Acenocoumarol: Difference between revisions

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	\| IUPAC_name = (''RS'')-4-hydroxy-3--2''H''-chromen-2-one		\| IUPAC_name = (''RS'')-4-hydroxy-3--2''H''-chromen-2-one
			\| image = Acenocoumarol.svg
	\| image = Acenocumarol Structural Formulae of both Enantiomers.png
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Revision as of 02:13, 11 December 2011

Pharmaceutical compound

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--2H-chromen-2-one
CAS Number	152-72-7
PubChem CID	9052
DrugBank	DB01418
ChemSpider	10443441
UNII	I6WP63U32H
KEGG	D07064
ChEBI	CHEBI:53766
ChEMBL	ChEMBL397420
CompTox Dashboard (EPA)	DTXSID2022541
ECHA InfoCard	100.005.281
Chemical and physical data
Formula	C₁₉H₁₅NO₆
Molar mass	353.326 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES (=O)c1ccc(cc1)C(CC(C)=O)C\2=C(/O)c3ccccc3OC/2=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 Key:VABCILAOYCMVPS-UHFFFAOYSA-N
(verify)

Acenocoumarol is an anticoagulant that functions as a vitamin K antagonist (like warfarin). It is a derivative of coumarin and is marketed under the brand names Sintrom and Sinthrome.

Dosage

Research in the RECAVA network has discovered that two acquired factors (age and body mass index) and three genetic polymorphisms (genes VKORC1, CYP2C9 and CYP4F2) are useful to establish the right dosage. Acenocoumarol is contraindicated during pregnancy.

External links

Diseases Database (DDB): 29202
Cesar J, García-Avello A, Navarro J, Herraez M (2004). "Aging and oral anticoagulant therapy using acenocoumarol". Blood Coagul Fibrinolysis. 15 (8): 673–6. doi:10.1097/00001721-200412000-00007. PMID 15613922.{{cite journal}}: CS1 maint: multiple names: authors list (link)
Lengyel M; SPORTIF-III Altanulmány Vizsgálói (2004). "Warfarin or acenocoumarol is better in the anticoagulant treatment of chronic atrial fibrillation?". Orv Hetil. 145 (52): 2619–21. PMID 15724697.
Ufer M (2005). "Comparative pharmacokinetics of vitamin Kd antagonists: warfarin, phenprocoumon and acenocoumarol". Clin Pharmacokinet. 44 (12): 1227–46. doi:10.2165/00003088-200544120-00003. PMID 16372822.
Montes R, Ruiz de Gaona E, Martínez-González M, Alberca I, Hermida J (2006). "The c.-1639G > A polymorphism of the VKORC1 gene is a major determinant of the response to acenocoumarol in anticoagulated patients". Br J Haematol. 133 (2): 183–7. doi:10.1111/j.1365-2141.2006.06007.x. PMID 16611310.{{cite journal}}: CS1 maint: multiple names: authors list (link)

Antithrombotics (thrombolytics, anticoagulants and antiplatelet drugs) (B01)

Antiplatelet drugs

Glycoprotein IIb/IIIa inhibitors	Abciximab Eptifibatide Orbofiban Roxifiban Sibrafiban Tirofiban
ADP receptor/P2Y₁₂ inhibitors	Thienopyridines Clopidogrel Prasugrel Ticlopidine Nucleotide/nucleoside analogs Cangrelor Elinogrel Ticagrelor
Prostaglandin analogue (PGI2)	Beraprost Iloprost Prostacyclin Treprostinil
COX inhibitors	Acetylsalicylic acid/Aspirin Aloxiprin Carbasalate calcium Indobufen Triflusal
Thromboxane inhibitors	Thromboxane synthase inhibitors Dipyridamole (+ aspirin) Picotamide Terbogrel Receptor antagonists Terbogrel Terutroban
Phosphodiesterase inhibitors	Cilostazol Dipyridamole Triflusal
Other	Cloricromen Ditazole Vorapaxar

Anticoagulants

Vitamin K antagonists
(inhibit II, VII, IX, X)

Factor Xa inhibitors
(with some II inhibition)

Heparin group/ glycosaminoglycans/ (bind antithrombin)	Low-molecular-weight heparin Bemiparin Certoparin Dalteparin Enoxaparin Nadroparin Parnaparin Reviparin Tinzaparin Oligosaccharides Fondaparinux Idraparinux Heparinoids Danaparoid Dermatan sulfate Sulodexide
Direct Xa inhibitors ("xabans")	Apixaban Betrixaban Darexaban Edoxaban Otamixaban Rivaroxaban