Identification

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Name
Apixaban
Accession Number
DB06605  (DB07828)
Type
Small Molecule
Groups
Approved
Description

Apixaban is an oral, direct, and highly selective factor Xa (FXa) inhibitor of both free and bound FXa, as well as prothrombinase, independent of antithrombin III for the prevention and treatment of thromboembolic diseasesLabel,2. It is marketed under the name EliquisLabel,3. Apixaban was approved by the FDA on December 28, 20123.

Structure
Thumb
Synonyms
  • apixabán
  • Apixaban
  • apixabanum
External IDs
BMS 562247-01 / BMS-562247 / BMS-562247-01
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EliquisTablet5 mgOralBristol Myers Squibb2012-12-21Not applicableCanada
EliquisTablet, film coated2.5 mgOralBristol Myers Squibb / Pfizer Eeig2011-05-18Not applicableEu
EliquisTablet, film coated2.5 mg/1OralE.R. Squibb & Sons, L.L.C.2012-12-28Not applicableUs00003 0893 21 nlmimage10 4048a055
EliquisTablet, film coated2.5 mg/1OralA-S Medication Solutions2012-12-28Not applicableUs50090 143620180907 15195 t6wamc
EliquisTablet, film coated5 mgOralBristol Myers Squibb / Pfizer Eeig2011-05-18Not applicableEu
EliquisTablet, film coated2.5 mgOralBristol Myers Squibb / Pfizer Eeig2011-05-18Not applicableEu
EliquisTablet2.5 mgOralBristol Myers Squibb2012-02-01Not applicableCanada
EliquisTablet, film coated5 mg/1OralREMEDYREPACK INC.2019-02-08Not applicableUs
EliquisTablet, film coated2.5 mgOralBristol Myers Squibb / Pfizer Eeig2011-05-18Not applicableEu
EliquisTablet, film coated5 mgOralBristol Myers Squibb / Pfizer Eeig2011-05-18Not applicableEu
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ELIQUIS 30-Day Starter PackApixaban (5 mg/1) + Apixaban (5 mg/1)OralE.R. Squibb & Sons, L.L.C.2017-11-29Not applicableUs
ELIQUIS 30-Day Starter PackApixaban (5 mg/1) + Apixaban (5 mg/1)OralE.R. Squibb & Sons, L.L.C.2017-11-29Not applicableUs
Categories
UNII
3Z9Y7UWC1J
CAS number
503612-47-3
Weight
Average: 459.4971
Monoisotopic: 459.190654313
Chemical Formula
C25H25N5O4
InChI Key
QNZCBYKSOIHPEH-UHFFFAOYSA-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)
IUPAC Name
1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-1H,4H,5H,6H,7H-pyrazolo[3,4-c]pyridine-3-carboxamide
SMILES
COC1=CC=C(C=C1)N1N=C(C(N)=O)C2=C1C(=O)N(CC2)C1=CC=C(C=C1)N1CCCCC1=O

Pharmacology

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 recurrenceLabel,1,2.

Associated Conditions
Pharmacodynamics

Apixaban selectively inhibits factor Xa in its free and bound forms, independant of antithrombin IIILabel. Apixaban also inhibits prothrominaseLabel. These effects prevent the formation of a thrombusLabel.

Mechanism of action

Apixaban selectively inhibits factor Xa in its free and bound forms, independant of antithrombin IIILabel. Apixaban also inhibits prothrominaseLabel. These effects prevent the formation of a thrombusLabel.

TargetActionsOrganism
ACoagulation factor X
inhibitor
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Apixaban is approximately 50% bioavailableLabel though other studies report 43-46% oral bioavailability1.

Volume of distribution

Approximately 21LLabel.

Protein binding

92-94%Label.

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 sulfateLabel,1. All apixaban metabolites account for approximately 32% of the excreted dose though the structure of all metabolites are not well defined1. Apixaban is mainly metabolized by cytochrome p450(CYP)3A4 and to a lesser extent by CYP1A2, CYP2C8, CYP2C9, CYP2C19, and CYP2J2Label.

Route of elimination

56% of an orally administered dose is recovered in the feces and 24.5-28.8% of the dose is recovered in the urineLabel,1,2. 83-88% of the dose recovered in the urine was the unchanged parent compound1.

Half life

12.7±8.55hLabel,1,2.

Clearance

3.3L/hLabel though other studies report 4876mL/h1.

