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Details

Stereochemistry ACHIRAL
Molecular Formula C27H30N4O4
Molecular Weight 474.5515
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DAREXABAN

SMILES

COC1=CC=C(C=C1)C(=O)NC2=CC=CC(O)=C2NC(=O)C3=CC=C(C=C3)N4CCCN(C)CC4

InChI

InChIKey=IJNIQYINMSGIPS-UHFFFAOYSA-N
InChI=1S/C27H30N4O4/c1-30-15-4-16-31(18-17-30)21-11-7-19(8-12-21)27(34)29-25-23(5-3-6-24(25)32)28-26(33)20-9-13-22(35-2)14-10-20/h3,5-14,32H,4,15-18H2,1-2H3,(H,28,33)(H,29,34)

HIDE SMILES / InChI

Molecular Formula C27H30N4O4
Molecular Weight 474.5515
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Darexaban (YM150) is a direct inhibitor of coagulation factor Xa (FXa), discovered by Astellas Pharmaceuticals. FXa is a crucial serine protease in the coagulation cascade, responsible for the cleavage of prothrombin to its active form thrombin, which then converts soluble fibrinogen to insoluble fibrin, activates platelets and causes a formation of a blood clot. Darexaban inhibits factor Xa with a Ki value of 31 nM and shows anticoagulant activity in human plasma. In venous and A-V shunt thrombosis models in rats, darexaban strongly suppressed thrombus formation without affecting bleeding time. Darexaban was investigated in a number of clinical trials for prevention of venous thromboembolism in patients undergoing surgery, prevention of ischaemic events in acute coronary syndrome, prophylaxis of stroke in atrial fibrillation. In 2011 Astellas announced the discontinuation of darexaban because of high competition on anti-FXa drugs market.

Approval Year

PubMed

PubMed

TitleDatePubMed
Discovery of N-[2-hydroxy-6-(4-methoxybenzamido)phenyl]-4- (4-methyl-1,4-diazepan-1-yl)benzamide (darexaban, YM150) as a potent and orally available factor Xa inhibitor.
2011 Dec 8
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:11:43 GMT 2023
Edited
by admin
on Fri Dec 15 16:11:43 GMT 2023
Record UNII
KF322K101S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DAREXABAN
INN   WHO-DD  
INN  
Official Name English
YM150
Code English
TANEXABAN
Common Name English
Darexaban [WHO-DD]
Common Name English
YM-150
Code English
darexaban [INN]
Common Name English
N-(2-HYDROXY-6-(4-METHOXYBENZAMIDO)PHENYL)-4-(4-METHYL-1,4-DIAZEPAN-1-YL)BENZAMIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29750
Created by admin on Fri Dec 15 16:11:43 GMT 2023 , Edited by admin on Fri Dec 15 16:11:43 GMT 2023
Code System Code Type Description
PUBCHEM
9912771
Created by admin on Fri Dec 15 16:11:43 GMT 2023 , Edited by admin on Fri Dec 15 16:11:43 GMT 2023
PRIMARY
DRUG BANK
DB12289
Created by admin on Fri Dec 15 16:11:43 GMT 2023 , Edited by admin on Fri Dec 15 16:11:43 GMT 2023
PRIMARY
SMS_ID
100000126187
Created by admin on Fri Dec 15 16:11:43 GMT 2023 , Edited by admin on Fri Dec 15 16:11:43 GMT 2023
PRIMARY
WIKIPEDIA
DAREXABAN
Created by admin on Fri Dec 15 16:11:43 GMT 2023 , Edited by admin on Fri Dec 15 16:11:43 GMT 2023
PRIMARY
EVMPD
SUB32705
Created by admin on Fri Dec 15 16:11:43 GMT 2023 , Edited by admin on Fri Dec 15 16:11:43 GMT 2023
PRIMARY
EPA CompTox
DTXSID101030146
Created by admin on Fri Dec 15 16:11:43 GMT 2023 , Edited by admin on Fri Dec 15 16:11:43 GMT 2023
PRIMARY
INN
9104
Created by admin on Fri Dec 15 16:11:43 GMT 2023 , Edited by admin on Fri Dec 15 16:11:43 GMT 2023
PRIMARY
FDA UNII
KF322K101S
Created by admin on Fri Dec 15 16:11:43 GMT 2023 , Edited by admin on Fri Dec 15 16:11:43 GMT 2023
PRIMARY
NCI_THESAURUS
C90973
Created by admin on Fri Dec 15 16:11:43 GMT 2023 , Edited by admin on Fri Dec 15 16:11:43 GMT 2023
PRIMARY
CAS
365462-23-3
Created by admin on Fri Dec 15 16:11:43 GMT 2023 , Edited by admin on Fri Dec 15 16:11:43 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY