Phenprocoumon

CAS No:
435-97-2 Categories: , ,
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Product Details:

  • CAS No: 435-97-2
  • AHFC code:
  • Synonyms: Fenprocumone [DCIT] Phenprocoumarol Phenprocoumarole Phenprocoumone Phenprocumone
  • ATC Code: B01AA04
  • Chemical Formula: C30H34O13
  • Molecular Weight: 280.3178
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB00946 (APRD00228)
  • SMILES: CCC(C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC=C2
  • InChl: DQDAYGNAKTZFIW-UHFFFAOYSA-N
  • PubChem: 9908
  • IUPAC: 4-hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one

Additional Details

Indication:
Used for the prevention and treatment of thromboembolic disease including venous thrombosis, thromboembolism, and pulmonary embolism as well as for the prevention of ischemic stroke in patients with atrial fibrillation (AF).
Pharmacodynamics:
Phenprocoumon, a coumarin anticoagulant, thins the blood by antagonizing vitamin K which is required for the production of clotting factors in the liver. Anticoagulants such as phenprocoumon have no direct effect on an established thrombus, nor do they reverse ischemic tissue damage (damage caused by an inadequate blood supply to an organ or part of the body). However, once a thrombus has occurred, the goal of anticoagulant treatment is to prevent further extension of the formed clot and prevent secondary thromboembolic complications which may result in serious and possibly fatal sequelae.
Mode of Action:
Phenprocoumon 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 decreased prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots.
Metabolism:
Phenprocoumon is stereoselectively metabolized by hepatic microsomal enzymes (cytochrome P-450) to inactive hydroxylated metabolites (predominant route) and by reductases to reduced metabolites. Cytochrome P450 2C9 is the principal form of human liver P-450 responsible for metabolism.
Toxicity:
50=500 mg/kg. Symptoms of overdose includes suspected or overt abnormal bleeding (e.g., appearance of blood in stools or urine, hematuria, excessive menstrual bleeding, melena, petechiae, excessive bruising or persistent oozing from superficial injuries).
General Reference:
Products currently covered by valid US Patents are offered for R&D use in accordance with 35 USC 271(e)+A13(1). Any patent infringement and resulting liability is solely at buyer risk.

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