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Accession Number
Small Molecule

Edoxaban is a member of the Novel Oral Anti-Coagulants (NOACs) class of drugs, and is a rapidly acting, oral, selective factor Xa inhibitor. By inhibiting factor Xa, a key protein in the coagulation cascade, edoxaban prevents the stepwise amplification of protein factors needed to form blood clots. It is indicated to reduce the risk of stroke and systemic embolism (SE) in patients with nonvalvular atrial fibrillation (NVAF) and for the treatment of deep vein thrombosis (DVT) and pulmonary embolism (PE) following 5-10 days of initial therapy with a parenteral anticoagulant. Traditionally, warfarin, a vitamin K antagonist, was used for stroke prevention in these individuals but effective use of this drug is limited by it's delayed onset, narrow therapeutic window, need for regular monitoring and INR testing, and numerous drug-drug and drug-food interactions. This has prompted enthusiasm for newer agents such as dabigatran, apixaban, and rivaroxaban for effective clot prevention. In addition to once daily dosing, the benefits over warfarin also include significant reductions in hemorrhagic stroke and GI bleeding, and improved compliance, which is beneficial as many patients will be on lifelong therapy.

  • Edoxaban
External IDs
DU 176 / DU 176b / DU-176 / DU-176b
Product Ingredients
IngredientUNIICASInChI Key
Edoxaban tosylate32W99UE810480449-71-6ZLFZITWZOYXXAW-QXXZOGQOSA-N
Edoxaban tosylate monohydrate972203R4EW1229194-11-9PSMMNJNZVZZNOI-SJILXJHISA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LixianaTablet, film coated30 mgOralDaiichi Sankyo Europe, Gmb H2015-06-19Not applicableEu
LixianaTablet, film coated60 mgOralDaiichi Sankyo Europe, Gmb H2015-06-19Not applicableEu
LixianaTablet, film coated60 mgOralDaiichi Sankyo Europe, Gmb H2015-06-19Not applicableEu
LixianaTablet, film coated15 mgOralDaiichi Sankyo Europe, Gmb H2015-06-19Not applicableEu
LixianaTablet, film coated30 mgOralDaiichi Sankyo Europe, Gmb H2015-06-19Not applicableEu
LixianaTablet, film coated30 mgOralDaiichi Sankyo Europe, Gmb H2015-06-19Not applicableEu
LixianaTablet, film coated15 mgOralDaiichi Sankyo Europe, Gmb H2015-06-19Not applicableEu
LixianaTablet, film coated60 mgOralDaiichi Sankyo Europe, Gmb H2015-06-19Not applicableEu
LixianaTablet, film coated60 mgOralDaiichi Sankyo Europe, Gmb H2015-06-19Not applicableEu
LixianaTablet, film coated30 mgOralDaiichi Sankyo Europe, Gmb H2015-06-19Not applicableEu
Additional Data Available
  • Application Number
    Application Number

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  • Product Code
    Product Code

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CAS number
Average: 548.06
Monoisotopic: 547.1768513
Chemical Formula
InChI Key



Edoxaban is indicated for reducing the risk of stroke and systemic embolism (SE) in patients with nonvalvular atrial fibrillation (NVAF). However, it should not be used in patients with creatinine clearance (CrCL) > 95 mL/min because of increased risk of ischemic stroke compared to warfarin at the highest dose studied (60 mg). It is also indicated for the treatment of deep vein thrombosis (DVT) and pulmonary embolism (PE) following 5-10 days of initial therapy with a parenteral anticoagulant.

Associated Conditions

Administration of edoxaban results in prolongation of clotting time tests such as aPTT (activated partial thromboplastin time), PT (prothrombin time), and INR (international normalized ratio).

Mechanism of action

Edoxaban is a selective inhibitor of factor Xa, a serine endopeptidase of the clotting cascade required for cleavage of prothrombin into thrombin.

ACoagulation factor X
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

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

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Following oral administration, peak plasma edoxaban concentrations are observed within 1-2 hours. Absolute bioavailability is 62%.

Volume of distribution

The steady state volume of distribution is 107 L.

Protein binding

In vitro plasma protein binding is ~55%.


Edoxaban is not extensively metabolized by CYP3A4 resulting in minimal drug-drug interactions. However, it does interact with drugs that inhibit p-gp (p-glycoprotein), which is used to transport edoxaban across the intestinal wall. Unchanged edoxaban is the predominant form in plasma. There is minimal metabolism via hydrolysis (mediated by carboxylesterase 1), conjugation, and oxidation by CYP3A4. The predominant metabolite M-4, formed by hydrolysis, is human-specific and active and reaches less than 10% of the exposure of the parent compound in healthy subjects. Exposure to the other metabolites is less than 5% of exposure to edoxaban.