Toxicity

Animal studies have shown an increased risk of maternal bleeding during pregnancy but no increase in fetal malformations or fetal or maternal deathsLabel. It is unknown if this animal data also translates to humans so apixaban should only be used in pregnancy if the benefits outweigh the risksLabel. 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 bleedingLabel. Animal studies in rats show apixaban excreted in milk, though it is not know if this also applies to humansLabel. Nursing mothers should either stop breastfeeding or stop taking apixaban depending on the risk and benefit of each optionLabel. Studies to determine safety and effectiveness in pediatric patients have yet to be performedLabel. 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 effectsLabel. Dosage adjustments for patients with end stage renal disease(ESRD) are based on estimates of pharmacokinetic principles and not clinical studyLabel. Patients with ESRD may experience pharmacodynamics similar to those seen in well controlled studies but it may not lead to the same clinical effectsLabel. Dosage adjustments are not necessary in mild hepatic impairmentLabel. In moderate hepatic impairment patients may already experience abnormalities in coagulation and so no dose recommendations are possibleLabel. Apixaban is not recommended for patients with severe hepatic impairmentLabel.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(1,2,6,7-3H)Testosterone(1,2,6,7-3H)Testosterone may increase the anticoagulant activities of Apixaban.
(R)-warfarinApixaban may increase the anticoagulant activities of (R)-warfarin.
(S)-WarfarinApixaban may increase the anticoagulant activities of (S)-Warfarin.
1-Testosterone1-Testosterone may increase the anticoagulant activities of Apixaban.
18-methyl-19-nortestosterone18-methyl-19-nortestosterone may increase the anticoagulant activities of Apixaban.
3,5-Diiodotyrosine3,5-Diiodotyrosine may increase the anticoagulant activities of Apixaban.
4-hydroxycoumarinApixaban may increase the anticoagulant activities of 4-hydroxycoumarin.
4-Hydroxytestosterone4-Hydroxytestosterone may increase the anticoagulant activities of Apixaban.
5beta-dihydrotestosterone5beta-dihydrotestosterone may increase the anticoagulant activities of Apixaban.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of bleeding and hemorrhage can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Apixaban.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

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Food Interactions
  • Avoid grapefruit products.
  • Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include alfalfa, anise, and bilberry.
  • Avoid St. John's Wort. St. John's Wort will decrease levels of this medication.

