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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H30ClN7O4S
Molecular Weight 548.058
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EDOXABAN

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)C3=NC4=C(CN(C)CC4)S3

InChI

InChIKey=HGVDHZBSSITLCT-JLJPHGGASA-N
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

HIDE SMILES / InChI

Description

Edoxaban (DU-176b, trade names Savaysa, Lixiana) is a selective factor Xa inhibitor reduces thrombin generation and thrombus formation and is an orally bioavailable anticoagulant drug. It was developed by Daiichi Sankyo to reduce the risk of stroke and systemic embolism in patients with nonvalvular atrial fibrillation (NVAF) and for the treatment of deep vein thrombosis and pulmonary embolism following 5-10 days of initial therapy with a parenteral anticoagulant.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.561 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
SAVAYSA
Primary
SAVAYSA
Primary
SAVAYSA
PubMed

PubMed

TitleDatePubMed
New oral anticoagulants in atrial fibrillation.
2008 Jan
Clinical safety, tolerability, pharmacokinetics, and pharmacodynamics of the novel factor Xa inhibitor edoxaban in healthy volunteers.
2010 Jul
Factor Xa inhibitors: next-generation antithrombotic agents.
2010 Sep 9
Comparative efficacy and safety of the non-vitamin K antagonist oral anticoagulants for patients with nonvalvular atrial fibrillation.
2015 Mar
Overview of the new oral anticoagulants: opportunities and challenges.
2015 May
Pharmacokinetics and Pharmacodynamics of Edoxaban, a Non-Vitamin K Antagonist Oral Anticoagulant that Inhibits Clotting Factor Xa.
2016 Jun
Patents

Sample Use Guides

In Vivo Use Guide
Nonvalvular Atrial Fibrillation: 60 mg taken orally once daily Deep Vein Thrombosis and Pulmonary Embolism: 60 mg taken orally once daily following 5 to 10 days of initial therapy with a parenteral anticoagulant. If a dose of is missed, the dose should be taken as soon as possible on the same day. Dosing should resume the next day according to the normal dosing schedule. The dose should not be doubled to make up for a missed dose.
Route of Administration: Oral
In Vitro Use Guide
In vitro, FXa inhibition, specificity and anticoagulant activities were examined. DU-176b (Edoxaban) inhibited FXa with Ki values of 0.561 nm for free FXa, 2.98 nm for prothrombinase, and exhibited >10 000-fold selectivity for FXa. In human plasma, DU-176b doubled prothrombin time and activated partial thromboplastin time at concentrations of 0.256 and 0.508 microm, respectively.
Name Type Language
EDOXABAN
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
N-(5-CHLOROPYRIDIN-2-YL)-N'-((1S,2R,4S)-4-(N,N-DIMETHYLCARBAMOYL)-2-(5-METHYL-4,5,6,7- TETRAHYDRO(1,3)THIAZOLO(5,4-C)PYRIDINE-2-CARBOXAMIDO)CYCLOHEXYL)OXAMIDE
Systematic Name English
EDOXABAN [MART.]
Common Name English
EDOXABAN [MI]
Common Name English
EDOXABAN [USAN]
Common Name English
DU-176
Code English
ETHANEDIAMIDE, N1-(5-CHLORO-2-PYRIDINYL)-N2-((1S,2R,4S)-4- ((DIMETHYLAMINO)CARBONYL)- 2-(((4,5,6,7-TETRAHYDRO-5-METHYLTHIAZOLO(5,4-C)PYRIDIN-2-YL)CARBONYL)AMINO)CYCLOHEXYL)-
Common Name English
EDOXABAN [INN]
Common Name English
EDOXABAN [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC B01AF03
Created by admin on Tue Mar 06 10:57:24 UTC 2018 , Edited by admin on Tue Mar 06 10:57:24 UTC 2018
Code System Code Type Description
JAPANESE REVIEW
LIXIANA
Created by admin on Tue Mar 06 10:57:24 UTC 2018 , Edited by admin on Tue Mar 06 10:57:24 UTC 2018
PRIMARY APPROVED APRIL 2011
JAPANESE REVIEW
LIXIANA
Created by admin on Tue Mar 06 10:57:24 UTC 2018 , Edited by admin on Tue Mar 06 10:57:24 UTC 2018
PRIMARY APPROVED APRIL 2011
MERCK INDEX
M4832
Created by admin on Tue Mar 06 10:57:24 UTC 2018 , Edited by admin on Tue Mar 06 10:57:24 UTC 2018
PRIMARY Merck Index
INN
8982
Created by admin on Tue Mar 06 10:57:24 UTC 2018 , Edited by admin on Tue Mar 06 10:57:24 UTC 2018
PRIMARY
RXCUI
1599538
Created by admin on Tue Mar 06 10:57:24 UTC 2018 , Edited by admin on Tue Mar 06 10:57:24 UTC 2018
PRIMARY RxNorm
MESH
C552171
Created by admin on Tue Mar 06 10:57:24 UTC 2018 , Edited by admin on Tue Mar 06 10:57:24 UTC 2018
PRIMARY
WIKIPEDIA
Edoxaban
Created by admin on Tue Mar 06 10:57:24 UTC 2018 , Edited by admin on Tue Mar 06 10:57:24 UTC 2018
PRIMARY
ChEMBL
CHEMBL1269025
Created by admin on Tue Mar 06 10:57:24 UTC 2018 , Edited by admin on Tue Mar 06 10:57:24 UTC 2018
PRIMARY
EVMPD
SUB32701
Created by admin on Tue Mar 06 10:57:24 UTC 2018 , Edited by admin on Tue Mar 06 10:57:24 UTC 2018
PRIMARY
DRUG BANK
DB09075
Created by admin on Tue Mar 06 10:57:24 UTC 2018 , Edited by admin on Tue Mar 06 10:57:24 UTC 2018
PRIMARY
IUPHAR
7575
Created by admin on Tue Mar 06 10:57:24 UTC 2018 , Edited by admin on Tue Mar 06 10:57:24 UTC 2018
PRIMARY
CAS
480449-70-5
Created by admin on Tue Mar 06 10:57:24 UTC 2018 , Edited by admin on Tue Mar 06 10:57:24 UTC 2018
PRIMARY
NCI_THESAURUS
C96539
Created by admin on Tue Mar 06 10:57:24 UTC 2018 , Edited by admin on Tue Mar 06 10:57:24 UTC 2018
PRIMARY
EPA CompTox
480449-70-5
Created by admin on Tue Mar 06 10:57:24 UTC 2018 , Edited by admin on Tue Mar 06 10:57:24 UTC 2018
PRIMARY
LactMed
480449-70-5
Created by admin on Tue Mar 06 10:57:24 UTC 2018 , Edited by admin on Tue Mar 06 10:57:24 UTC 2018
PRIMARY
PUBCHEM
10280735
Created by admin on Tue Mar 06 10:57:24 UTC 2018 , Edited by admin on Tue Mar 06 10:57:24 UTC 2018
PRIMARY SWITZERF