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USP

Acenocoumarol

United States Pharmacopeia (USP) Reference Standard

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:
Molecular Weight:
353.33
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:

manufacturer/tradename

USP

application(s)

pharmaceutical (small molecule)

format

neat

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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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

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

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

USP issued SDS can be found here.
Sales restrictions may apply.

pictograms

Exclamation mark

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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[The potentiation of the anticoagulant effect of acenocoumarol by cefonicid].
M Puente García et al.
Revista clinica espanola, 199(9), 620-621 (1999-11-24)
CYP2C9 and oral anticoagulation therapy with acenocoumarol and warfarin: similarities yet differences.
Harumi Takahashi et al.
Clinical pharmacology and therapeutics, 75(5), 376-380 (2004-04-30)
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
Pierre Delanaye et al.
BMC nephrology, 15, 145-145 (2014-09-06)
Matrix Gla protein (MGP) is known to act as a potent local inhibitor of vascular calcifications. However, in order to be active, MGP must be phosphorylated and carboxylated, with this last process being dependent on vitamin K. The present study
Non-vitamin K antagonist oral anticoagulants: an appeal for consensus on terminology.
Gregory Y H Lip et al.
Chest, 145(5), 1177-1178 (2014-05-07)

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