References

General References
  1. Raghavan N, Frost CE, Yu Z, He K, Zhang H, Humphreys WG, Pinto D, Chen S, Bonacorsi S, Wong PC, Zhang D: Apixaban metabolism and pharmacokinetics after oral administration to humans. Drug Metab Dispos. 2009 Jan;37(1):74-81. doi: 10.1124/dmd.108.023143. Epub 2008 Oct 2. [PubMed:18832478]
  2. Granger CB, Alexander JH, McMurray JJ, Lopes RD, Hylek EM, Hanna M, Al-Khalidi HR, Ansell J, Atar D, Avezum A, Bahit MC, Diaz R, Easton JD, Ezekowitz JA, Flaker G, Garcia D, Geraldes M, Gersh BJ, Golitsyn S, Goto S, Hermosillo AG, Hohnloser SH, Horowitz J, Mohan P, Jansky P, Lewis BS, Lopez-Sendon JL, Pais P, Parkhomenko A, Verheugt FW, Zhu J, Wallentin L: Apixaban versus warfarin in patients with atrial fibrillation. N Engl J Med. 2011 Sep 15;365(11):981-92. doi: 10.1056/NEJMoa1107039. Epub 2011 Aug 27. [PubMed:21870978]
  3. FDA Drug Approval Package: Apixaban [Link]
External Links
KEGG Drug
D03213
PubChem Compound
10182969
PubChem Substance
175427077
ChemSpider
8358471
BindingDB
19023
ChEBI
72296
ChEMBL
CHEMBL231779
ZINC
ZINC000011677837
PharmGKB
PA166163740
HET
GG2
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Apixaban
ATC Codes
B01AF02 — Apixaban
AHFS Codes
  • 20:12.04.14 — Direct Factor Xa Inhibitors
PDB Entries
2p16
FDA label
Download (926 KB)
MSDS
Download (52.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingPreventionColorectal Disorders / Crohn's Disease (CD) / Inflammatory Bowel Diseases (IBD) / Pulmonary Embolism / Ulcerative Colitis / Venous Thromboembolism1
1CompletedNot AvailableEnd Stage Renal Disease (ESRD)1
1CompletedNot AvailableThrombotic events1
1CompletedBasic ScienceAnticoagulation1
1CompletedBasic ScienceHealthy Volunteers3
1CompletedBasic ScienceHealthy Volunteers / Pharmacokinetics / Venous Thromboembolism1
1CompletedBasic ScienceN/A - Healthy Subjects2
1CompletedBasic ScienceVenous Thromboembolism1
1CompletedBasic ScienceThrombotic events1
1CompletedOtherNephrotic Syndrome / Proteinuria1
1CompletedTreatmentAcute Coronary Syndromes (ACS) / Atrial Fibrillation (AF)1
1CompletedTreatmentBleeding1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentThrombotic events1
1Not Yet RecruitingOtherPeritoneal dialysis therapy / Renal Insufficiency,Chronic1
1Not Yet RecruitingTreatmentDeep Vein Thrombosis / Malignant Neoplasm of Pancreas / Pulmonary Embolism1
1RecruitingOtherHealthy Volunteers1
1RecruitingOtherThromboembolism1
1RecruitingTreatmentCombination of Oral Anticoagulation Therapy and Sildenafil / Intermediate-high Risk / Pulmonary Embolism1
1TerminatedOtherVenous Thromboembolism1
2Active Not RecruitingTreatmentVenous Thromboembolism1
2CompletedPreventionAcute Coronary Syndromes (ACS)1
2CompletedPreventionKnee Arthroplasty, Total1
2CompletedPreventionMalignancies / Pulmonary Embolism / Thrombotic events1
2CompletedPreventionMalignancies / Venous Thromboembolism1
2CompletedPreventionVTE Prophylaxis With Anticoagulation After Total Knee Replacement Surgery1
2CompletedTreatmentAnticoagulant Toxicity / ESRD1
2CompletedTreatmentAtrial Fibrillation (AF)1
2CompletedTreatmentBleeding1
2CompletedTreatmentDeep Vein Thrombosis1
2CompletedTreatmentHealthy Volunteers1
2Not Yet RecruitingPreventionAtrial Fibrillation (AF)1
2Not Yet RecruitingPreventionEssential Thrombocythemia (ET) / JAK2 Mutation / Myeloproliferative Neoplasms / Polycythemia Vera (PV) / Primary Myelofibrosis / Venous Thromboembolism1
2Not Yet RecruitingTreatmentAnticoagulant-induced Bleeding1
2Not Yet RecruitingTreatmentAtrial Fibrillation (AF)1
2RecruitingPreventionAnti-Xa Activity1
2RecruitingPreventionGynecologic Cancers / Venous Thromboembolism1
2RecruitingPreventionSpinal Cord Injuries (SCI) / Venous Thromboembolism1
