Edoxaban

Edoxaban

Clinical data
Trade names	Savaysa, Lixiana
AHFS/Drugs.com	Monograph
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Oral
ATC code	B01AF03 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	62%; Tmax 1–2 hours
Protein binding	55%
Metabolism	Minimal hepatic
Biological half-life	10–14 hours
Excretion	50% renal; <50% bile
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 N
PubChem CID	10280735
IUPHAR/BPS	7575
DrugBank	DB09075 Y
ChemSpider	8456212 N
UNII	NDU3J18APO
KEGG	D09710 N
ChEBI	CHEBI:85973 N
Chemical and physical data
Formula	C24H30ClN7O4S
Molar mass	548.056 g/mol
3D model (Jmol)	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 N Key:HGVDHZBSSITLCT-JLJPHGGASA-N N
NY (what is this?)

Edoxaban (DU-176b, trade names Savaysa, Lixiana) is an oral anticoagulant drug which acts as a direct factor Xa inhibitor. It was developed by Daiichi Sankyo and approved in July 2011 in Japan for prevention of venous thromboembolisms (VTE) following lower-limb orthopedic surgery. It was also approved by the FDA in January 2015 for the prevention of stroke and non–central-nervous-system systemic embolism.

US FDA-labeled indications:

Edoxaban is contraindicated in nonvalvular atrial fibrillation (NVAF) patients with a creatinine clearance (CrCl) greater than 95 mL/minute because of an increased risk of ischemic stroke compared to warfarin.

It is also contraindicated in patients with active pathological bleeding.

Spinal or epidural hematomas resulting in long-term or permanent paralysis may occur with neuraxial anesthesia (epidural or spinal anesthesia) or spinal/epidural puncture; the risk is increased by the use of indwelling epidural catheters, concomitant administration of other drugs that affect hemostasis (eg, NSAIDs, platelet inhibitors, other anticoagulants), in patients with a history of traumatic or repeated epidural or spinal punctures, a history of spinal deformity or surgery, or if optimal timing between the administration of edoxaban and neuraxial procedures is not known.

More common

Less common

Rare

Edoxaban inhibits free factor Xa and prothrombinase activity and inhibits thrombin-induced platelet aggregation. Inhibition of factor Xa in the coagulation cascade reduces thrombin generation and thrombus formation.