Dicumarol

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Cat Number

API0232307

CAS Number

66-76-2

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Product Detail Description Scientific Support Customer Q&A

CAS Number

66-76-2

EINECS

200-632-9

Storage

Store at room temperature

Synonyms

Bishydroxycoumarin; Melitoxin; Antitrombosin; Baracoumin; Dicumarine; Acadyl; Acavyl; Dicuman; Dufalone; Kumoran; Temparin; Trombosan

Molecular Formula

C19H12O6

Molecular Weight

336.3

Smiles

C1=CC=C2C(=C1)C(=C(C(=O)O2)CC3=C(C4=CC=CC=C4OC3=O)O)O

Appearance

White to off-white crystalline powder

Melting Point

290-292°C

Boiling Point

392.79°C (Estimate)

Relative Density

1.2864 (Estimate)

General Description

Dicumarol is a naturally occurring anticoagulant, a coumarin derivative first isolated from spoiled sweet clover. Its chemical structure is 3,3′-methylenebis(4-hydroxycoumarin). Dicumarol is a white to off-white crystalline powder that is practically insoluble in water. It is a classic vitamin K antagonist and the historical precursor to modern coumarin anticoagulants.

Mechanism of Action

Dicumarol acts as a competitive inhibitor of vitamin K epoxide reductase (VKORC1), preventing the regeneration of the reduced form of vitamin K, which is essential for the gamma-carboxylation of coagulation factors. This results in the production of inactive forms of factors II, VII, IX, and X, leading to a prolonged prothrombin time and a hypocoagulable state.

Application

Dicumarol was historically used as an oral anticoagulant for the treatment and prevention of thromboembolic disorders. However, its use has been largely superseded by warfarin and other coumarin derivatives due to its unpredictable pharmacokinetics and higher incidence of adverse effects.

Dicumarol, a coumarin compound, potently inhibited pyruvate dehydrogenase kinase 1 (PDK1) in ovarian cancer SKOV3 cells. This shifted glucose metabolism from aerobic glycolysis to oxidative phosphorylation, increased ROS, reduced mitochondrial membrane potential, induced apoptosis, and decreased cell viability. In vivo, dicumarol suppressed xenograft tumor growth. Dicumarol is a novel PDK1 inhibitor that targets the Warburg effect, providing a promising anticancer therapy for ovarian cancer.

Fig. 1 DIC inhibits PDK1 activity in vitro. (Zhang W, et al., 2017)

References

Zhang W, et al. Dicumarol inhibits PDK1 and targets multiple malignant behaviors of ovarian cancer cells. PLoS One. 2017;12(6):e0179672.

Does Dicumarol require protection from light and heat during storage?

Yes, it is sensitive to light and heat. Light causes photodegradation and heat accelerates oxidation of the coumarin ring. Store in light-resistant containers at controlled room temperature (15–25°C).

Is Dicumarol hygroscopic, and how is this managed?

It is slightly hygroscopic. Under high humidity (>70% RH), it may absorb moisture and clump. Storage in tightly sealed containers with desiccant is recommended.

Is Dicumarol 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.