Phenprocoumon

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Cat Number

API0232306

CAS Number

435-97-2

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Product Detail Description Scientific Support Customer Q&A

CAS Number

435-97-2

EINECS

207-108-9

Storage

Store at room temperature

Synonyms

Phenprocoumarol; Phenprocoumarole; 4-Hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one; Liquamar; Marcumar; Marcoumar; Fencumar

Molecular Formula

C18H16O3

Molecular Weight

280.3

Smiles

CCC(C1=CC=CC=C1)C2=C(C3=CC=CC=C3OC2=O)O

Appearance

White crystalline powder

Melting Point

173-176°C

Boiling Point

419.5°C at 760 mmHg

Relative Density

1.261

General Description

Phenprocoumon is a synthetic coumarin derivative, specifically 4-hydroxy-3-(1-phenylpropyl)-2H-1-benzopyran-2-one, which functions as a long-acting oral anticoagulant. It is a white crystalline powder that is practically insoluble in water. The molecule is a racemic mixture of two enantiomers, both of which are pharmacologically active.

Mechanism of Action

Phenprocoumon acts by inhibiting the enzyme vitamin K epoxide reductase (VKORC1) in the liver, preventing the regeneration of reduced vitamin K. This blocks the gamma-carboxylation of glutamic acid residues on coagulation factors II, VII, IX, and X, rendering them biologically inactive. The resulting reduction in functional clotting factors produces a prolonged anticoagulant effect.

Application

Phenprocoumon is indicated for the prophylaxis and treatment of venous thromboembolism (VTE), including deep vein thrombosis and pulmonary embolism, and for the prevention of thromboembolic events in patients with atrial fibrillation or mechanical heart valves. It has a longer half-life than warfarin, allowing for once-daily dosing.

The AXADIA-AFNET 8 trial randomized 97 patients with atrial fibrillation on hemodialysis to apixaban 2.5 mg BID or phenprocoumon (VKA). The composite primary safety outcome occurred in 45.8% vs 51.0% (HR 0.93, 95% CI 0.53-1.65, P for noninferiority = 0.157). Primary efficacy outcomes occurred in 20.8% vs 30.6%. No significant differences were observed in individual outcomes (all-cause mortality 18.8% vs 24.5%, major bleeding 10.4% vs 12.2%). Larger trials are needed to determine the optimal anticoagulation regimen in this high-risk population.

Fig. 1 Cumulative incidence of the composite primary safety and efficacy outcome. (Reinecke H, et al., 2023)

References

Reinecke H, et al. A Randomized Controlled Trial Comparing Apixaban With the Vitamin K Antagonist Phenprocoumon in Patients on Chronic Hemodialysis: The AXADIA-AFNET 8 Study. Circulation. 2023;147(4):296-309.

Does Phenprocoumon require protection from light and moisture during storage?

Yes, it is sensitive to both light and moisture. Light causes photodegradation and moisture promotes hydrolysis of the coumarin ring. Store in light-resistant, tightly sealed containers with desiccant.

What is the recommended storage temperature for Phenprocoumon?

Store at controlled room temperature (15–25°C). Avoid excessive heat above 30°C, which accelerates degradation and discoloration.

Is Phenprocoumon stable in tablet formulations with standard excipients?

Yes, when formulated with moisture-protective packaging.

How is the impurity 4-hydroxycoumarin (a hydrolysis product) monitored?

This degradation product is specifically quantified using a stability-indicating HPLC method, ensuring it remains within pharmacopoeial limits.