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DICUMAROL Basic information
DICUMAROL Chemical Properties
  • Melting point:290-292 °C(lit.)
  • Boiling point:392.79°C (rough estimate)
  • Density 1.2864 (rough estimate)
  • refractive index 1.4450 (estimate)
  • storage temp. +2C to +8C
  • form Fine Crystalline Powder
  • pka4.20±1.00(Predicted)
  • color White
  • Water Solubility Soluble in aqueous alkaline solutions, organic bases, 0.1 N NaOH (15 mg/ml), Pyridine (50 mg/ml), chloroform (slightly soluble), and benzene (slightly soluble). Insoluble in water, and alcohols.
  • Merck 14,3090
  • EPA Substance Registry System2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy- (66-76-2)
Safety Information
  • Hazard Codes T,N
  • Risk Statements 22-48/25-51/53
  • Safety Statements 37-45-61
  • RIDADR UN 2811 6.1/PG 3
  • WGK Germany 3
  • RTECS GN7875000
  • TSCA Yes
  • HazardClass 6.1(b)
  • PackingGroup III
  • HS Code 29322985
  • ToxicityLD50 orally in rats: 541.6 mg/kg (Rose)
DICUMAROL Usage And Synthesis
  • Chemical Propertieswhite fine crystalline powder
  • Usesanticoagulant
  • DefinitionChEBI: A hydroxycoumarin that is methane in which two hydrogens have each been substituted by a 4-hydroxycoumarin-3-yl group.
  • General DescriptionDicumarol, 3,3'-methylenebis[4-hydroxycoumarin],is a white or creamy white crystalline powderwith a faint, pleasant odor and a slightly bitter taste. It ispractically insoluble in water or alcohol, slightly soluble inchloroform, and dissolved readily by solutions of fixed alkalies.The effects after administration require 12 to 72 hours todevelop and persist for 24 to 96 hours after discontinuance.
  • PharmacokineticsDicoumarol is not completely absorbed in the gastrointestinal tract, often is associated with gastrointestinal discomfort, and is very rarely used clinically. Today, the only coumarin used in the United States is warfarin, but phenprocoumon and acenocomumarol are used in Europe.
  • Clinical UseDicumarol is used alone or as an adjunct to heparin in theprophylaxis and treatment of intravascular clotting. It is usedin postoperative thrombophlebitis, pulmonary embolus, acuteembolic and thrombotic occlusion of peripheral arteries, andrecurrent idiopathic thrombophlebitis. It has no effect on analready-formed embolus but may prevent further intravascularclotting. Because the outcome of acute coronary thrombosisdepends largely on extension of the clot and formation ofmural thrombi in the heart chambers, with subsequent embolization,dicumarol has been used in this condition. It hasalso been administered to arrest impending gangrene afterfrostbite. The dose, after determination of the prothrombinclotting time, is 25 to 200 mg, depending on the size and thecondition of the patient. The drug is given orally in the formof capsules or tablets. On the second day and thereafter, itmay be given in amounts sufficient to maintain the prothrombinclotting time at about 30 seconds. If hemorrhages shouldoccur, a dosage of 50 to 100 mg of menadione sodium bisulfiteis injected, supplemented by a blood transfusion.
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