dicoumarol

Small moleculeapproved

Approved

Jun 1, 1944

Dicumarol is an coumarin-like compound found in sweet clover. It is used as oral anticoagulant and acts by inhibiting the hepatic synthesis of vitamin K-dependent coagulation factors (prothrombin and factors VII, IX, and X). It results in decresed prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots. Dicumarol is also used in biochemical experiments as an inhibitor of reductases. — NCATS

Clinical trial activity

0 trials · 0 clinical orgs · 2 marketing orgs

Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Timeline

1940s

  1. Jun 1, 1944

    Earliest FDA Approval

  2. Jul 31, 1944

    AbbVie — NDA Secondary Org

1970s

  1. Apr 9, 1976

    Eli Lilly — First NDA Organization

  2. Apr 9, 1976

    Eli Lilly — NDA Organization

Indications

Mechanism of action

Approval history

  • approvedJun 1, 1944

Chemistry & pharmacology

Loading structure…

SMILES

OC1=C(CC2=C(O)C3=C(OC2=O)C=CC=C3)C(=O)OC4=C1C=CC=C4
Mol. weight
336.295 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Achiral Molecule
Inorganic
No
Polymer
No
Delivery
Oral
Availability
Discontinued

Oral

Yes

Parenteral

No

Topical

No

Sources

Also known as

  • 3,3'-methylen-bis(4-hydroxy-cumarin)
  • 3,3'-methylen-bis(4-hydroxy-cumarin)
  • 3,3'-methylenebis(4-hydroxy-1,2-benzopyrone)
  • 3,3'-methylenebis(4-hydroxy-1,2-benzopyrone)
  • 3,3'-methylenebis(4-hydroxy-2h-1-benzopyran-2-one)
  • 3,3'-methylenebis(4-hydroxy-2h-1-benzopyran-2-one)
  • 3,3'-methylenebis(4-hydroxycoumarin)
  • 3,3'-methylenebis(4-hydroxycoumarin)
  • 3,3'-methylene-bis(4-hydroxycoumarine)
  • 3,3'-methylene-bis(4-hydroxycoumarine)
  • bis-3,3'-(4-hydroxycoumarinyl)methane
  • bis-3,3'-(4-hydroxycoumarinyl)methane
  • bis(4-hydroxycoumarin-3-yl)methane
  • bis(4-hydroxycoumarin-3-yl)methane
  • bishydroxycoumarin
  • bishydroxycoumarin
  • bishydroxycoumarin
  • bis-hydroxycoumarin
  • bis-hydroxycoumarin
  • di-(4-hydroxy-3-coumarinyl)methane
  • di-(4-hydroxy-3-coumarinyl)methane
  • dicoumal
  • dicoumarin
  • dicoumarol
  • dicoumarol
  • dicoumarol
  • dicoumarol
  • dicoumarol
  • dicoumarol
  • dicoumarol
  • dicoumarol
  • dicoumarolum
  • dicoumarolum
  • dicuman
  • dicumarine
  • dicumarol
  • dicumarol
  • dicumarol
  • dicumarol
  • dicumarol
  • dicumarol
  • dicumarol
  • trombosan
  • trombosan

Organizations

Marketing (2)

OrganizationOrg typeRelationshipDate
AbbVieFor profitNDA2Jul 31, 1944
Eli LillyFor profitNDAApr 9, 1976