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Identification
- Summary
Edoxaban is a novel oral anticoagulant used for reducing the risk of stroke and systemic embolism (SE) in patients with nonvalvular atrial fibrillation (NVAF).
- Brand Names
- Lixiana, Savaysa
- Generic Name
- Edoxaban
- DrugBank Accession Number
- DB09075
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Edoxaban (DB09075)
- Weight
- Average: 548.06
Monoisotopic: 547.1768513 - Chemical Formula
- C24H30ClN7O4S
- Synonyms
- Edoxaban
- External IDs
- DU 176
- DU 176b
- DU-176
- DU-176b
Pharmacology
- Indication
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.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Deep vein thrombosis •••••••••••• Treatment of Pulmonary embolism •••••••••••• Prophylaxis of Stroke •••••••••••• Prophylaxis of Systemic embolism •••••••••••• - Contraindications & Blackbox Warnings
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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.
Target Actions Organism ACoagulation factor X inhibitorHumans - Absorption
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%.
- Metabolism
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.
- Clearance
22 L/hr
- Adverse Effects
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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.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Edoxaban which could result in a higher serum level. Abciximab The risk or severity of bleeding can be increased when Edoxaban is combined with Abciximab. Abemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Edoxaban. Abrocitinib The serum concentration of Edoxaban can be increased when it is combined with Abrocitinib. Aceclofenac The risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with Edoxaban. - Food Interactions
- Avoid herbs and supplements with anticoagulant/antiplatelet activity. Additive anticoagulant activity may increase the risk of bleeding. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.
- Take with or without food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Edoxaban tosylate 32W99UE810 480449-71-6 ZLFZITWZOYXXAW-QXXZOGQOSA-N Edoxaban tosylate monohydrate 972203R4EW 1229194-11-9 PSMMNJNZVZZNOI-SJILXJHISA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Lixiana Tablet, film coated 30 mg Oral Daiichi Sankyo Europe, Gmb H 2016-09-08 Not applicable EU 
Lixiana Tablet, film coated 60 mg Oral Daiichi Sankyo Europe, Gmb H 2016-09-08 Not applicable EU Lixiana Tablet, film coated 30 mg Oral Daiichi Sankyo Europe, Gmb H 2016-09-08 Not applicable EU Lixiana Tablet, film coated 60 mg Oral Daiichi Sankyo Europe, Gmb H 2016-09-08 Not applicable EU Lixiana Tablet, film coated 30 mg Oral Daiichi Sankyo Europe, Gmb H 2016-09-08 Not applicable EU
Categories
- ATC Codes
- B01AF03 — Edoxaban
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- 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.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- 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 show 8 more
- Substituents
- 2-heteroaryl carboxamide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole show 24 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- tertiary amino compound, monocarboxylic acid amide, chloropyridine, thiazolopyridine (CHEBI:85973)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- NDU3J18APO
- CAS number
- 480449-70-5
- InChI Key
- HGVDHZBSSITLCT-JLJPHGGASA-N
- InChI
- InChI=1S/C24H30ClN7O4S/c1-31(2)24(36)13-4-6-15(27-20(33)21(34)30-19-7-5-14(25)11-26-19)17(10-13)28-22(35)23-29-16-8-9-32(3)12-18(16)37-23/h5,7,11,13,15,17H,4,6,8-10,12H2,1-3H3,(H,27,33)(H,28,35)(H,26,30,34)/t13-,15-,17+/m0/s1
- IUPAC Name
- N'-(5-chloropyridin-2-yl)-N-[(1S,2R,4S)-4-(dimethylcarbamoyl)-2-{5-methyl-4H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridine-2-amido}cyclohexyl]ethanediamide
- SMILES
- CN(C)C(=O)[C@H]1CC[C@H](NC(=O)C(=O)NC2=NC=C(Cl)C=C2)[C@@H](C1)NC(=O)C1=NC2=C(CN(C)CC2)S1
References
- General References
