Acenocoumarol

Acenocoumarol
Systematic (IUPAC) name

(RS)-4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	X
Routes of administration	Oral
Legal status
Legal status	UK: POM (Prescription only)
Pharmacokinetic data
Metabolism	Hepatic
Biological half-life	8 to 11 hours
Identifiers
CAS Number	152-72-7^Y
ATC code	B01AA07 (WHO)
PubChem	CID 9052
DrugBank	DB01418^Y
ChemSpider	10443441^Y
UNII	I6WP63U32H^Y
KEGG	D07064^Y
ChEBI	CHEBI:53766^Y
ChEMBL	CHEMBL397420^Y
Chemical data
Formula	C₁₉H₁₅NO₆
Molar mass	353.326 g/mol
Chirality	Racemic mixture
SMILES [O-][N+](=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^Y Key:VABCILAOYCMVPS-UHFFFAOYSA-N^Y
(verify)

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.^[1]

References

↑ Drugs.com Drugs.com international listings for acenocoumarol

External links

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.
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.

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

Antiplatelet drugs

Glycoprotein IIb/IIIa inhibitors	Abciximab Eptifibatide Tirofiban Roxifiban Orbofiban

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 Receptor antagonists 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

Direct thrombin (IIa) inhibitors

Other

Thrombolytic drugs/
fibrinolytics

Non-medicinal

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Types of coumarins

Aglycones

O-Methylated	Fraxetin Herniarin (7-O-Methylumbelliferone) Osthol Scopoletin (6-Methoxyumbelliferone)

glycosides

Aesculin (Esculetin 6-O-glucoside)
Fraxin (Fraxetin glucoside)
Skimmin (Umbelliferone 7-O-glucoside)
Scopolin
Umbelliferone 7-apiosylglucoside

derivatives

Furanocoumarins

Aglycones

Angelicin
Marmesin
Psoralen
Vaginol
Xanthotoxol (8-Hydroxypsoralen)

O-Methylated	Bergapten (5-methoxypsoralen) Isopimpinellin (5,8-Dimethoxypsoralene) Methoxsalen (8-Methoxypsoralen) Trioxsalen (2,5,9-Trimethylpsoralen)

Furanocoumarin glycosides

Apterin (vaginol glucoside)

Meroterpene furanocoumarin ether

Oligomers

Dicoumarol

Synthetic

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