Edoxaban

Edoxaban
Clinical data
Trade names	Savaysa, Lixiana, Roteas, others
Other names	DU-176b
AHFS/Drugs.com	Monograph
MedlinePlus	a614055
License data	US DailyMed: Edoxaban;
Routes of; administration	By mouth
ATC code	B01AF03 (WHO) ;
Legal status
Legal status	CA: ℞-only; US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	62%; Tmax 1–2 hours
Protein binding	55%
Metabolism	minimal CES1, CYP3A4/5, hydrolysis, glucuronidation
Elimination half-life	10–14 hours
Excretion	62% feces, 35% urine
Identifiers
	IUPAC name N'-(5-chloropyridin-2-yl)-N-[(1S,2R,4S)-4-(dimethylcarbamoyl)-2-[(5-methyl-6,7-dihydro-4H-[1,3]thiazolo[5,4-c]pyridine-2-carbonyl)amino]cyclohexyl]oxamide;
CAS Number	480449-70-5 ;
PubChem CID	10280735;
IUPHAR/BPS	7575;
DrugBank	DB09075 ;
ChemSpider	8456212 ;
UNII	NDU3J18APO;
KEGG	D09710 ;
ChEBI	CHEBI:85973 ;
CompTox Dashboard (EPA)	DTXSID50197398 ;
Chemical and physical data
Formula	C24H30ClN7O4S
Molar mass	548.06 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CCC2=C(C1)SC(=N2)C(=O)N[C@@H]3C[C@H](CC[C@@H]3NC(=O)C(=O)NC4=NC=C(C=C4)Cl)C(=O)N(C)C;
	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 ; Key:HGVDHZBSSITLCT-JLJPHGGASA-N ;
	(what is this?) (verify)

Edoxaban, sold under the brand name Lixiana among others, is an anticoagulant medication and a direct factor Xa inhibitor.^[3] It is taken by mouth.^[3]

Compared with warfarin, it has fewer drug interactions,^[6] and does not require regular assessment of blood samples for prothrombin time to assure safe anticoagulant therapy.^[7]

It was developed by Daiichi Sankyo and approved in July 2011, in Japan for prevention of venous thromboembolisms following lower-limb orthopedic surgery.^[8] It was also approved in the United States by the Food and Drug Administration (FDA) in January 2015, for the prevention of stroke and non–central-nervous-system systemic embolism.^[9]^[10] It was approved for use in the European Union in June 2015.^[4] It is on the World Health Organization's List of Essential Medicines.^[11]

^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
^ "Health Canada New Drug Authorizations: 2016 Highlights". Health Canada. 14 March 2017. Retrieved 7 April 2024.
^ ^a ^b ^c "Savaysa- edoxaban tosylate tablet, film coated". DailyMed. 24 April 2020. Retrieved 23 July 2020.
^ ^a ^b Cite error: The named reference Lixiana EPAR was invoked but never defined (see the help page).
^ "Roteas EPAR". European Medicines Agency (EMA). 4 May 2017. Retrieved 25 September 2020.
^ ^a ^b ^c ^d ^e Parasrampuria DA, Truitt KE (June 2016). "Pharmacokinetics and Pharmacodynamics of Edoxaban, a Non-Vitamin K Antagonist Oral Anticoagulant that Inhibits Clotting FactorXa". Clinical Pharmacokinetics. 55 (6): 641–55. doi:10.1007/s40262-015-0342-7. PMC 4875962. PMID 26620048.
^ Wang X, Ma Y, Hui X, et al. (April 2023). "Oral direct thrombin inhibitors or oral factor Xa inhibitors versus conventional anticoagulants for the treatment of deep vein thrombosis". The Cochrane Database of Systematic Reviews. 2023 (4): CD010956. doi:10.1002/14651858.CD010956.pub3. PMC 10105633. PMID 37058421.
^ "First market approval in Japan for Lixiana (Edoxaban)". Daiichi Sankyo Europe GmbH (Press release). 22 April 2011. Archived from the original on 6 November 2013.
^ O'Riordan M (9 January 2015). "FDA Approves Edoxaban for Stroke Prevention in AF and DVT/PE Prevention". Medscape. Retrieved 10 January 2015.
^ "Drug Approval Package: Savaysa (edoxaban tosylate) Tablets NDA #206316". U.S. Food and Drug Administration (FDA). 13 February 2015. Archived from the original on 12 September 2015. Retrieved 23 July 2020.
^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.

[1] "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.

[2] "Health Canada New Drug Authorizations: 2016 Highlights". Health Canada. 14 March 2017. Retrieved 7 April 2024.

[Savaysa_FDA_label-3] "Savaysa- edoxaban tosylate tablet, film coated". DailyMed. 24 April 2020. Retrieved 23 July 2020.

[Lixiana_EPAR-4] Cite error: The named reference Lixiana EPAR was invoked but never defined (see the help page).

[Roteas_EPAR-5] "Roteas EPAR". European Medicines Agency (EMA). 4 May 2017. Retrieved 25 September 2020.

[a-6] Parasrampuria DA, Truitt KE (June 2016). "Pharmacokinetics and Pharmacodynamics of Edoxaban, a Non-Vitamin K Antagonist Oral Anticoagulant that Inhibits Clotting FactorXa". Clinical Pharmacokinetics. 55 (6): 641–55. doi:10.1007/s40262-015-0342-7. PMC 4875962. PMID 26620048.

[wang-7] Wang X, Ma Y, Hui X, et al. (April 2023). "Oral direct thrombin inhibitors or oral factor Xa inhibitors versus conventional anticoagulants for the treatment of deep vein thrombosis". The Cochrane Database of Systematic Reviews. 2023 (4): CD010956. doi:10.1002/14651858.CD010956.pub3. PMC 10105633. PMID 37058421.

[url_Daiichi_Sankyo_Europe_GmbH-8] "First market approval in Japan for Lixiana (Edoxaban)". Daiichi Sankyo Europe GmbH (Press release). 22 April 2011. Archived from the original on 6 November 2013.

[9] O'Riordan M (9 January 2015). "FDA Approves Edoxaban for Stroke Prevention in AF and DVT/PE Prevention". Medscape. Retrieved 10 January 2015.

[10] "Drug Approval Package: Savaysa (edoxaban tosylate) Tablets NDA #206316". U.S. Food and Drug Administration (FDA). 13 February 2015. Archived from the original on 12 September 2015. Retrieved 23 July 2020.

[WHO22nd-11] World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.

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