxaban M9 Other reaction - Hydoxylation Unclear [4]
MR009561 Rivaroxaban Rivaroxaban M15 Unclear - Unclear Unclear [4]
MR009554 Rivaroxaban M2 Rivaroxaban M1 Unclear - Unclear Unclear [4]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2J2 (CYP2J2) DME0031 Homo sapiens
CP2J2_HUMAN
1.14.14.24
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
References
1 Rivaroxaban was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Comparative efficacy and safety of the novel oral anticoagulants dabigatran, rivaroxaban and apixaban in preclinical and clinical development. Thromb Haemost. 2010 Mar;103(3):572-85.
3 Pharmacology of the new target-specific oral anticoagulants. J Thromb Thrombolysis. 2013 Aug;36(2):133-40.
4 Metabolism and excretion of rivaroxaban, an oral, direct factor Xa inhibitor, in rats, dogs, and humans

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