2RecruitingTreatmentAmpulla of Vater Cancer / Biliary Cancer (Cholangiocarcinoma, Gall Bladder Cancer) / Cancer-associated Thrombosis / Duodenal Cancer / Esophageal Cancers / Esophagogastric Junction Cancer / Hepatobiliary Cancers / Hepatocellular,Carcinoma / Malignant Gastrointestinal Stromal Tumor / Malignant Neoplasm of Pancreas / Malignant Neoplasm of Stomach1
2RecruitingTreatmentAtrial Fibrillation (AF) / Cerebral Hemorrhage1
2RecruitingTreatmentAtrial Fibrillation (AF) / End Stage Renal Failure on Dialysis1
2RecruitingTreatmentCardiac surgery, heparin-induced thrombocytopenia and thrombosis syndrome / Heparin-induced Thrombocytopenia and Thrombosis1
2RecruitingTreatmentVenous Thromboembolism1
2RecruitingTreatmentThrombotic events1
2TerminatedTreatmentAcute Coronary Syndromes (ACS)1
2WithdrawnNot AvailableAtrial Fibrillation (AF)1
2WithdrawnBasic ScienceAtrial Fibrillation (AF)1
2WithdrawnPreventionCardiac Implantable Electronic Device / Patent Foramen Ovale (PFO)1
2, 3CompletedPreventionCoronary Artery Bypass Graft Surgery Patients / Deep Venous Thrombosis / Postoperative Atrial Fibrilation / Stroke / Systemic Embolism1
2, 3CompletedPreventionPulmonary Embolism / Thrombosis, Venous1
2, 3RecruitingTreatmentMenstruation / Venous Thromboembolism1
2, 3Unknown StatusTreatmentStroke, Ischemic / Transient Ischaemic Attack (TIA)1
3Active Not RecruitingTreatmentVenous Thromboembolism1
3CompletedPreventionAtrial Fibrillation (AF)1
3CompletedPreventionAtrial Fibrillation (AF) / Flutter, Atrial1
3CompletedPreventionAtrial Fibrillation (AF) / Stroke / Transient Ischaemic Attack (TIA)1
3CompletedPreventionAtrial Septal Aneurysm / Migraine / Patent Foramen Ovale (PFO) / Stroke, Ischemic1
3CompletedPreventionDeep Vein Thrombosis / Pulmonary Embolism1
3CompletedPreventionPulmonary Embolism / Thrombosis, Venous1
3CompletedSupportive CareCerebral Vein Thrombosis / Deep Vein Thrombosis / Gonadal Thrombosis / Hepatic Thrombosis / Mesenteric Thrombosis / Metastatic Malignant Neoplasm / Neoplasms, Malignant / Portal Vein Thrombosis / Pulmonary Embolism / Renal Vein Thrombosis / Splenic thrombosis / Venous Thromboembolism1
3CompletedTreatmentDeep Vein Thrombosis / Pulmonary Embolism2
3CompletedTreatmentThrombosis, Venous2
3CompletedTreatmentHematomas1
3Not Yet RecruitingPreventionAtrial Fibrillation (AF) / Cerebral Hemorrhage1
3Not Yet RecruitingPreventionStroke, Ischemic1
3Not Yet RecruitingTreatmentAcute Myocardial Infarction (AMI) / Anticoagulants and Bleeding Disorders / Left Ventricular Thrombosis1
3Not Yet RecruitingTreatmentAortic Valve Disorder / Aortic Valve Failure / Aortic Valve Stenosis1
3RecruitingOtherAtrial Fibrillation (AF)1
3RecruitingPreventionAcute Lymphoblastic Leukaemias (ALL) / Malignant Lymphomas1
3RecruitingPreventionAtrial Fibrillation (AF) / Cerebral Hemorrhage1
3RecruitingPreventionAtrial Fibrillation (AF) / Cerebral Hemorrhage / Microhaemorrhage1
3RecruitingPreventionAtrial Fibrillation (AF) / Flutter, Atrial / Intracranial Hemorrhage, Hypertensive / Intracranial Hemorrhages / Intraventricular Hemorrhage / Microhaemorrhage / Small Vessel Cerebrovascular Disease / Subarachnoid Hemorrhage / Subdural haematoma1
3RecruitingPreventionAtrial Fibrillation (AF) / Stroke1
3RecruitingPreventionCerebral Vein Thrombosis / Deep Vein Thrombosis / Metastatic Malignant Neoplasm / Neoplasms, Malignant / Pulmonary Embolism / Splanchnic Vein Thrombosis1
3RecruitingPreventionIntrahepatic Non Cirrhotic Portal Hypertension1
3RecruitingPreventionStroke1
3RecruitingTreatmentAtrial Fibrillation (AF) / End-Stage Kidney Disease1
3RecruitingTreatmentCancer-associated Thrombosis1
3RecruitingTreatmentCritical Limb Ischemia (CLI)1
3RecruitingTreatmentEligible for Transcatheter Aortic Valve Replacement / Symptomatic Aortic Stenosis1
3RecruitingTreatmentEmbolic Stroke / Embolic Stroke of Undetermined Source1
3RecruitingTreatmentLeft Ventricular Thrombosis1
3RecruitingTreatmentPlasma Cell Myeloma / Venous Thromboembolism1
