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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

Pureté

≥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

Certificats d'analyse (COA)

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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
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
M Valdivielso et al.
Journal of the European Academy of Dermatology and Venereology : JEADV, 18(2), 211-215 (2004-03-11)
Cutaneous necrosis is an infrequent but well-documented complication of oral anticoagulants. In the pathogenesis of cutaneous necrosis induced by oral anticoagulants recent hypotheses favour the combined role of local factors and a transient unbalance of coagulation mechanisms leading to an
A M López-Parra et al.
Clinical biochemistry, 46(1-2), 167-169 (2012-08-25)
We have developed a genotyping system to determine the alleles of genes related to interindividual variability in acenocoumarol dosage requirements. This genotyping system is intended for routine clinical use and therefore it is essential that it be simple, fast and
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