Dicoumarol

Pharmaceutical compound

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Legal status	US: Withdrawn from market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)
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 Y Key:DOBMPNYZJYQDGZ-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Dicoumarol (

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 Dicoumarol itself, for a short time, was employed as a medicinal anticoagulant drug, but since the mid-1950s has been replaced by its simpler derivative warfarin, and other 4-hydroxycoumarin drugs.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

Dicoumarol was used, along with heparin, for the treatment of deep venous thrombosis. Unlike heparin, this class of drugs may be used for months or years.

Like all 4-hydroxycoumarin drugs it is a

• Ethyl biscoumacetate

Further reading

This article includes a list of general references, but it lacks sufficient corresponding inline citations. Please help to improve this article by introducing more precise citations. (September 2011) (Learn how and when to remove this message)

• Cullen JJ, Hinkhouse MM, Grady M, Gaut AW, Liu J, Zhang YP, et al. (September 2003). "Dicumarol inhibition of NADPH:quinone oxidoreductase induces growth inhibition of pancreatic cancer via a superoxide-mediated mechanism". Cancer Research. 63 (17): 5513–5520.
  PMID 14500388
  .
• Mironov AA, Colanzi A, Polishchuk RS, Beznoussenko GV, Mironov AA, Fusella A, et al. (July 2004). "Dicumarol, an inhibitor of ADP-ribosylation of CtBP3/BARS, fragments golgi non-compact tubular zones and inhibits intra-golgi transport". European Journal of Cell Biology. 83 (6): 263–279.
  PMID 15511084
  .
• Abdelmohsen K, Stuhlmann D, Daubrawa F, Klotz LO (February 2005). "Dicumarol is a potent reversible inhibitor of gap junctional intercellular communication". Archives of Biochemistry and Biophysics. 434 (2): 241–247.
  PMID 15639223
  .
• Thanos CG, Liu Z, Reineke J, Edwards E, Mathiowitz E (July 2003). "Improving relative bioavailability of dicumarol by reducing particle size and adding the adhesive poly(fumaric-co-sebacic) anhydride". Pharmaceutical Research. 20 (7): 1093–1100.
  S2CID 448086
  .]

External links

• Diseases Database (DDB): 30166