dicumarol
Also known as bishydroxycoumarin, Melitoxin®, Dicoumarol, bis-hydroxycoumarin, bis(4-hydroxycoumarin-3-yl)methane, bis-3,3'-(4-hydroxycoumarinyl)methane, 3,3'-methylenebis(4-hydroxy-2H-1-benzopyran-2-one), 3,3'-methylenebis(4-hydroxy-1,2-benzopyrone)
Dicoumarol (INN) or dicumarol (USAN) is a naturally occurring anticoagulant drug that depletes stores of vitamin K (similar to warfarin, a drug that dicoumarol inspired). It is also used in biochemical experiments as an inhibitor of reductases.
Chemical data
- Formula
- C19H12O6
- Molecular weight
- 336.3 g/mol
- IUPAC name
- 4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)methyl]chromen-2-one
- SMILES
- C1=CC=C2C(=C1)C(=C(C(=O)O2)CC3=C(C4=CC=CC=C4OC3=O)O)O
- InChIKey
- DOBMPNYZJYQDGZ-UHFFFAOYSA-N
- XLogP
- 2.6
- Polar surface area
- 93.1 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
2,528 papersArticle
8 sectionsContents
- Uses
- Mechanism of action
- Poisoning
- History
- See also
- References
- Further reading
- External links
Dicoumarol (INN) or dicumarol (USAN) is a naturally occurring anticoagulant drug that depletes stores of vitamin K (similar to warfarin, a drug that dicoumarol inspired). It is also used in biochemical experiments as an inhibitor of reductases.
Dicoumarol is a natural chemical substance of combined plant and fungal origin. It is a derivative of coumarin, a bitter-tasting but sweet-smelling substance made by plants that does not itself affect coagulation, but which is (classically) transformed in mouldy feeds or silages by a number of species of fungi, into active dicoumarol. Dicoumarol does affect coagulation, and was discovered in mouldy wet sweet-clover hay, as the cause of a naturally occurring bleeding disease in cattle. See warfarin for a more detailed discovery history.