Route of elimination

Edoxaban is eliminated primarily as unchanged drug in urine. Renal clearance (11 L/hour) accounts for approximately 50% of the total clearance of edoxaban (22 L/hour). Metabolism and biliary/intestinal excretion account for the remaining clearance.

Half life

The terminal elimination half-life of edoxaban following oral administration is 10 to 14 hours.


22 L/hr


Premature discontinuation of any oral anticoagulant, including edoxaban, in the absence of adequate alternative anticoagulation increases the risk of ischemic events. If edoxaban is discontinued for reasons other than pathological bleeding or completion of a course of therapy, consider the use of another anticoagulant. Edoxaban increases the risk of potentially fatal major bleeding such as intracranial hemorrhage and gastrointestinal bleeding. Patients should be educated on how to watch for signs of major and minor bleeding and when to seek medical help. Co-administration of other anti-coagulants, anti-platelets, or thrombolytics may increase the risk of bleeding and should therefore be avoided.

Affected organisms
Not Available
Not Available
Pharmacogenomic Effects/ADRs
Not Available


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.
(1,2,6,7-3H)Testosterone(1,2,6,7-3H)Testosterone may increase the anticoagulant activities of Edoxaban.
(R)-warfarinThe risk or severity of bleeding can be increased when Edoxaban is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Edoxaban is combined with (S)-Warfarin.
1-Testosterone1-Testosterone may increase the anticoagulant activities of Edoxaban.
18-methyl-19-nortestosterone18-methyl-19-nortestosterone may increase the anticoagulant activities of Edoxaban.
3,5-Diiodotyrosine3,5-Diiodotyrosine may increase the anticoagulant activities of Edoxaban.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Edoxaban is combined with 4-hydroxycoumarin.
4-Hydroxytestosterone4-Hydroxytestosterone may increase the anticoagulant activities of Edoxaban.
5beta-dihydrotestosterone5beta-dihydrotestosterone may increase the anticoagulant activities of Edoxaban.
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 Edoxaban.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity

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  • Evidence Level
    Evidence Level

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  • Action

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Food Interactions
Not Available


General References
  1. Turpie AG: New oral anticoagulants in atrial fibrillation. Eur Heart J. 2008 Jan;29(2):155-65. Epub 2007 Dec 19. [PubMed:18096568]
  2. Ogata K, Mendell-Harary J, Tachibana M, Masumoto H, Oguma T, Kojima M, Kunitada S: Clinical safety, tolerability, pharmacokinetics, and pharmacodynamics of the novel factor Xa inhibitor edoxaban in healthy volunteers. J Clin Pharmacol. 2010 Jul;50(7):743-53. doi: 10.1177/0091270009351883. Epub 2010 Jan 15. [PubMed:20081065]
  3. Yeh CH, Hogg K, Weitz JI: Overview of the new oral anticoagulants: opportunities and challenges. Arterioscler Thromb Vasc Biol. 2015 May;35(5):1056-65. doi: 10.1161/ATVBAHA.115.303397. Epub 2015 Mar 19. [PubMed:25792448]
  4. Senoo K, Lip GY: Comparative efficacy and safety of the non-vitamin K antagonist oral anticoagulants for patients with nonvalvular atrial fibrillation. Semin Thromb Hemost. 2015 Mar;41(2):146-53. doi: 10.1055/s-0035-1544156. Epub 2015 Feb 15. [PubMed:25682085]
  5. Parasrampuria DA, Truitt KE: Pharmacokinetics and Pharmacodynamics of Edoxaban, a Non-Vitamin K Antagonist Oral Anticoagulant that Inhibits Clotting Factor Xa. Clin Pharmacokinet. 2015 Nov 30. [PubMed:26620048]
External Links
PubChem Compound
PubChem Substance
RxList Drug Page Drug Page
ATC Codes
B01AF03 — Edoxaban
AHFS Codes
  • 20:12.04.14 — Direct Factor Xa Inhibitors
FDA label
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Clinical Trials