- Turpie AG: New oral anticoagulants in atrial fibrillation. Eur Heart J. 2008 Jan;29(2):155-65. Epub 2007 Dec 19. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- FDA Approved Drug Products: Savaysa (edoxaban tosylate) tablets for oral use [Link]
- External Links
- KEGG Drug
- D09546
- PubChem Compound
- 10280735
- PubChem Substance
- 310265005
- ChemSpider
- 8456212
- BindingDB
- 50328731
- 1599538
- ChEBI
- 85973
- ChEMBL
- CHEMBL1269025
- ZINC
- ZINC000043200832
- PharmGKB
- PA166128806
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Edoxaban
- FDA label
- Download (600 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Not Available Atrial Fibrillation 2 somestatus stop reason just information to hide Not Available Active Not Recruiting Not Available Atrial Fibrillation or Flutter / Valvular Heart Diseases 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Not Available Neoplasm / Systemic Embolism 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Not Available Non-valvular Atrial Fibrillation 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Treatment Atrial Fibrillation / Stroke, Acute 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 15 mg Tablet Oral 20.210 mg Tablet Oral 30 mg Tablet Oral 60 mg Tablet, coated Oral 15 mg Tablet, film coated Oral Tablet, coated Oral 30 mg Tablet, coated Oral 60 mg Tablet, film coated Oral 15 mg Tablet, film coated Oral 30 mg Tablet, film coated Oral 60 mg Tablet, film coated Oral 15 mg/1 Tablet, film coated Oral 30 mg/1 Tablet, film coated Oral 60 mg/1 - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US2013026553 No 2011-08-22 2031-08-22 US 
US9149532 No 2015-10-06 2028-03-28 US US7365205 No 2008-04-29 2023-06-12 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source pKa 6.7 FDA Label - Predicted Properties
Property Value Source Water Solubility 0.0114 mg/mL ALOGPS logP 1.61 ALOGPS logP 0.9 Chemaxon logS -4.7 ALOGPS pKa (Strongest Acidic) 10.74 Chemaxon pKa (Strongest Basic) 6.33 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 136.63 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 140.14 m3·mol-1 Chemaxon Polarizability 56.31 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 217.6334 predictedDeepCCS 1.0 (2019) [M+H]+ 219.52882 predictedDeepCCS 1.0 (2019) [M+Na]+ 225.3137 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General 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. Factor Xa activates pro-inflammatory signaling pathways in a protease-activated receptor (PAR)-dependent manner (PubMed:24041930, PubMed:30568593, PubMed:34831181). Up-regulates expression of protease-activated receptors (PARs) F2R, F2RL1 and F2RL2 in dermal microvascular endothelial cells (PubMed:35738824). Triggers the production of pro-inflammatory cytokines, such as MCP-1/CCL2 and IL6, in cardiac fibroblasts and umbilical vein endothelial cells in PAR-1 (F2R)-dependent manner (PubMed:30568593, PubMed:34831181). Triggers the production of pro-inflammatory cytokines, such as MCP-1/CCL2, IL6, TNF-alpha/TNF, IL-1beta/IL1B, IL8/CXCL8 and IL18, in endothelial cells and atrial tissues (PubMed:24041930, PubMed:35738824, PubMed:9780208). Induces expression of adhesion molecules, such as ICAM1, VCAM1 and SELE, in endothelial cells and atrial tissues (PubMed:24041930, PubMed:35738824, PubMed:9780208). Increases expression of phosphorylated ERK1/2 in dermal microvascular endothelial cells and atrial tissues (PubMed:24041930, PubMed:35738824). Triggers activation of the transcription factor NF-kappa-B in dermal microvascular endothelial cells and atrial tissues (PubMed:24041930, PubMed:35738824). Up-regulates expression of plasminogen activator inhibitor 1 (SERPINE1) in atrial tissues (PubMed:24041930)
- Specific Function
- calcium ion binding
- Gene Name
- F10
- Uniprot ID
- P00742
- Uniprot Name
- Coagulation factor X
- Molecular Weight
- 54731.255 Da
References
- Turpie AG: New oral anticoagulants in atrial fibrillation. Eur Heart J. 2008 Jan;29(2):155-65. Epub 2007 Dec 19. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- 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. [Article]
Drug created at May 15, 2015 16:35 / Updated at October 07, 2024 13:24