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SML0074

Sigma-Aldrich

Acenocoumarol

≥98% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C19H15NO6
Numéro CAS:
152-72-7
Poids moléculaire :
353.33
Numéro CE :
205-807-3
Numéro MDL:
MFCD00137816
Code UNSPSC :
12352200
ID de substance PubChem :
329825137
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Essai

≥98% (HPLC)

Forme

powder

Couleur

white to tan

Solubilité

DMSO, heptane and xylene: ≥17 mg/mL

Auteur

Novartis

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

VABCILAOYCMVPS-UHFFFAOYSA-N

Informations sur le gène

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302,H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
081M4723V

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Consulter la Bibliothèque de documents

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
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
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
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
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