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SML2844

Sigma-Aldrich

Rivaroxaban

≥98% (HPLC)

Synonym(s):

(S)-Rivaroxaban, (S)-5-Chloro-N-{[2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]oxazolidin-5-yl]methyl} thiophene-2-carboxamide, 5-Chloro-N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide, BAY 59-7939, BAY-59-7939, BAY59-7939, 5-Chloro-N-[[(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-2-thiophenecarboxamide

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About This Item

Empirical Formula (Hill Notation):
C19H18ClN3O5S
CAS Number:
366789-02-8
Molecular Weight:
435.88
MDL number:
MFCD11974010
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -34 to -44, c = 0.3 in DMSO

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

InChI

1S/C19H18ClN3O5S/c20-16-6-5-15(29-16)18(25)21-9-14-10-23(19(26)28-14)13-3-1-12(2-4-13)22-7-8-27-11-17(22)24/h1-6,14H,7-11H2,(H,21,25)/t14-/m0/s1

InChI key

KGFYHTZWPPHNLQ-AWEZNQCLSA-N

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Biochem/physiol Actions

Rivaroxaban is an orally active, active site-targeting, highly potent and selective factor Xa (FXa) inhibitor (IC50 = 0.7 nM; no activity against thrombin, trypsin, plasmin, FVIIa, FIXa, FXIa, urokinase, or activated protein C up to 20 μM) with good anticoagulant activity in vitro (dose for doubling fibrin formation time = 230/300 nM in human/rat plasma) and antithrombotic efficacy in vivo (ED50 = 1 mg/kg i.v. or 5 mg/kg p.o. by rat arteriovenous shunt model).

Pictograms

Environment
GHS09

Hazard Statements

H411

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Chronic 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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In vitro inhibition of thrombin generation, after tissue factor pathway activation, by the oral, direct factor Xa inhibitor rivaroxaban.
G T Gerotziafas et al.
Journal of thrombosis and haemostasis : JTH, 5(4), 886-888 (2007-03-29)
Faisal Imam et al.
Cardiovascular toxicology, 20(3), 281-290 (2019-11-07)
Sunitinib (SUN) is an oral tyrosine kinase inhibitor approved in 2006 as a first-line treatment for metastatic renal cell cancer. However, weak selectivity to kinase receptors and cardiotoxicity have limited the use of sunitinib. Rivaroxaban (RIVA) is a Factor Xa
Tobias Petzold et al.
Circulation research, 126(4), 486-500 (2019-12-21)
A reduced rate of myocardial infarction has been reported in patients with atrial fibrillation treated with FXa (factor Xa) inhibitors including rivaroxaban compared with vitamin K antagonists. At the same time, low-dose rivaroxaban has been shown to reduce mortality and
Bart J Biemond et al.
Thrombosis and haemostasis, 97(3), 471-477 (2007-03-06)
Current anticoagulant therapies for the prevention and treatment of thromboembolic disorders have many drawbacks: vitamin K antagonists interact with food and drugs and require frequent laboratory monitoring, and heparins require parenteral administration. Oral rivaroxaban (BAY 597939) is a new, highly
Susanne Roehrig et al.
Journal of medicinal chemistry, 48(19), 5900-5908 (2005-09-16)
Despite recent progress in antithrombotic therapy, there is still an unmet medical need for safe and orally available anticoagulants. The coagulation enzyme Factor Xa (FXa) is a particularly promising target, and recent efforts in this field have focused on the
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