3RecruitingTreatmentImpaired kidney function1
3TerminatedPreventionAcute Coronary Syndromes (ACS)1
3TerminatedPreventionReduction in Hospitalizations / Sickle Cell Disorders / Vaso-occlusive Crisis1
4Active Not RecruitingPreventionAntiphospholipid Syndrome / Thrombotic events1
4CompletedNot AvailableEnd-Stage Renal Disease (ESRD) / ESRD1
4CompletedOtherAcute Coronary Syndromes (ACS)1
4CompletedOtherNon-valvular Atrial Fibrillation (NVAF)1
4CompletedPreventionAtrial Fibrillation (AF)1
4CompletedPreventionMultiple Myeloma (MM) / Venous Thromboembolism1
4CompletedSupportive CareAtrial Fibrillation (AF)1
4CompletedTreatmentAnticoagulation1
4CompletedTreatmentAtrial Fibrillation (AF)3
4CompletedTreatmentAtrial Fibrillation (AF) / End Stage Renal Disease (ESRD)1
4CompletedTreatmentNeoplasms / Thrombosis, Venous1
4CompletedTreatmentVenous Thromboembolism1
4Not Yet RecruitingTreatmentAORTIC VALVE DISEASES / Thromboembolism1
4Not Yet RecruitingTreatmentAnticoagulants and Bleeding Disorders / Foot Ankle Injuries / Venous Thromboembolism1
4Not Yet RecruitingTreatmentAtrial Fibrillation (AF)1
4Not Yet RecruitingTreatmentAtrial Fibrillation (AF) / Ischemic Heart Disease1
4Not Yet RecruitingTreatmentDeep Vein Thrombosis / Pulmonary Embolism / Venous Thromboembolism1
4Not Yet RecruitingTreatmentPulmonary Embolism / Pulmonary Embolism Subacute Massive / Pulmonary Embolism With Acute Cor Pulmonale / Pulmonary Embolism With Pulmonary Infarction / Right Ventricular Dysfunction / Right Ventricular Failure1
4RecruitingBasic ScienceBMI >30 kg/m2 / Post-gastrointestinal bypass surgery1
4RecruitingOtherLung Transplant / Pharmacokinetics / Transplant, Kidney1
4RecruitingPreventionAnticoagulants / Venous Thromboembolism1
4RecruitingPreventionAtrial Fibrillation (AF)2
4RecruitingPreventionAtrial Fibrillation (AF) / Stroke1
4RecruitingPreventionBleeding / Left Atrial Appendage Closure / Stroke / Thrombotic events / Transient Ischaemic Attack (TIA)1
4RecruitingTreatmentAtrial Fibrillation (AF)1
4RecruitingTreatmentDeep Vein Thrombosis1
4RecruitingTreatmentDeep Vein Thrombosis / Deep Venous Thrombosis / Thromboembolism / Upper Extremity Deep Venous Thrombosis / Venous Thromboembolism1
4RecruitingTreatmentDeep Vein Thrombosis / Pulmonary Embolism1
4RecruitingTreatmentDiabetes1
4RecruitingTreatmentVenous Thromboembolism2
4TerminatedPreventionVentricular Tachycardia (VT)1
4TerminatedTreatmentVenous Thromboembolism1
Not AvailableActive Not RecruitingNot AvailableAnticoagulation1
Not AvailableActive Not RecruitingNot AvailableAtrial Fibrillation (AF)3
Not AvailableActive Not RecruitingNot AvailableNon-valvular Atrial Fibrillation (NVAF)1
Not AvailableActive Not RecruitingNot AvailableNonvalvular Atrial Fibrillation1
Not AvailableActive Not RecruitingNot AvailableVenous Thromboembolism1
Not AvailableActive Not RecruitingHealth Services ResearchNeoplasms / Thrombosis, Venous1
Not AvailableCompletedNot AvailableAnticoagulation2
Not AvailableCompletedNot AvailableAtrial Fibrillation (AF)10
Not AvailableCompletedNot AvailableAtrial Fibrillation (AF) / Death / Major Bleeding / Myocardial Infarction / Stroke, Ischemic / Systemic Embolization2
Not AvailableCompletedNot AvailableDeep Vein Thrombosis / Pulmonary Embolism1
Not AvailableCompletedNot AvailableMajor Bleeding / Venous Thromboembolism1
Not AvailableCompletedNot AvailableNonvalvular Atrial Fibrillation1
Not AvailableCompletedNot AvailableStroke1
Not AvailableCompletedNot AvailableStroke, Ischemic1
Not AvailableCompletedNot AvailableUnsuspected Pulmonary Embolism1
Not AvailableCompletedNot AvailableVenous Thromboembolism1
Not AvailableEnrolling by InvitationNot AvailableDeep Venous Thrombosis / Pulmonary Embolism1
Not AvailableNot Yet RecruitingNot AvailableAnticoagulants Causing Adverse Effects in Therapeutic Use / Antiphospholipid Syndrome / Thrombotic events1
