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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
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
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Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

DMSO, heptane and xylene: ≥17 mg/mL

originator

Novartis

storage temp.

−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

InChI key

VABCILAOYCMVPS-UHFFFAOYSA-N

Gene Information

human ... VKORC1(79001)

Application

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.
Acenocoumarol has been used as a standard for the determination of coumarins in cosmetics.

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.
Warfarin analog; anticoagulant; inhibitor of Vit K epoxide reductase
Acenocoumarol is effective against thromboembolic disorders.

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.

wgk

WGK 3

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

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000427524
0000427525
0000427525
0000427524
0000420842

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Articles

Bioactive Molecules for Immunology Research

Bioactive small molecules for immune system signaling target identification/validation and antibiotics, antivirals, and antifungals offered.

Antonio J Carcas et al.
Trials, 13, 239-239 (2012-12-15)
Hemorrhagic events are frequent in patients on treatment with antivitamin-K oral anticoagulants due to their narrow therapeutic margin. Studies performed with acenocoumarol have shown the relationship between demographic, clinical and genotypic variants and the response to these drugs. Once the
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
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