Dicumarol

Structural formula
General
Non-proprietary name	Dicumarol
other names	Dicoumarol; 3,3'-methylenebis (4-hydroxycoumarin); Melitoxin; Dufalon; Dicoumarin;
Molecular formula	C 19 H 12 O 6
Brief description	colorless, slightly bitter-tasting crystals
External identifiers / databases
EC number	200-632-9
ECHA InfoCard	100,000,575
PubChem	54676038
DrugBank	DB00266
Wikidata	Q420886
Drug information
ATC code	B01 AA01
Drug class	Anticoagulants
Mechanism of action	Vitamin K antagonist
properties
Molar mass	336.29 g · mol -1
Physical state	firmly
Melting point	287-293 ° C
solubility	soluble in aqueous and organic solutions, benzene and chloroform
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 301-372-411
	P: 260-264-273-280-301 + 310-314
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dicumarol or dicoumarol (formerly known as melitoxin ) is the international non-proprietary name of the chemical compound 3,3'-methylenebis (4-hydroxycoumarin); Dicumarol belongs to the group of 4-hydroxycoumarins and vitamin K antagonists .

Clinical information

Application areas (indications)

It is used for controlled anticoagulation , for example in the treatment or prevention of a tendency to thrombotic diseases. As a rodenticide in the fight against rodents , it causes profuse bleeding and tissue destruction.

Adverse effects (side effects)

Possible side effects of dicumarol are bleeding and hematomas that occur due to its inhibition of blood clotting.

Pharmacological properties

Mechanism of action (pharmacodynamics)

It exerts its anticoagulant effect by inhibiting the enzymatic reduction of Vitamin K . It works just like other coumarin derivatives .

Absorption and distribution in the body (pharmacokinetics)

Dicumarol is taken orally and is ultimately largely absorbed by the intestine. In the bloodstream it binds and changes the proteins of the blood plasma ; eventually it is broken down again in the liver.

History

As a "hemorrhagic agent" (active ingredient that causes bleeding), dicumarol was discovered in 1922 and clinically introduced for the treatment or prevention of thrombosis. It was first isolated from fermented sweet clover ( Melilotus alba ) in 1938 . Dicumarol is responsible for a disease that occurs in North America in cattle that absorb the active ingredient from eaten sweet clover and fermentation in the rumen .

Individual evidence

↑ ^a ^b ^c Entry on dicumarol. In: Römpp Online . Georg Thieme Verlag, accessed on March 6, 2011.
↑ ^a ^b Entry on dicumarin in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
↑ Entry on dicoumarol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Ernst Kern : Seeing - Thinking - Acting of a surgeon in the 20th century. ecomed, Landsberg am Lech 2000, ISBN 3-609-20149-5 , p. 63.

[roempp-1] Entry on dicumarol. In: Römpp Online . Georg Thieme Verlag, accessed on March 6, 2011.

[GESTIS-2] Entry on dicumarin in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[CLP_100.000.575-3] Entry on dicoumarol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[4] Ernst Kern : Seeing - Thinking - Acting of a surgeon in the 20th century. ecomed, Landsberg am Lech 2000, ISBN 3-609-20149-5 , p. 63.