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SML0074

Sigma-Aldrich

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
EC Number:
205-807-3
MDL number:
MFCD00137816
UNSPSC Code:
12352200
PubChem Substance ID:
329825137
NACRES:
NA.77

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)

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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.

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

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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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
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
Determination of Coumarins in Cosmetics
Application Note, 1128 (2016)
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
Liliane Gschwind et al.
Basic & clinical pharmacology & toxicology, 113(4), 259-265 (2013-05-15)
Vitamin K antagonists (VKAs) are prescribed worldwide and remain the oral anticoagulant of choice. These drugs are characterized by a narrow therapeutic index and a large inter- and intra-individual variability. P-glycoprotein could contribute to this variability. The aim of this
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