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SML0074 Sigma-Aldrich

Acenocoumarol

≥98% (HPLC)

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

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Properties

Related Categories A-AM, Anticoagulants, Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
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)

Description

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.

Packaging

10, 50 mg in glass bottle

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.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Target organs 
Respiratory system
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
GN4900000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Anticoagulants

Pulmonary arterial hypertension (PAH) is characterized as a progressive, incurable disease and its treatment remains elusive.1 The mean survival rate is often less than 4 years and the median surviva...
Sami Barghshoon
BioFiles v7 n5, 2012, 25–26
Keywords: Anticoagulants, Cardiovascular, PAGE

Discover Bioactive Small Molecules for Immunology Research

The immune system is a complex network to detect and defend against non-self pathogenic agents, such as disease-causing viruses, bacteria, and other microorganisms. Various signaling pathways contrib...
Keywords: Antibiotics, Antifungals, Antivirals, Apoptosis, Bioactive small molecules, Cell signaling, Diabetes, Diseases, Immunology, Inflammation

Peer-Reviewed Papers
15

References

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