3789 Dicumarol Dicumarol is only found in individuals that have used or taken this drug. It is an oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases. [PubChem] Dicumarol 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. 66-76-2 54676038 C19H12O6 White powder. 290°C 128 mg/L Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101) Dicoumarol is an anticoagulant that competitively inhibits vitamin K, preventing the formation of prothrombin. It does this by inhibiting the enzyme NAD(P)H:quinone oxidoreductase-1, which is required for the reduction of vitamin K to its hydroquinone. Reduced vitamin K is a cofactor needed in the conversion of prothrombin precursor protein to active prothrombin, an essential protein for blood clotting. In addition, inhibition of NAD(P)H:quinone oxidoreductase-1 induces the generation of superoxide anion radicals that inhibit cell growth. Dicoumarol can also potently and reversible inhibit gap junctional intercellular communication, though the precise mechanism is unknown. (L1960, A2994, A2995, A2996, A2997) LD₅₀=233 mg/kg (orally in mice) LD₅₀=250 mg/kg (orally in rats) LD50: 233 mg/kg (Oral, Mouse) (A308) No indication of carcinogenicity to humans (not listed by IARC). Dicoumarol is a mycotoxin of combined plant and fungal origin. It is a derivative of coumarin, a substance made by plants which is transformed in mouldy feeds by a number of species of fungi into active dicoumarol. Dicoumarol is an anticoagulant that is used along with heparin for the treatment of deep venous thrombosis, as well as in biochemical experiments as an inhibitor of reductases. (L1960) Dicoumarol is an anticoagulant. (L1960) Dicoumarol can cause bleeding complications. (L1960) Administration of Vitamin K is the antidote for dicoumarol toxicity. (L1960) 2010-05-05T18:02:55Z 2026-03-26T19:45:26Z Dicumarol C00796 4513 DB00266 true OC1=C(CC2=C(O)C3=C(OC2=O)C=CC=C3)C(=O)OC2=C1C=CC=C2 C19H12O6 InChI=1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2 DOBMPNYZJYQDGZ-UHFFFAOYSA-N 336.295 336.063388116 Exogenous Solid 2.07 HMDB14411 CHEMBL1466 10183330 CHEM002704 DTXSID8021729 NS00001589 4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one