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Details

Stereochemistry ACHIRAL
Molecular Formula C27H30N4O4.C4H4O4
Molecular Weight 590.6237
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of DAREXABAN MALEATE

SMILES

OC(=O)\C=C/C(O)=O.COC1=CC=C(C=C1)C(=O)NC2=CC=CC(O)=C2NC(=O)C3=CC=C(C=C3)N4CCCN(C)CC4

InChI

InChIKey=WHMPMUVISXATBH-BTJKTKAUSA-N
InChI=1S/C27H30N4O4.C4H4O4/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;5-3(6)1-2-4(7)8/h3,5-14,32H,4,15-18H2,1-2H3,(H,28,33)(H,29,34);1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI

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

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

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 Tue Oct 22 15:42:56 UTC 2019
Edited
by admin
on Tue Oct 22 15:42:56 UTC 2019
Record UNII
03RTP2436R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DAREXABAN MALEATE
Common Name English
N-(3-HYDROXY-2-((4-(4-METHYL-1,4-DIAZEPAN-1-YL)BENZOYL)AMINO)PHENYL)-4-METHOXYBENZAMIDE MALEIC ACID
Systematic Name English
DAREXABAN MALEATE [JAN]
Common Name English
YM-150 MALEIC ACID
Code English
Code System Code Type Description
PUBCHEM
49843900
Created by admin on Tue Oct 22 15:42:56 UTC 2019 , Edited by admin on Tue Oct 22 15:42:56 UTC 2019
PRIMARY
CAS
365462-24-4
Created by admin on Tue Oct 22 15:42:56 UTC 2019 , Edited by admin on Tue Oct 22 15:42:56 UTC 2019
PRIMARY
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ACTIVE MOIETY