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Details

Stereochemistry RACEMIC
Molecular Formula C19H16O4
Molecular Weight 308.3279
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of WARFARIN

SMILES

CC(=O)CC(C1=CC=CC=C1)C2=C(O)C3=C(OC2=O)C=CC=C3

InChI

InChIKey=PJVWKTKQMONHTI-UHFFFAOYSA-N
InChI=1S/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3

HIDE SMILES / InChI

Molecular Formula C19H16O4
Molecular Weight 308.3279
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Warfarin is an anticoagulant drug normally used to prevent blood clot formation as well as migration. Warfarin is marketed under the brand name Coumadin among others. Coumadin (crystalline warfarin sodium) is an anticoagulant which acts by inhibiting vitamin K-dependent coagulation factors. Chemically, it is 3-(α-acetonylbenzyl)-4-hydroxycoumarin and is a racemic mixture of the R- and S-enantiomers. Coumadin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, and pulmonary embolism. It is also indicated for the prophylaxis and/or treatment of the thromboembolic complications associated with atrial fibrillation and/or cardiac valve replacement. Warfarin is thought to interfere with clotting factor synthesis by inhibition of the C1 subunit of the vitamin K epoxide reductase (VKORC1) enzyme complex, thereby reducing the regeneration of vitamin K1 epoxide. The degree of depression is dependent upon the dosage administered and, in part, by the patient’s VKORC1 genotype. Therapeutic doses of warfarin decrease the total amount of the active form of each vitamin K dependent clotting factor made by the liver by approximately 30% to 50%.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
24.7 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
COUMADIN
Preventing
COUMADIN
Preventing
COUMADIN

Cmax

ValueDoseCo-administeredAnalytePopulation
2186 ng/mL
25 mg single, oral
WARFARIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
52278 ng × h/mL
25 mg single, oral
WARFARIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
32.4 h
25 mg single, oral
WARFARIN plasma
Homo sapiens
7 day
single, oral
WARFARIN unknown
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
single, oral
WARFARIN unknown
Homo sapiens

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Prevention of Thromboembolism in Atrial Fibrillation Initial dose: 2 to 5 mg orally once a day Maintenance dose: 2 to 10 mg orally once a day Usual Adult Dose for Myocardial Infarction Initial dose: 2 to 5 mg orally once a day Maintenance dose: 2 to 10 mg orally once a day Usual Adult Dose for Deep Vein Thrombosis - Prophylaxis Initial dose: 2 to 5 mg orally once a day Maintenance dose: 2 to 10 mg orally once a day
Route of Administration: Oral
In Vitro Use Guide
Vitamin K-reductase activity was inhibited by approximately 13 and 8% respectively when microsomal preparations from TAS and HW animals were incubated with 50 uM vitamin K1 and 10 uM warfarin.
Substance Class Chemical
Record UNII
5Q7ZVV76EI
Record Status Validated (UNII)
Record Version