Clinical Trials
1CompletedSupportive CareBleeding1
1RecruitingBasic ScienceDeep Vein Thrombosis / Venous Thromboembolism (VTE) / Venous Thrombosis Pediatrics1
2CompletedOtherAnticoagulation Reversal / Healthy Volunteers1
2CompletedPreventionArthroplasty, Replacement, Hip / Deep Vein Thrombosis / Embolism and Thrombosis / Thromboembolism / Thrombotic events / Venous Thromboembolism (VTE)1
2CompletedPreventionArthroplasty, Replacement, Hip / Thrombotic events1
2CompletedPreventionAtrial Fibrillation (AF)1
2CompletedPreventionAtrial Fibrillation (AF) / Stroke1
2CompletedPreventionAtrial Fibrillation (AF) / Thromboembolism1
2CompletedPreventionDeep Vein Thrombosis / Total Knee Arthroplasty (TKA) / Venous Thromboembolism (VTE)1
2CompletedPreventionHip Replacement Surgery / Thrombotic events1
2CompletedTreatmentCoagulation / Human Immunodeficiency Virus (HIV) Infections / Inflammatory Reaction1
2CompletedTreatmentDeep Vein Thrombosis / Thrombosis, Venous1
2CompletedTreatmentHealthy Volunteers1
2CompletedTreatmentPeripheral Arterial Disease (PAD)1
2Not Yet RecruitingTreatmentAnticoagulant-induced Bleeding1
2RecruitingPreventionAcute Ischemic Stroke (AIS)1
2RecruitingTreatmentAtrial Fibrillation (AF)1
2, 3RecruitingTreatmentCorrection of Cancer-related Coagulopathy With Novel Oral Anticoagulant (Edoxaban)1
2, 3Unknown StatusTreatmentCerebral Infarctions / Ischaemia / Stroke1
3Active Not RecruitingPreventionAtrial Fibrillation (AF)1
3CompletedPreventionAtrial Fibrillation (AF) / Stroke / Systemic Embolism1
3CompletedPreventionNon-valvular Atrial Fibrillation (NVAF)1
3CompletedPreventionPrevention / Venous Thromboembolism (VTE)1
3CompletedPreventionVenous Thromboembolism (VTE)3
3CompletedTreatmentAtrial Fibrillation (AF)3
3CompletedTreatmentDeep Vein Thrombosis / Malignancies / Pulmonary Embolism / Venous Thromboembolism (VTE)1
3CompletedTreatmentDeep Vein Thrombosis / Pulmonary Embolism / Thromboembolism / Thrombosis, Venous / Venous Thromboembolism (VTE)1
3CompletedTreatmentMV(Mitral Valve) Repair1
3Not Yet RecruitingPreventionStroke, Ischemic1
3RecruitingPreventionAnticoagulant Drugs / Cardiac Diseases1
3RecruitingPreventionAtrial Fibrillation (AF) / Atrial Flutter / Intracranial Hemorrhage, Hypertensive / Intracranial Hemorrhages / Intraventricular Hemorrhage / Microhaemorrhage / Small Vessel Cerebrovascular Disease / Subarachnoid Hemorrhage / Subdural haematoma1
3RecruitingPreventionAtrial Fibrillation (AF) / Intracerebral Hemorrhage1
3RecruitingPreventionAtrial Fibrillation (AF) / Intracranial Hemorrhages1
3RecruitingPreventionAtrial Fibrillation (AF) / Stroke1
3RecruitingPreventionAtrial High Rate Episodes1
3RecruitingTreatmentAtrial Fibrillation (AF)1
3RecruitingTreatmentDeep Vein Thrombosis / Pulmonary Embolism / Venous Thromboembolism (VTE)1
4CompletedBasic ScienceDisorders, Blood Coagulation1
4CompletedTreatmentCoronary Artery Disease1
4Not Yet RecruitingTreatmentAtrial Fibrillation (AF) / Ischaemic Heart Diseases1
4Not Yet RecruitingTreatmentAtrial Fibrillation (AF) / Left Atrial Appendage Thrombosis1
4Not Yet RecruitingTreatmentLeft Atrial Appendage Closure / Non-valvular Atrial Fibrillation (NVAF)1
4RecruitingPreventionAtrial Fibrillation (AF)3
4RecruitingPreventionBleeding / Left Atrial Appendage Closure / Stroke / Thrombotic events / Transient Ischaemic Attack (TIA)1
4RecruitingTreatmentAnticoagulant / Neoplasms / Thrombosis, Venous1
4RecruitingTreatmentAtrial Fibrillation (AF) / Chronic Stable Angina Pectoris / Coronary Artery Disease / Stable Angina (SA)1
4RecruitingTreatmentDeep Vein Thrombosis / Pulmonary Embolism1
4RecruitingTreatmentDiabetes Mellitus (DM)1
4RecruitingTreatmentMalignancies / Thromboembolism1
4TerminatedTreatmentAtrial Fibrillation (AF)1
Not AvailableActive Not RecruitingNot AvailableAtrial Fibrillation (AF)3
Not AvailableActive Not RecruitingNot AvailableVenous Thromboembolism (VTE)2
Not AvailableActive Not RecruitingHealth Services ResearchNeoplasms / Thrombosis, Venous1
Not AvailableCompletedNot AvailableAtrial Fibrillation (AF)2
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedBasic ScienceAtrial Fibrillation (AF)1
Not AvailableEnrolling by InvitationNot AvailableDeep Venous Thrombosis / Pulmonary Embolism1
Not AvailableNot Yet RecruitingNot AvailableAtrial Fibrillation (AF)1
Not AvailableNot Yet RecruitingNot AvailableCerebral Vein Thrombosis / Ovarian vein thrombosis / Renal Vein Thrombosis / Retinal Vein Thrombosis / Splanchnic Vein Thrombosis1
Not AvailableNot Yet RecruitingTreatmentAtrial Fibrillation (AF) / Stroke, Acute1
Not AvailableRecruitingNot AvailableAcute Ischemic Stroke (AIS) / Anticoagulant / Antiplatelet / Atrial Fibrillation (AF) / Coronary Artery Atherosclerosis / Extracranial Atherosclerosis / Intracranial Atherosclerosis / Peripheral artery stenosis1
Not AvailableRecruitingNot AvailableAnticoagulants and Bleeding Disorders / Venous Thromboembolism (VTE)1
Not AvailableRecruitingNot AvailableAtrial Fibrillation (AF)2
Not AvailableRecruitingNot AvailableAtrial Fibrillation (AF) / Atrial Fibrillation or Flutter1
Not AvailableRecruitingNot AvailableAtrial Fibrillation (AF) / Recurrent Venous Thromboembolism1
Not AvailableRecruitingNot AvailableHeart Failure1
Not AvailableRecruitingPreventionAnticoagulants and Bleeding Disorders / Atrial Fibrillation (AF)1
Not AvailableRecruitingPreventionAtrial Fibrillation (AF) / Stroke1
Not AvailableRecruitingTreatmentAcute DVT of Lower Extremity1
Not AvailableRecruitingTreatmentBlood Clots / Deep Vein Thrombosis / Malignancies / Pulmonary Embolism / Venous Thromboembolism (VTE)1
Not AvailableRecruitingTreatmentIschaemic Stroke / Stroke, Ischemic1


