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SML0074

Sigma-Aldrich

Acenocoumarol

≥98% (HPLC)

Synonym(e):

3-(α-Acetonyl-p-nitrobenzyl)-4-hydroxy-cumarin

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About This Item

Empirische Formel (Hill-System):
C19H15NO6
CAS-Nummer:
152-72-7
Molekulargewicht:
353.33
EG-Nummer:
205-807-3
MDL-Nummer:
MFCD00137816
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329825137
NACRES:
NA.77

Assay

≥98% (HPLC)

Form

powder

Farbe

white to tan

Löslichkeit

DMSO, heptane and xylene: ≥17 mg/mL

Ersteller

Novartis

Lagertemp.

−20°C

SMILES String

CC(=O)CC(c1ccc(cc1)[N+]([O-])=O)C2=C(O)c3ccccc3OC2=O

InChI

1S/C19H15NO6/c1-11(21)10-15(12-6-8-13(9-7-12)20(24)25)17-18(22)14-4-2-3-5-16(14)26-19(17)23/h2-9,15,22H,10H2,1H3

InChIKey

VABCILAOYCMVPS-UHFFFAOYSA-N

Angaben zum Gen

human ... VKORC1(79001)

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Anwendung

Acenocoumarol has been used as a standard for the determination of coumarins in cosmetics.
Acenocoumarol was used to study the role of P-glycoprotein in transport of oral vitamin K in Caco-2 cells and as an LC/MS standard.

Biochem./physiol. Wirkung

Acenocoumarol is a warfarin analog, an anticoagulant that inhibits Vitamin K epoxide reductase. This results in depletion of the reduced form of vitamin K (vitamin KH2), limiting the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S, resulting in decreased prothrombin levels and the amount of thrombin generated.
Acenocoumarol is effective against thromboembolic disorders.

Leistungsmerkmale und Vorteile

This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Saurabh Singh Rathore et al.
PloS one, 7(5), e37844-e37844 (2012-05-26)
To develop a population specific pharmacogenetic acenocoumarol dosing algorithm for north Indian patients and show its efficiency in dosage prediction. Multiple and linear stepwise regression analyses were used to include age, sex, height, weight, body surface area, smoking status, VKORC1
Juan J Cerezo-Manchado et al.
Thrombosis and haemostasis, 109(1), 146-153 (2012-12-01)
Acenocoumarol is a commonly prescribed anticoagulant drug for the prophylaxis and treatment of venous and arterial thromboembolic disorders in several countries. In counterpart of warfarin, there is scarce information about pharmacogenetic algorithms for steady acenocoumarol dose estimation. The aim of
Determination of Coumarins in Cosmetics
Application Note, 1128 (2016)
Rianne M F van Schie et al.
Pharmacogenomics, 13(11), 1239-1245 (2012-08-28)
To evaluate the performance of the European Pharmacogenetics of Anticoagulant Therapy (EU-PACT) acenocoumarol dose algorithms in an independent data set. The EU-PACT trial investigates the added value of pretreatment genotyping for use of warfarin, phenprocoumon and acenocoumarol. External validation was
Alberto M Borobia et al.
PloS one, 7(7), e41360-e41360 (2012-08-23)
Appropriate dosing of coumarins is difficult to establish, due to significant inter-individual variability in the dose required to obtain stable anticoagulation. Several genetic and other clinical factors have been associated with the coumarins dose, and some pharmacogenetic-guided dosing algorithms for
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