3148 Acenocoumarol Acenocoumarol is a coumarin derivative used as an anticoagulant. Coumarin derivatives inhibit the reduction of vitamin K by vitamin K reductase. This prevents carboxylation of vitamin K-dependent clotting factors, II, VII, XI and X, and interferes with coagulation. Hematocrit, hemoglobin, international normalized ratio and liver panel should be monitored. Patients on acenocoumarol are prohibited from giving blood. 152-72-7 54676537 C19H15NO6 353.089940 White powder. 196-199°C practically insoluble Ingestion (L1817) ; dermal (L1817). Rapidly absorbed orally with greater than 60% bioavailability. Peak plasma levels are attained 1 to 3 hours following oral administration. 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 proteins, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulant proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited. Depression of three of the four vitamin K-dependent coagulation factors (factors II, VII, and X) results in decresed prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots. (A308) 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. LD50: 1470 mg/kg (Oral, Mouse) (T14) LD50: 115 mg/kg (Intraperitoneal, Mouse) (T14) No indication of carcinogenicity to humans (not listed by IARC). Acenocoumarol is an anticoagulant drug derived from coumarin. (L1261) 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 is an anticoagulant and may cause internal bleeding, leading to shock, loss of consciousness, and eventually death. (L1257) 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. The primary antidote to acenocoumarol poisoning is immediate administration of vitamin K1 (initially slow intravenous injections of 10-25 mg repeated all 3-6 hours until normalisation of the prothrombin time; then 10 mg orally four times daily as a "maintenance dose"). It is an extremely effective antidote, provided the poisoning is caught before too much damage has been done to the victim's circulatory system. At high doses acenocoumarol can affect the body for many months, and the antidote must be administered regularly for a long period of time. (L1257) 2009-07-23T18:26:19Z 2026-05-14T17:00:16Z Acenocoumarol 53766 Acenocoumarol DB01418 true CC(=O)CC(C1=CC=C(C=C1)[N+]([O-])=O)C1=C(O)C2=CC=CC=C2OC1=O C19H15NO6 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 VABCILAOYCMVPS-UHFFFAOYSA-N 353.3255 353.089937217 Exogenous Solid 1.98 HMDB15487 CHEMBL397420 10443441 <p>Stoll, W. and Litvan, F.; U.S. Patent 2,648,682; August 11,1953; assigned to J.R. Geigy A.G.,<br /> Switzerland.</p> CHEM002440 DTXSID2022541 NS00041335 4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one 109.41999999999999 94.18479999999998 34.34892877125328 5 5 1 5.793037768490707 -6.825925280097388 -1 3 2.53 -4.52 1.06e-02 g/l