Apixaban

Apixaban

Clinical data
Trade names	Eliquis
License data	EU EMA: Eliquis
Routes of administration	Oral
ATC code	B01AF02 (WHO)
Legal status
Legal status	UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability	~50%
Protein binding	~87%
Metabolism	CYP3A4, CYP3A5, CYP1A2 and others
Biological half-life	9–14 h
Excretion	Biliary (75%), renal (25%)
Identifiers
IUPAC name 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
CAS Number	503612-47-3 Y
PubChem CID	10182969
IUPHAR/BPS	6390
DrugBank	DB07828 Y
ChemSpider	8358471 Y
UNII	3Z9Y7UWC1J
KEGG	D03213 Y
ChEMBL	CHEMBL231779 Y
ECHA InfoCard	100.167.332
Chemical and physical data
Formula	C25H25N5O4
Molar mass	459.497 g/mol
3D model (Jmol)	Interactive image
SMILES O=C5N(c4ccc(N3C(=O)c1c(c(nn1c2ccc(OC)cc2)C(=O)N)CC3)cc4)CCCC5
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) Y Key:QNZCBYKSOIHPEH-UHFFFAOYSA-N Y

Apixaban, sold under the tradename Eliquis, is an anticoagulant for the treatment of venous thromboembolic events. It is taken by mouth. It is a direct factor Xa inhibitor.

Apixaban was approved in Europe in 2012. It was approved in the U.S. in 2014 for treatment and secondary prophylaxis of deep vein thrombosis (DVT) and pulmonary embolism (PE). It is being developed in a joint venture by Pfizer and Bristol-Myers Squibb.

Apixaban is indicated for the following:

Apixaban is recommended by the National Institute for Health and Clinical Excellence for the prevention of stroke and systemic embolism in people with non-valvular atrial fibrillation and at least one of the following risk factors: prior stroke or transient ischemic attack, age 75 years or older, diabetes mellitus, or symptomatic heart failure.

Apixaban and other newer anticoagulants (dabigatran and rivaroxaban) appear equally effective as warfarin in preventing non-hemorrhagic stroke in people with atrial fibrillation and are associated with lower risk of intracranial bleeding.

Premature discontinuation of any oral anticoagulant, including apixaban, increases thrombotic event risk. This is not due to any rebound effect from discontinuation. To reduce this risk, administering another anticoagulant is advised.

Apixaban can increase the risk of bleeding and may cause serious, potentially fatal, bleeding. Concurrent use with drugs affecting hemostasis (e.g. other anticoagulants, heparin, aspirin and other antiplatelet drugs, selective serotonin reuptake inhibitors, serotonin norepinephrine reuptake inhibitors, and nonsteroidal anti-inflammatory drugs (NSAIDs) can further increase the risk of bleeding.