Not Available
Not Available
Dosage forms
Tablet, film coatedOral15 mg
Tablet, film coatedOral30 mg
Tablet, film coatedOral60 mg
Tablet, film coatedOral15 mg/1
Tablet, film coatedOral30 mg/1
Tablet, film coatedOral60 mg/1
Not Available
Patent NumberPediatric ExtensionApprovedExpires (estimated)
Additional Data Available
  • Filed On
    Filed On

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

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Experimental Properties
pKa6.7FDA Label
Predicted Properties
Water Solubility0.0114 mg/mLALOGPS
pKa (Strongest Acidic)10.74ChemAxon
pKa (Strongest Basic)6.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area136.63 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity140.14 m3·mol-1ChemAxon
Polarizability56.31 Å3ChemAxon
Number of Rings4ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available


Mass Spec (NIST)
Not Available
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


This compound belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
Organic compounds
Super Class
Organic acids and derivatives
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Gamma amino acids and derivatives
Alternative Parents
Alpha amino acid amides / 2-heteroaryl carboxamides / Thiazolecarboxamides / N-arylamides / Aralkylamines / Aryl chlorides / Imidolactams / Pyridines and derivatives / Tertiary carboxylic acid amides / Heteroaromatic compounds
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Alpha-amino acid amide / Gamma amino acid or derivatives / Alpha-amino acid or derivatives / 2-heteroaryl carboxamide / Thiazolecarboxamide / Thiazolecarboxylic acid or derivatives / N-arylamide / Aralkylamine / Aryl chloride / Aryl halide
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Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, monocarboxylic acid amide, chloropyridine, thiazolopyridine (CHEBI:85973)


Pharmacological action
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
Uniprot ID
Uniprot Name
Coagulation factor X
Molecular Weight
54731.255 Da
  1. Turpie AG: New oral anticoagulants in atrial fibrillation. Eur Heart J. 2008 Jan;29(2):155-65. Epub 2007 Dec 19. [PubMed:18096568]


Pharmacological action
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
Uniprot ID
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
  1. Mikkaichi T, Yoshigae Y, Masumoto H, Imaoka T, Rozehnal V, Fischer T, Okudaira N, Izumi T: Edoxaban transport via P-glycoprotein is a key factor for the drug's disposition. Drug Metab Dispos. 2014 Apr;42(4):520-8. doi: 10.1124/dmd.113.054866. Epub 2014 Jan 23. [PubMed:24459178]

Drug created on May 15, 2015 10:35 / Updated on November 14, 2019 20:06