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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H16O4
Molecular Weight 308.3279
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of WARFARIN, (R)-

SMILES

CC(=O)C[C@H](C1=CC=CC=C1)C2=C(O)C3=C(OC2=O)C=CC=C3

InChI

InChIKey=PJVWKTKQMONHTI-OAHLLOKOSA-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/t15-/m1/s1

HIDE SMILES / InChI

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

Description

Warfarin, (R)- is R-enantiomer of warfarin, an oral anticoagulant, with relatively low potency compared to S-enantiomer. Clinically available warfarin is a racemic mixture of (R)- and (S)-warfarin, and the (S)-enantiomer has 3 to 5 times greater anticoagulation potency than its optical congener. Both enantiomers are eliminated extensively via hepatic metabolism with low clearance relative to hepatic blood flow. The scientific debate on the contribution of the R- Warfarin -to-S- Warfarin effect is a long and conflictual story. It has shown that the pharmacodynamic response to (R/S)-Warfarin 25 mg (a mixture of equal amounts of S-Warfarin and R- Warfarin) was nearly twice that of S-Warfarin 12.5 mg given alone, thus indicating the substantial contribution of R-Warfarin to the (R/S)-Warfarin effect. (R/S)-Warfarin 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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.36 µM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
COUMADIN
Preventing
COUMADIN
Primary
COUMADIN
Preventing
COUMADIN

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Prevention of Thromboembolism in Atrial Fibrillation Initial dose: 2 to 5 mg (R/S-Warfarin) orally once a day Maintenance dose: 2 to 10 mg (R/S-Warfarin) orally once a day Usual Adult Dose for Myocardial Infarction Initial dose: 2 to 5 mg (R/S-Warfarin) orally once a day Maintenance dose: 2 to 10 mg (R/S-Warfarin) orally once a day Usual Adult Dose for Deep Vein Thrombosis - Prophylaxis Initial dose: 2 to 5 mg (R/S-Warfarin) orally once a day Maintenance dose: 2 to 10 mg (R/S-Warfarin) 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
09CC5J5C8A
Record Status Validated (UNII)
Record Version