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
SMILES
CC(=O)C[C@@H](C1=CC=CC=C1)C2=C(O)C3=C(OC2=O)C=CC=C3
InChI
InChIKey=PJVWKTKQMONHTI-HNNXBMFYSA-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-/m0/s1
Molecular Formula | C19H16O4 |
Molecular Weight | 308.3279 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/28493597Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/28093289 | https://clinicaltrials.gov/ct2/show/NCT01517399 | https://www.ncbi.nlm.nih.gov/pubmed/27503578 |
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28493597
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/28093289 | https://clinicaltrials.gov/ct2/show/NCT01517399 | https://www.ncbi.nlm.nih.gov/pubmed/27503578 |
Warfarin, (S)- is an oral anticoagulant, S-enantiomer of warfarin, that having a greater pharmacologic potency than the R-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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1930 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28493597 |
0.44 µM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | COUMADIN Approved UseWarfarin sodium tablets are indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, and pulmonary embolism. Warfarin sodium tablets are indicated for the prophylaxis and/or treatment of the thromboembolic complications associated with atrial fibrillation and/or cardiac valve replacement. Warfarin sodium tablets are indicated to reduce the risk of death, recurrent myocardial infarction, and thromboembolic events such as stroke or systemic embolization after myocardial infarction. Launch Date1954 |
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Primary | COUMADIN Approved UseWarfarin sodium tablets are indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, and pulmonary embolism. Warfarin sodium tablets are indicated for the prophylaxis and/or treatment of the thromboembolic complications associated with atrial fibrillation and/or cardiac valve replacement. Warfarin sodium tablets are indicated to reduce the risk of death, recurrent myocardial infarction, and thromboembolic events such as stroke or systemic embolization after myocardial infarction. Launch Date1954 |
|||
Preventing | COUMADIN Approved UseWarfarin sodium tablets are indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, and pulmonary embolism. Warfarin sodium tablets are indicated for the prophylaxis and/or treatment of the thromboembolic complications associated with atrial fibrillation and/or cardiac valve replacement. Warfarin sodium tablets are indicated to reduce the risk of death, recurrent myocardial infarction, and thromboembolic events such as stroke or systemic embolization after myocardial infarction. Launch Date1954 |
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Primary | COUMADIN Approved UseWarfarin sodium tablets are indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, and pulmonary embolism. Warfarin sodium tablets are indicated for the prophylaxis and/or treatment of the thromboembolic complications associated with atrial fibrillation and/or cardiac valve replacement. Warfarin sodium tablets are indicated to reduce the risk of death, recurrent myocardial infarction, and thromboembolic events such as stroke or systemic embolization after myocardial infarction. Launch Date1954 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28493597
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6712738
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
Created
by
admin
on
Edited
Sat Dec 16 08:00:20 GMT 2023
by
admin
on
Sat Dec 16 08:00:20 GMT 2023
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Record UNII |
HP31W7FNP4
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Record Status |
Validated (UNII)
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C263
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
with hepatic microsomal preparations from 33 individuals
revealed that the mean ra tes of formation of metabolites of S-warfarin decreased i n the order
7-0H >> 6-0H = 4-0H = dehycl rowarfarin > 8-0H = 10-0H (Kaminsky ct al. , 1984)
IN-VITRO
MODERATE
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE LESS ACTIVE -> PARENT | |||
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METABOLITE LESS ACTIVE -> PARENT |