Not AvailableNot Yet RecruitingNot AvailableAtrial Fibrillation (AF)2
Not AvailableNot Yet RecruitingNot AvailableCerebral Vein Thrombosis / Ovarian vein thrombosis / Renal Vein Thrombosis / Retinal Vein Thrombosis / Splanchnic Vein Thrombosis1
Not AvailableNot Yet RecruitingNot AvailableStroke, Ischemic1
Not AvailableRecruitingNot AvailableAnticoagulants Causing Adverse Effects in Therapeutic Use / Atrial arrhythmias / Atrial Fibrillation (AF) / Congenital Heart Disease (CHD) / Thromboembolism1
Not AvailableRecruitingNot AvailableAnticoagulants and Bleeding Disorders / Venous Thromboembolism1
Not AvailableRecruitingNot AvailableAtrial Fibrillation (AF)1
Not AvailableRecruitingNot AvailableAtrial Fibrillation (AF) / Recurrent Venous Thromboembolism1
Not AvailableRecruitingNot AvailableCancer Patients / Central Venous Catheter Thrombosis / Upper Extremity Thrombosis1
Not AvailableRecruitingNot AvailableMyeloproliferative Neoplasms1
Not AvailableRecruitingNot AvailableObesity, Morbid1
Not AvailableRecruitingNot AvailableVenous Thromboembolism2
Not AvailableRecruitingPreventionAtrial Fibrillation (AF) / Stroke1
Not AvailableRecruitingScreeningCoagulation Disorders / Non Valvular Atrial Fibrillation1
Not AvailableRecruitingSupportive CareAtrial Fibrillation (AF) / Hemorrhage / Periodontal Diseases1
Not AvailableRecruitingTreatmentAcute DVT of Lower Extremity1
Not AvailableRecruitingTreatmentAtrial Fibrillation (AF) / Stroke, Acute1
Not AvailableRecruitingTreatmentBlood Clots / Deep Vein Thrombosis / Malignancies / Pulmonary Embolism / Venous Thromboembolism1
Not AvailableRecruitingTreatmentIschaemic Stroke / Stroke, Ischemic1
Not AvailableRecruitingTreatmentPersistent Atrial Fibrillation1
Not AvailableUnknown StatusNot AvailableStroke, Ischemic1
Not AvailableWithdrawnNot AvailableNon-valvular Atrial Fibrillation (NVAF)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral2.5 mg
TabletOral5 mg
Tablet, film coatedOral2.5 mg
Tablet, film coatedOral2.5 mg/1
Tablet, film coatedOral5 mg/1
Tablet, film coatedOral5 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2349330No2009-09-292019-12-17Canada
CA2461202No2011-07-122022-09-17Canada
US6413980No2002-07-022019-12-22Us
US6967208No2005-11-222023-02-03Us
US9326945No2016-05-032031-02-24Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)326.53[MSDS]
boiling point (°C)770.5[MSDS]
water solubility0.11mg/mLhttp://www.chemspider.com/Chemical-Structure.8358471.html?rid=2f601343-f676-4fcd-ad7d-1151c737876f
logP2.71[MSDS]
Predicted Properties
PropertyValueSource
Water Solubility0.0679 mg/mLALOGPS
logP2.22ALOGPS
logP1.83ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)13.12ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area110.76 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity126.9 m3·mol-1ChemAxon
Polarizability49.62 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9974
Blood Brain Barrier+0.9329
Caco-2 permeable-0.5308
P-glycoprotein substrateSubstrate0.6144
P-glycoprotein inhibitor IInhibitor0.6804
P-glycoprotein inhibitor IIInhibitor0.594
Renal organic cation transporterNon-inhibitor0.5628
CYP450 2C9 substrateNon-substrate0.8528
CYP450 2D6 substrateNon-substrate0.811
CYP450 3A4 substrateSubstrate0.764
CYP450 1A2 substrateNon-inhibitor0.9271
CYP450 2C9 inhibitorInhibitor0.5555
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.5
CYP450 3A4 inhibitorInhibitor0.5
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6447
Ames testNon AMES toxic0.5062
CarcinogenicityNon-carcinogens0.8796
BiodegradationNot ready biodegradable0.9965
Rat acute toxicity2.3038 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8351
hERG inhibition (predictor II)Inhibitor0.6205
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0210900000-941cd1e773f20ff3a0d7

