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Merck
CN

SML2845

Betrixaban

≥98% (HPLC)

Synonym(s):

MK-4448, MLN1021, N-(5-Chloro-2-pyridinyl)-2-[[4-[(dimethylamino)iminomethyl]benzoyl]amino]-5-methoxybenzamide, N-(5-Chloropyridin-2-yl)-2-(4-(N,N-dimethylcarbamimidoyl)benzamido)-5-methoxybenzamide, PRT-054021, PRT054021

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About This Item

Empirical Formula (Hill Notation):
C23H22ClN5O3
CAS Number:
330942-05-7
Molecular Weight:
451.91
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD16038040

Key Documents

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InChI

1S/C23H22ClN5O3/c1-29(2)21(25)14-4-6-15(7-5-14)22(30)27-19-10-9-17(32-3)12-18(19)23(31)28-20-11-8-16(24)13-26-20/h4-13,25H,1-3H3,(H,27,30)(H,26,28,31)

SMILES string

ClC1=CN=C(C=C1)NC(C2=C(NC(C3=CC=C(C(N(C)C)=N)C=C3)=O)C=CC(OC)=C2)=O

InChI key

XHOLNRLADUSQLD-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Betrixaban is an orally active, active site-targeting, highly potent and selective factor Xa (fXa) inhibitor (IC50 = 1.5 nM; Ki = 117 pM) with much reduced plasma kallikrein inhibitory activity (IC50 = 6.3 μM) and little potency against thrombin, trypsin, t-PA, aPC or plasmin inhibition (IC50 >10 μM). Betrixaban exhibits good pharmacokinetic properties and anticoagulant efficacy against various thromboembolism (VTE) events in vivo.
Orally active, active site-targeting, highly potent and selective factor Xa (fXa) inhibitor with anticoagulant efficacy against thromboembolism (VTE) events in vivo.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

hcodes

H302,H373

Hazard Classifications

Acute Tox. 4 Oral - STOT RE 2

target_organs

Blood

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000428646
0000428646
0000423139
0000101966
0000101967

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Penglie Zhang et al.
Bioorganic & medicinal chemistry letters, 19(8), 2179-2185 (2009-03-20)
Systematic SAR studies of in vitro factor Xa inhibitory activity around compound 1 were performed by modifying each of the three phenyl rings. A class of highly potent, selective, efficacious and orally bioavailable direct factor Xa inhibitors was discovered. These
Emmanuel J Favaloro et al.
Seminars in thrombosis and hemostasis, 41(2), 208-227 (2015-02-24)
A new generation of antithrombotic agents has recently emerged. These provide direct inhibition of either thrombin (factor IIa [FIIa]) or FXa, and are increasingly replacing the classical anticoagulants (heparin and coumarins such as warfarin) in clinical practice for a variety
Meyer Michel Samama et al.
Clinics in laboratory medicine, 34(3), 503-517 (2014-08-30)
New oral factor Xa inhibitors are intended to progressively substitute the oral vitamin K antagonists and parenteral indirect inhibitors of factor Xa in the prevention and treatment of venous and arterial thromboembolic episodes. This article focuses on the main clinical
Menno V Huisman et al.
European heart journal supplements : journal of the European Society of Cardiology, 20(Suppl E), E12-E15 (2018-07-07)
Venous thromboembolism (VTE) in acute medically ill patients is a leading cause of in-hospital morbidity and mortality. A majority of these VTE events occur post-discharge, and patients remain at increased VTE risk for up to 3 months post-discharge. Recent clinical trials
Romain Siriez et al.
Thrombosis and haemostasis, 118(7), 1203-1214 (2018-06-12)
Betrixaban is a novel direct oral factor Xa inhibitor approved by the Food and Drug Administration for prophylaxis of venous thromboembolism in adult patients hospitalized for an acute illness at risk for thromboembolic complications. Assessment of the anti-coagulant effect of
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