Dicoumarol

Dicoumarol
Clinical data
MedlinePlus	a605015
ATC code	B01AA01 (WHO) ;
Legal status
Legal status	US: Withdrawn from market;
Pharmacokinetic data
Protein binding	plasmatic proteins
Metabolism	hepatic
Excretion	faeces, urine
Identifiers
	IUPAC name 3,3'-Methylenebis(4-hydroxy-2H-chromen-2-one);
CAS Number	66-76-2 ;
PubChem CID	653;
IUPHAR/BPS	6808;
DrugBank	DB00266 ;
ChemSpider	10183330 ;
UNII	7QID3E7BG7;
KEGG	D03798 ;
ChEBI	CHEBI:4513 ;
ChEMBL	ChEMBL1466 ;
NIAID ChemDB	016070;
CompTox Dashboard (EPA)	DTXSID8021729 ;
ECHA InfoCard	100.000.575
Chemical and physical data
Formula	C19H12O6
Molar mass	336.299 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1Oc2ccccc2C(O)=C1CC3=C(O)c4ccccc4OC3=O;
	InChI InChI=1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2 ; Key:DOBMPNYZJYQDGZ-UHFFFAOYSA-N ;
	(what is this?) (verify)

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.^[1] See warfarin for a more detailed discovery history.

Identified in 1940, dicoumarol became the prototype of the 4-hydroxycoumarin anticoagulant drug class. Dicoumarol itself, for a short time, was employed as a medicinal anticoagulant drug, but since the mid-1950s has been replaced by its simpler derivative warfarin, and other 4-hydroxycoumarin drugs.

It is given orally, and it acts within two days.

^ Kresge N, Simoni RD, Hill RL (February 2005). "Hemorrhagic sweet clover disease, dicumarol, and warfarin: the work of Karl Paul Link". Journal of Biological Chemistry. 280 (8): e6–e7. doi:10.1016/S0021-9258(19)62862-0.

[1] Kresge N, Simoni RD, Hill RL (February 2005). "Hemorrhagic sweet clover disease, dicumarol, and warfarin: the work of Karl Paul Link". Journal of Biological Chemistry. 280 (8): e6–e7. doi:10.1016/S0021-9258(19)62862-0.

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