Chemistry:Acenocoumarol

Short description: Anticoagulant

Acenocoumarol

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	X
Routes of administration	Oral
ATC code	B01AA07 (WHO)
Legal status
Legal status	UK: POM (Prescription only)
Pharmacokinetic data
Metabolism	Hepatic
Elimination half-life	8 to 11 hours
Identifiers
IUPAC name (RS)-4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one
CAS Number	152-72-7 Y
PubChem CID	9052
DrugBank	DB01418 Y
ChemSpider	10443441 Y
UNII	I6WP63U32H
KEGG	D07064 Y
ChEBI	CHEBI:53766 Y
ChEMBL	ChEMBL397420 Y
Chemical and physical data
Formula	C19H15NO6
Molar mass	353.330 g·mol−1
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
Melting point	196 to 199 °C (385 to 390 °F)
SMILES CC(=O)CC(C1=CC=C(C=C1)[N+](=O)[O-])C2=C(OC3=CC=CC=C3C2=O)O
InChI 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 Y Key:VABCILAOYCMVPS-UHFFFAOYSA-N Y
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Acenocoumarol is an anticoagulant that functions as a vitamin K antagonist (like warfarin). It is a derivative of coumarin and is generic, so is marketed under many brand names worldwide.

Further reading

• "Aging and oral anticoagulant therapy using acenocoumarol". Blood Coagulation & Fibrinolysis 15 (8): 673–676. October 2004. doi:10.1097/00001721-200412000-00007. PMID 15613922. 
• "[Warfarin or acenocoumarol is better in the anticoagulant treatment of chronic atrial fibrillation?]". Orvosi Hetilap 145 (52): 2619–2621. December 2004. PMID 15724697. 
• "Comparative pharmacokinetics of vitamin K antagonists: warfarin, phenprocoumon and acenocoumarol". Clinical Pharmacokinetics 44 (12): 1227–1246. 2005. doi:10.2165/00003088-200544120-00003. PMID 16372822. 
• "The c.-1639G > A polymorphism of the VKORC1 gene is a major determinant of the response to acenocoumarol in anticoagulated patients". British Journal of Haematology 133 (2): 183–187. April 2006. doi:10.1111/j.1365-2141.2006.06007.x. PMID 16611310. 

External links

• DDB 29202