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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H16O4
Molecular Weight 308.3287
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

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

SMILES

CC(=O)C[C@@]([H])(c1ccccc1)c2c(c3ccccc3oc2=O)O

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

HIDE SMILES / InChI

Molecular Formula C19H16O4
Molecular Weight 308.3287
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.44 µM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
COUMADIN

Approved Use

Warfarin 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 Date

-4.91443192E11
Primary
COUMADIN

Approved Use

Warfarin 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 Date

-4.91443192E11
Preventing
COUMADIN

Approved Use

Warfarin 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 Date

-4.91443192E11
Primary
COUMADIN

Approved Use

Warfarin 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 Date

-4.91443192E11
PubMed

PubMed

TitleDatePubMed
Population differences in S-warfarin pharmacokinetics among African Americans, Asians and whites: their influence on pharmacogenetic dosing algorithms.
2017 Dec
Patents

Patents

Sample Use Guides

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
Created
by admin
on Sat Jun 26 05:48:59 UTC 2021
Edited
by admin
on Sat Jun 26 05:48:59 UTC 2021
Record UNII
HP31W7FNP4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
WARFARIN, (S)-
Common Name English
(-)-WARFARIN
Common Name English
COUMARIN, 3-(.ALPHA.-ACETONYLBENZYL)-4-HYDROXY-, (S)-(-)-
Systematic Name English
2H-1-BENZOPYRAN-2-ONE, 4-HYDROXY-3-(3-OXO-1-PHENYLBUTYL)-, (S)-
Systematic Name English
S-WARFARIN
Common Name English
4-HYDROXY-3-((1S)-3-OXO-1-PHENYLBUTYL)-2H-1-BENZOPYRAN-2-ONE
Systematic Name English
(S)-WARFARIN
Common Name English
2H-1-BENZOPYRAN-2-ONE, 4-HYDROXY-3-((1S)-3-OXO-1-PHENYLBUTYL)-
Systematic Name English
WARFARIN, L-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C263
Created by admin on Sat Jun 26 05:48:59 UTC 2021 , Edited by admin on Sat Jun 26 05:48:59 UTC 2021
Code System Code Type Description
DRUG BANK
DB14055
Created by admin on Sat Jun 26 05:48:59 UTC 2021 , Edited by admin on Sat Jun 26 05:48:59 UTC 2021
PRIMARY
NCI_THESAURUS
C148031
Created by admin on Sat Jun 26 05:48:59 UTC 2021 , Edited by admin on Sat Jun 26 05:48:59 UTC 2021
PRIMARY NCIT
ECHA (EC/EINECS)
226-907-3
Created by admin on Sat Jun 26 05:48:59 UTC 2021 , Edited by admin on Sat Jun 26 05:48:59 UTC 2021
PRIMARY
CAS
5543-57-7
Created by admin on Sat Jun 26 05:48:59 UTC 2021 , Edited by admin on Sat Jun 26 05:48:59 UTC 2021
PRIMARY
PUBCHEM
54688261
Created by admin on Sat Jun 26 05:48:59 UTC 2021 , Edited by admin on Sat Jun 26 05:48:59 UTC 2021
PRIMARY
FDA UNII
HP31W7FNP4
Created by admin on Sat Jun 26 05:48:59 UTC 2021 , Edited by admin on Sat Jun 26 05:48:59 UTC 2021
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
METABOLITE -> PARENT
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
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE LESS ACTIVE -> PARENT
METABOLITE LESS ACTIVE -> PARENT