apixaban   Click here for help

GtoPdb Ligand ID: 6390

Synonyms: BMS-562247 | Eliquis®
Approved drug PDB Ligand
apixaban is an approved drug (EMA (2011), FDA (2012))
Compound class: Synthetic organic
Comment: Apixaban belongs to the direct factor Xa inhibitor family of drugs, which also includes rivaroxaban and edoxaban.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 110.24
Molecular weight 459.19
XLogP 1.81
No. Lipinski's rules broken 0
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Canonical SMILES COc1ccc(cc1)n1nc(c2c1C(=O)N(CC2)c1ccc(cc1)N1CCCCC1=O)C(=O)N
Isomeric SMILES COc1ccc(cc1)n1nc(c2c1C(=O)N(CC2)c1ccc(cc1)N1CCCCC1=O)C(=O)N
InChI 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)
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Summary of Clinical Use Click here for help
Direct factor Xa inhibitor for treatment of venous thromboembolism, such as that experienced following hip or knee replacement surgery, or clots in the brain or other organs. In August 2014 the US FDA granted additional approval for this drug to be used to both treat, and reduce the risk of recurrent deep vein thrombosis (DVT) and pulmonary embolism (PE).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
This family of drugs inhibits coagulation without using antithrombin as a mediator. They are competitive inhibitors of free and clot bound factor Xa, which blocks the amplification of the coagulation cascade, preventing thrombus formation.
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