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Details

Stereochemistry ACHIRAL
Molecular Formula C19H12O6
Molecular Weight 336.295
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DICUMAROL

SMILES

OC1=C(CC2=C(O)C3=CC=CC=C3OC2=O)C(=O)OC4=CC=CC=C14

InChI

InChIKey=DOBMPNYZJYQDGZ-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C19H12O6
Molecular Weight 336.295
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.0 µM [IC50]
10.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
DICUMAROL

Cmax

ValueDoseCo-administeredAnalytePopulation
20 μg/mL
6 mg/kg single, intravenous
DICUMAROL plasma
Rattus norvegicus

AUC

ValueDoseCo-administeredAnalytePopulation
521 μg × h/mL
6 mg/kg single, intravenous
DICUMAROL plasma
Rattus norvegicus

T1/2

ValueDoseCo-administeredAnalytePopulation
12.84 h
6 mg/kg single, intravenous
DICUMAROL plasma
Rattus norvegicus

Funbound

ValueDoseCo-administeredAnalytePopulation
0.03%
6 mg/kg single, intravenous
DICUMAROL plasma
Rattus norvegicus

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Oral
In Vitro Use Guide
Dicoumarol inhibits rat liver microsomal vitamin K epoxide reductase with IC50=2 uM and cytosolic DT-diaphorase with IC50=0.05 uM.
Substance Class Chemical
Record UNII
7QID3E7BG7
Record Status Validated (UNII)
Record Version