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.



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.


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.


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

Chemical & physical properties

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


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

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All information used for the content comes from verified sources (recognised institutions, experts, studies by renowned universities). We attach great importance to the qualification of the authors and the scientific background of the information. Thus, we ensure that our research is based on scientific findings.
Markus Falkenstätter, BSc

Markus Falkenstätter, BSc

Markus Falkenstätter is a writer on pharmaceutical topics in Medikamio's medical editorial team. He is in the last semester of his pharmacy studies at the University of Vienna and loves scientific work in the field of natural sciences.

Mag. pharm. Stefanie Lehenauer

Mag. pharm. Stefanie Lehenauer

Stefanie Lehenauer has been a freelance writer for Medikamio since 2020 and studied pharmacy at the University of Vienna. She works as a pharmacist in Vienna and her passion is herbal medicines and their effects.

The content of this page is an automated and high-quality translation from DeepL. You can find the original content in German here.


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