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Dicoumarol information


Dicoumarol
Clinical data
MedlinePlusa605015
ATC code
  • B01AA01 (WHO)
Legal status
Legal status
  • US: Withdrawn from market
Pharmacokinetic data
Protein bindingplasmatic proteins
Metabolismhepatic
Excretionfaeces, urine
Identifiers
IUPAC name
  • 3,3'-Methylenebis(4-hydroxy-2H-chromen-2-one)
CAS Number
  • 66-76-2 checkY
PubChem CID
  • 653
IUPHAR/BPS
  • 6808
DrugBank
  • DB00266 ☒N
ChemSpider
  • 10183330 checkY
UNII
  • 7QID3E7BG7
KEGG
  • D03798 checkY
ChEBI
  • CHEBI:4513 checkY
ChEMBL
  • ChEMBL1466 checkY
NIAID ChemDB
  • 016070
CompTox Dashboard (EPA)
  • DTXSID8021729 Edit this at Wikidata
ECHA InfoCard100.000.575 Edit this at Wikidata
Chemical and physical data
FormulaC19H12O6
Molar mass336.299 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 checkY
  • Key:DOBMPNYZJYQDGZ-UHFFFAOYSA-N checkY
 ☒NcheckY (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 Dicoumarol itself, for a short time, was employed as a medicinal anticoagulant drug, but since the mid-1950s has been replaced by its simpler derivative warfarin, and other 4-hydroxycoumarin drugs.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.

  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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Dicoumarol

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Dicoumarol (INN) or dicumarol (USAN) is a naturally occurring anticoagulant drug that depletes stores of vitamin K (similar to warfarin, a drug that dicoumarol...

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Melilotus

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Fusarium, and Mucor) can convert coumarin into dicoumarol, a toxic anticoagulant. Consequently, dicoumarol may be found in decaying sweet-clover, and was...

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Coumarin derivatives

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formaldehyde) into the actual anticoagulant dicoumarol, a fermentation product and mycotoxin. Dicoumarol was responsible for the bleeding disease known...

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Melilotus officinalis

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native plant species. Sweet clover contains coumarin that converts to dicoumarol, which is a powerful anticoagulant toxin, when the plant becomes moldy...

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Warfarin

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3'-methylenebis-(4-hydroxycoumarin), which they later named dicoumarol. They confirmed their results by synthesizing dicoumarol and proving in 1940 that it was identical...

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Karl Paul Link

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synthesised and tested it; it turned out to be dicoumarol (3,3'-methylenebis-(4 hydroxycoumarin)). Dicoumarol was subjected to clinical trials in Wisconsin...

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Uncoupler

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1β,3α-dihydroxyeudesm-7,8-ene) (produced by Verbesina) CZ5 Desaspidin Dicoumarol Dinitro-ortho-cresol (DNOC) Ellipticine Endosidin 9 (ES9) Flufenamic acid...

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Coumarin

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synthesis of a number of synthetic anticoagulant pharmaceuticals similar to dicoumarol. 4-hydroxycoumarins are a type of vitamin K antagonist. They block the...

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Vitamin K antagonist

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4-hydroxycoumarins. Warfarin (Coumadin) Coumatetralyl Phenprocoumon Acenocoumarol Dicoumarol Tioclomarol Brodifacoum Another group of VKAs are 1,3-indandione derivatives...

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ATC code B01

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codes not present in this list, which follows the WHO version. B01AA01 Dicoumarol B01AA02 Phenindione B01AA03 Warfarin B01AA04 Phenprocoumon B01AA07 Acenocoumarol...

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Brodifacoum

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anticoagulant, with a similar mode of action to its historical predecessors dicoumarol and warfarin. However, due to very high potency and long duration of action...

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Benzopyrone

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for various 4-hydroxybenzopyrone-based molecules which occur naturally dicoumarol and are made synthetically warfarin and function as anticoagulants. full...

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Melilotus albus

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affected by salinity. It has been used in herbal medicine. It includes dicoumarol, which is an anticoagulant. It also has a high sugar content. White sweetclover...

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List of drugs by year of discovery

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Methylphenobarbital 1935 1935 1935 1955 1935 Dapsone 1935 1935 1935 1955 1940 Dicoumarol (warfarin) 1940, extracted from Melilotus 1940 1940 1960 1946 Isosorbide...

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List of nominees for the Nobel Prize in Physiology or Medicine

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"Neurophysiology, in particular the physiological basis of electroencephalography" "Dicoumarol and related compounds" “for their discovery of the ability of poliomyelitis...

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List of nominees for the Nobel Prize in Chemistry

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especially stilboestrol (diethylstilbestrol, DES) and their effects." "Dicoumarol and related compounds" “for their discoveries in the chemistry of the...

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Discovery and development of direct Xa inhibitors

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substance causing the internal bleeding. It took them 6 years to discover dicoumarol, the causing agent. They patented the right for the substance and in 1945...

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