rivaroxaban   Click here for help

GtoPdb Ligand ID: 6388

Synonyms: BAY 59-7939 | Xarelto®
Approved drug PDB Ligand
rivaroxaban is an approved drug (EMA (2008), FDA (2011))
Compound class: Synthetic organic
Comment: First in class orally active direct factor Xa inhibitor.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 116.42
Molecular weight 435.07
XLogP 0.61
No. Lipinski's rules broken 0
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Canonical SMILES O=C1OC(CN1c1ccc(cc1)N1CCOCC1=O)CNC(=O)c1ccc(s1)Cl
Isomeric SMILES O=C1O[C@H](CN1c1ccc(cc1)N1CCOCC1=O)CNC(=O)c1ccc(s1)Cl
InChI 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
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Summary of Clinical Use Click here for help
Factor Xa inhibitor for the prevention of venous thromboembolic events. In October 2018 the FDA expanded approval to permit the use of rivaroxaban in patients living with chronic coronary or peripheral artery disease (CAD/PAD), who are at serious risk of suffering a myocardial infarction or stroke [1-2].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Competitive inhibitor of free and clot bound factor Xa, which blocks the amplification of the coagulation cascade, preventing thrombus formation. This family of drugs inhibits coagulation without using antithrombin as a mediator.
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