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Details

Stereochemistry ACHIRAL
Molecular Formula C27H30N4O4.C4H4O4
Molecular Weight 590.6237
Optical Activity NONE
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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
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

Substance Class Chemical
Record UNII
03RTP2436R
Record Status Validated (UNII)
Record Version