Phenprocoumon

Phenprocoumon
ATC Code B01AA04
Formula C18H16O3
Molar Mass (g·mol−1) 280,32
Physical State solid
Melting Point (°C) 179–180
PKS Value 4,20
CAS Number 435-97-2
PUB Number 54680692
Drugbank ID DB00946
Solubility sparingly soluble in water

Basics

Phenprocoumon is a long-acting oral anticoagulant and a derivative of coumarin. It is a vitamin K antagonist that inhibits coagulation by blocking the synthesis of clotting factors II, VII, IX, and X. It is used for prophylaxis and treatment of thromboembolic diseases (thrombosis/pulmonary embolism) and for prophylaxis of myocardial infarction in ventricular fibrillation. It is the standard coumarin used in Germany. It is administered in the form of peroral and parenteral preparations.

Pharmacology

Pharmacodynamics

Phenprocoumon inhibits the enzyme vitamin K reductase, resulting in a deficiency of the reduced form of vitamin K (vitamin K2). Because vitamin K is a cofactor for the carboxylation of vitamin K-dependent proteins, this limits the gamma carboxylation and subsequent activation of vitamin K-dependent coagulation proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X, as well as the anticoagulant proteins C and S, is inhibited. This leads to a decreased prothrombin level which in turn leads to a decrease in thrombin. Thrombin is instrumental in the cross-linking of platelets. This significantly reduces the likelihood of thromboembolic events.

Pharmacokinetics

Bioavailability is close to 100%. Protein binding is 99%. Phenprocoumon is metabolized by hepatic microsomal enzymes (mainly CYP2C9 ) to inactive hydroxylated metabolites and by reductases to reduced metabolites. The elimination half-life is between 5 and 6 days.

Drug Interactions

In general, combination with other anticoagulants should be avoided as this may result in a severe bleeding tendency.

Toxicity

Side effects

Common side effects:

  • Hematomas after injuries
  • blood in urine
  • Nosebleeds
  • Bleeding gums

In rare cases, liver inflammation and dangerous brain bleeding may also occur.

Other less common side effects:

  • Hair loss
  • decrease in bone density
  • gray discoloration of the skin
  • urticaria
  • skin necrosis

Toxicological data

LD50 (rat, oral): 200 mg-kg-1

Sources

  • Drugbank
  • PubChem
  • Aktories, Förstermann, Hofmann, Starke: Allgemeine und spezielle Pharmakologie und Toxikologie, Elsvier, 2017
Markus Falkenstätter

Markus Falkenstätter
Author

Markus Falkenstätter ist Autor zu pharmazeutischen Themen in der Medizin-Redaktion von Medikamio. Er befindet sich im letzten Semester seines Pharmaziestudiums an der Universität Wien und liebt das wissenschaftliche Arbeiten im Bereich der Naturwissenschaften.

Mag. pharm Stefanie Lehenauer

Mag. pharm Stefanie Lehenauer
Lector

Stefanie Lehenauer ist seit 2020 freie Autorin bei Medikamio und studierte Pharmazie an der Universität Wien. Sie arbeitet als Apothekerin in Wien und ihre Leidenschaft sind pflanzliche Arzneimittel und deren Wirkung.

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