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QuickView for Acenocoumarol (compound)

Name: Acenocoumarol
PubChem Compound ID: 181809
Description: A coumarin that is used as an anticoagulant. Its actions and uses are similar to those of WARFARIN. (From Martindale, The Extra Pharmacopoeia, 30th ed, p233)
Molecular formula: C19H15NO6
Molecular weight: 353.326 g/mol
66556-77-2; CAS-152-72-7; NCGC00016414-01; ZINC00538563
Name: Acenocoumarol
Name (isomeric): DB01418
Drug Type: small molecule
Description: A coumarin that is used as an anticoagulant. Its actions and uses are similar to those of WARFARIN. (From Martindale, The Extra Pharmacopoeia, 30th ed, p233)
Acenocoumarolum [INN-latin]; Nitrophenylacetylethyl-4-hydroxycoumarine; Nicoumalone; Acenocoumarin; Nicumalon; Nitrowarfarin; Nitrovarfarian
Brand: Sincoumar, Sinthrome, Sintrom, Sinthrom, Ascumar, Mini-sintrom, Syncumar, Neositron, Syntrom, Syncoumar, Sinkumar, Zotil
Category: Anticoagulants, Coumarin and Indandione Derivatives
CAS number: 152-72-7
Indication: For the treatment and prevention of thromboembolic diseases. More specifically, it is indicated for the for the prevention of cerebral embolism, deep vein thrombosis, pulmonary embolism, thromboembolism in infarction and transient ischemic attacks. It is used for the treatment of deep vein thrombosis and myocardial infarction.
Acenocoumarol inhibits the reduction of vitamin K by vitamin K reductase. This prevents carboxylation of certain glutamic acid residues near the N-terminals of clotting factors II, VII, IX and X, the vitamin K-dependent clotting factors. Glutamic acid carboxylation is important for the interaction between these clotting factors and calcium. Without...
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Mechanism of Action:
Acenocoumarol inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). As vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent clotting factors, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulan...
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Absorption: Rapidly absorbed orally with greater than 60% bioavailability. Peak plasma levels are attained 1 to 3 hours following oral administration.
Protein binding: 98.7% protein bound, mainly to albumin
Biotransformation: Extensively metabolized in the liver via oxidation forming two hydroxy metabolites and keto reduction producing two alcohol metabolites. Reduction of the nitro group produces an amino metabolite which is further transformed to an acetoamido metabolite. Metabolites do not appear to be pharmacologically active.
Route of elimination: Mostly via the kidney as metabolites
Half Life: 8 to 11 hours.
Toxicity: The onset and severity of the symptoms are dependent on the individual's sensitivity to oral anticoagulants, the severity of the overdosage, and the duration of treatment. Bleeding is the major sign of toxicity with oral anticoagulant drugs. The most frequent symptoms observed are: cutaneous bleeding (80%), haematuria (with renal colic) (52%), haematomas, gastrointestinal bleeding, haematemesis, uterine bleeding, epistaxis, gingival bleeding and bleeding into the joints. Further symptoms include tachycardia, hypotension, peripheral circulatory disorders due to loss of blood, nausea, vomiting, diarrhoea and abdominal pains.
Affected organisms: Humans and other mammals
Food interaction:
High doses of vitamin A, C, E and K (e.g. avocado, green vegetables)
Drug interaction:
ThiabendazoleThe strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Acenocoumarol by decreasing Acenocoumarol metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Acenocoumarol if Thiabendazole is initiated, discontinued or dose changed.
PhenylbutazoneThe NSAID, phenylbutazone, may increase the anticoagulant effect of acenocoumarol.
NorfloxacinThe quinolone antibiotic, norfloxacin, may increase the anticoagulant effect of acenocoumarol.
GemcitabineGemcitabine may increase the anticoagulant effect of acenocoumarol.
TolmetinIncreased risk of bleeding. Monitor for signs and symptoms of bleeding.
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