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Phenylpiperidines
Direct Parent
Phenylpiperidines
Alternative Parents
Phenylpyrazoles / Pyridinecarboxamides / Methoxyanilines / 2-heteroaryl carboxamides / Pyrazole-5-carboxamides / Anisoles / Phenoxy compounds / Methoxybenzenes / Alkyl aryl ethers / Delta lactams
show 10 more
Substituents
Phenylpiperidine / Phenylpyrazole / Methoxyaniline / Pyridinecarboxamide / 2-heteroaryl carboxamide / Phenoxy compound / Anisole / Pyrazole-5-carboxamide / Phenol ether / Methoxybenzene
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
aromatic ether, lactam, piperidones, pyrazolopyridine (CHEBI:72296)

Targets

Details
1. Coagulation factor X
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serine-type endopeptidase activity
Specific Function
Factor Xa is a vitamin K-dependent glycoprotein that converts prothrombin to thrombin in the presence of factor Va, calcium and phospholipid during blood clotting.
Gene Name
F10
Uniprot ID
P00742
Uniprot Name
Coagulation factor X
Molecular Weight
54731.255 Da
References
  1. Spyropoulos AC: Investigational treatments of venous thromboembolism. Expert Opin Investig Drugs. 2007 Apr;16(4):431-40. [PubMed:17371192]
  2. Harenberg J, Wehling M: Current and future prospects for anticoagulant therapy: inhibitors of factor Xa and factor IIa. Semin Thromb Hemost. 2008 Feb;34(1):39-57. doi: 10.1055/s-2008-1066023. [PubMed:18393142]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Wang L, Zhang D, Raghavan N, Yao M, Ma L, Frost CE, Maxwell BD, Chen SY, He K, Goosen TC, Humphreys WG, Grossman SJ: In vitro assessment of metabolic drug-drug interaction potential of apixaban through cytochrome P450 phenotyping, inhibition, and induction studies. Drug Metab Dispos. 2010 Mar;38(3):448-58. doi: 10.1124/dmd.109.029694. Epub 2009 Nov 25. [PubMed:19940026]
  2. Apixaban FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Cada DJ, Levien TL, Baker DE: Apixaban. Hosp Pharm. 2013 Jun;48(6):494-509. doi: 10.1310/hpj4806-494. [PubMed:24421512]
  2. Apixaban FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Cada DJ, Levien TL, Baker DE: Apixaban. Hosp Pharm. 2013 Jun;48(6):494-509. doi: 10.1310/hpj4806-494. [PubMed:24421512]
  2. Budovich A, Zargarova O, Nogid A: Role of apixaban (eliquis) in the treatment and prevention of thromboembolic disease. P T. 2013 Apr;38(4):206-31. [PubMed:23785225]
  3. Wu Z, Lee D, Joo J, Shin JH, Kang W, Oh S, Lee do Y, Lee SJ, Yea SS, Lee HS, Lee T, Liu KH: CYP2J2 and CYP2C19 are the major enzymes responsible for metabolism of albendazole and fenbendazole in human liver microsomes and recombinant P450 assay systems. Antimicrob Agents Chemother. 2013 Nov;57(11):5448-56. doi: 10.1128/AAC.00843-13. Epub 2013 Aug 19. [PubMed:23959307]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible f...
Gene Name
CYP2J2
Uniprot ID
P51589
Uniprot Name
Cytochrome P450 2J2
Molecular Weight
57610.165 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Authors unspecified: Apixaban. After hip or knee replacement: LMWH remains the standard treatment. Prescrire Int. 2012 Sep;21(130):201-2, 204. [PubMed:23016247]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Budovich A, Zargarova O, Nogid A: Role of apixaban (eliquis) in the treatment and prevention of thromboembolic disease. P T. 2013 Apr;38(4):206-31. [PubMed:23785225]
  2. Apixaban FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Heyes N, Kapoor P, Kerr ID: Polymorphisms of the Multidrug Pump ABCG2: A Systematic Review of Their Effect on Protein Expression, Function, and Drug Pharmacokinetics. Drug Metab Dispos. 2018 Dec;46(12):1886-1899. doi: 10.1124/dmd.118.083030. Epub 2018 Sep 28. [PubMed:30266733]

Drug created on March 19, 2008 10:40 / Updated on February 20, 2020 17:09