General
Preferred name
APIXABAN
Synonyms
BMS-562247-01 ()
Eliquis ()
Apixaban (BMS 562247-01) ()
BMS 562247-01 ()
BMS-562247 ()
Apixaban-13C-d3 ()
P&D ID
PD009294
CAS
503612-47-3
1261393-15-0
Tags
natural product
drug
available
Approved by
EMA
FDA
First approval
2012
2011
Drug Status
approved
Drug indication
Thrombosis
Max Phase
Phase 4
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
ABSORPTION
Apixaban is approximately 50% bioavailable[Label] though other studies report 43-46% oral bioavailability[A177565].
ROE
56% of an orally administered dose is recovered in the feces and 24.5-28.8% of the dose is recovered in the urine[label,A177565,A6897]. 83-88% of the dose recovered in the urine was the unchanged parent compound[A177565].
PHARMACODYNAMICS
Apixaban selectively inhibits factor Xa in its free and bound forms, independant of antithrombin III[Label]. Apixaban also inhibits prothrominase[Label]. These effects prevent the formation of a thrombus[Label].
INDICATION
Apixaban is indicated for reducing the risk of stroke and systemic embolism in patients who have nonvalvular atrial fibrillation, prophylaxis of deep vein thrombosis(DVT) leading to pulmonary embolism(PE) in patients after a hip or knee replacement surgery, and treatment of DVT and PE to reduce the risk of recurrence[Label,A177565,A6897].
HALF-LIFE
12.7±8.55h[Label,A177565,A6897].
METABOLISM
50% of the orally administered dose is excreted as the unchanged parent compound, however 25% of the dose is excreted as O-demethyl apixaban sulfate[Label,A177565]. All apixaban metabolites account for approximately 32% of the excreted dose though the structure of all metabolites are not well defined[A177565]. Apixaban is mainly metabolized by cytochrome p450(CYP)3A4 and to a lesser extent by CYP1A2, CYP2C8, CYP2C9, CYP2C19, and CYP2J2[Label].
DESCRIPTION
Apixaban belongs to the direct factor Xa inhibitor family of drugs, which also includes and .
(GtoPdb)
TOXICITY
Animal studies have shown an increased risk of maternal bleeding during pregnancy but no increase in fetal malformations or fetal or maternal deaths[Label]. It is unknown if this animal data also translates to humans so apixaban should only be used in pregnancy if the benefits outweigh the risks[Label]. It is not know whether apixaban is safe and effective in labor and during birth, though animal studies have shown an increased rate of maternal bleeding[Label]. Animal studies in rats show apixaban excreted in milk, though it is not know if this also applies to humans[Label]. Nursing mothers should either stop breastfeeding or stop taking apixaban depending on the risk and benefit of each option[Label]. Studies to determine safety and effectiveness in pediatric patients have yet to be performed[Label]. Studies that involved geriatric patients (at least 75 years old) saw no difference in safety or effectiveness compared to younger patients, though geriatric patients at an especially advanced age may be more susceptible to adverse effects[Label]. Dosage adjustments for patients with end stage renal disease(ESRD) are based on estimates of pharmacokinetic principles and not clinical study[Label]. Patients with ESRD may experience pharmacodynamics similar to those seen in well controlled studies but it may not lead to the same clinical effects[Label]. Dosage adjustments are not necessary in mild hepatic impairment[Label]. In moderate hepatic impairment patients may already experience abnormalities in coagulation and so no dose recommendations are possible[Label]. Apixaban is not recommended for patients with severe hepatic impairment[Label].
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
0
Organisms
2
Compound Sets
28
AdooQ Bioactive Compound Library
Axon Medchem Screening Library
ChEMBL Approved Drugs
ChEMBL Drugs
Concise Guide to Pharmacology 2017/18
Concise Guide to Pharmacology 2019/20
Concise Guide to Pharmacology 2021/22
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
Guide to Pharmacology
LSP-MoA library (Laboratory of Systems Pharmacology)
Mcule NIBR MoA Box Subset
MedChem Express Bioactive Compound Library
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
Novartis Chemogenetic Library (NIBR MoA Box)
ReFrame library
Selleckchem Bioactive Compound Library
TargetMol Bioactive Compound Library
The Spectrum Collection
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
41
Molecular Weight
459.19
Hydrogen Bond Acceptors
6
Hydrogen Bond Donors
1
Rotatable Bonds
5
Ring Count
5
Aromatic Ring Count
3
cLogP
2.7
TPSA
110.76
Fraction CSP3
0.28
Chiral centers
0.0
Largest ring
6.0
QED
0.63
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
Metabolism
Metabolic Enzyme/Protease
Target
Factor Xa (human)
Factor Xa (rabbit)
F10
Factor Xa inhibitor
Factor Xa
Member status
virtual
MOA
Known FactorXa inhibitor
coagulation factor inhibitor
Indication
stroke, systemic embolism, pulmonary embolism (PE), atrial fibrillation (AF), deep vein thrombosis (DVT)
Disease Area
neurology/psychiatry, hematology, cardiology
Biosynthetic Origin
Peptide (Ribosomal)
Therapeutic Indication
Anticoagulant
Therapeutic Class
Cardiovascular
Source data
