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Merck
CN

SML0074

Acenocoumarol

≥98% (HPLC)

Synonym(s):

(±)-Acenocoumarin, 3-(α-Acetonyl-p-nitrobenzyl)-4-hydroxy-coumarin

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About This Item

Empirical Formula (Hill Notation):
C19H15NO6
CAS Number:
152-72-7
Molecular Weight:
353.33
NACRES:
NA.77
PubChem Substance ID:
329825137
UNSPSC Code:
12352200
EC Number:
205-807-3
MDL number:
MFCD00137816

Key Documents

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Product Name

Acenocoumarol, ≥98% (HPLC)

InChI key

VABCILAOYCMVPS-UHFFFAOYSA-N

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

SMILES string

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

assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

DMSO, heptane and xylene: ≥17 mg/mL

originator

Novartis

storage temp.

−20°C

Quality Level

100

Gene Information

human ... VKORC1(79001)

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Application

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 Actions

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.
Warfarin analog; anticoagulant; inhibitor of Vit K epoxide reductase

Features and Benefits

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

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
0000427524
0000427525
0000427525
0000427524
0000420842

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Branislav V Bajkin et al.
Journal of the American Dental Association (1939), 143(7), 771-776 (2012-07-04)
The authors conducted a study to evaluate the effect of combined oral anticoagulant-aspirin therapy on postoperative bleeding in patients undergoing tooth extractions. A total of 213 patients were divided into three groups of 71 participants each. Patients in group A
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
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
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
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
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