Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C19H15O4.Na |
| Molecular Weight | 330.3098 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CC(=O)CC(C1=CC=CC=C1)C2=C([O-])C3=C(OC2=O)C=CC=C3
InChI
InChIKey=KYITYFHKDODNCQ-UHFFFAOYSA-M
InChI=1S/C19H16O4.Na/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;/q;+1/p-1
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C19H15O4 |
| Molecular Weight | 307.32 |
| Charge | -1 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
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 Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 24.7 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| 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 |
|||
| 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 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2186 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19552747 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
WARFARIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
52278 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19552747 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
WARFARIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
7 day |
single, oral |
WARFARIN plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
32.4 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19552747 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
WARFARIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1% |
single, oral |
WARFARIN plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
125 mg single, oral Overdose |
unhealthy, 43 |
Disc. AE: Vomiting, Loss of consciousness... AEs leading to discontinuation/dose reduction: Vomiting Sources: Loss of consciousness |
150 mg single, oral Overdose |
unhealthy, 44 |
Disc. AE: Drowsiness... AEs leading to discontinuation/dose reduction: Drowsiness Sources: |
540 mg single, oral Overdose |
healthy, 59 |
|
5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy, 64 |
Disc. AE: Hemoptysis, Hematuria... AEs leading to discontinuation/dose reduction: Hemoptysis Sources: Hematuria Dyspnea Cough |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Bleeding... AEs leading to discontinuation/dose reduction: Bleeding (grade 5) Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Loss of consciousness | Disc. AE | 125 mg single, oral Overdose |
unhealthy, 43 |
| Vomiting | Disc. AE | 125 mg single, oral Overdose |
unhealthy, 43 |
| Drowsiness | Disc. AE | 150 mg single, oral Overdose |
unhealthy, 44 |
| Cough | Disc. AE | 5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy, 64 |
| Dyspnea | Disc. AE | 5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy, 64 |
| Hematuria | Disc. AE | 5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy, 64 |
| Hemoptysis | Disc. AE | 5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy, 64 |
| Bleeding | grade 5 Disc. AE |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes [Ki 8 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | ||||
| yes | ||||
| yes | ||||
| yes | likely (co-administration study) Comment: Inhibitors of CYP2C9, 1A2, and/or 3A4 have the potential to increase the effect (increase INR) of warfarin by increasing the exposure of warfarin; Inducers of CYP2C9, 1A2, and/or 3A4 have the potential to decrease the effect (decrease INR) of warfarin by decreasing the exposure of warfarin Page: 14.0 |
|||
| yes | likely (co-administration study) Comment: Inhibitors of CYP2C9, 1A2, and/or 3A4 have the potential to increase the effect (increase INR) of warfarin by increasing the exposure of warfarin; Inducers of CYP2C9, 1A2, and/or 3A4 have the potential to decrease the effect (decrease INR) of warfarin by decreasing the exposure of warfarin Page: 14.0 |
|||
| yes | yes (pharmacogenomic study) Comment: If the patient’s CYP2C9 and/or VKORC1 genotype are known, consider these ranges in choosing the initial dose. Patients with CYP2C9 *1/*3, *2/*2, *2/*3, and *3/*3 may require more prolonged time (>2 to 4 weeks) to achieve maximum INR effect for a given dosage regimen than patients without these CYP variants; Inhibitors of CYP2C9, 1A2, and/or 3A4 have the potential to increase the effect (increase INR) of warfarin by increasing the exposure of warfarin; Inducers of CYP2C9, 1A2, and/or 3A4 have the potential to decrease the effect (decrease INR) of warfarin by decreasing the exposure of warfarin Page: 14.0 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Potentiation of anticoagulant effect of warfarin caused by enantioselective metabolic inhibition by the uricosuric agent benzbromarone. | 1999 Dec |
|
| Increased risk of intracranial hemorrhage when aspirin is combined with warfarin: A meta-analysis and hypothesis. | 1999 Jul-Aug |
|
| Bleeding during warfarin and aspirin therapy in patients with atrial fibrillation: the AFASAK 2 study. Atrial Fibrillation Aspirin and Anticoagulation. | 1999 Jun 28 |
|
| Analysis of risk factors involved in oral-anticoagulant-related intracranial haemorrhages. | 2000 Aug |
|
| Warfarin-induced artery calcification is accelerated by growth and vitamin D. | 2000 Feb |
|
| Anticoagulant induced submucosal hemorrhage mimicking a renal pelvic tumor. | 2000 Jan |
|
| Intraspinal hemorrhage complicating oral anticoagulant therapy: an unusual case of cervical hematomyelia and a review of the literature. | 2000 Jan 24 |
|
| Oral anticoagulants. Pharmacologic issues for use in the elderly. | 2001 Feb |
|
| Anticoagulation and cataract surgery: a review of the current literature. | 2001 Feb |
|
| [Incidence of tumors after treatment with oral anticoagulants]. | 2001 Feb |
|
| Subtherapeutic INR values associated with a switch to generic warfarin. | 2001 Feb |
|
| Current trends in the management of deep venous thrombosis and postthrombotic syndrome. | 2001 Feb |
|
| Kidney retransplants after initial graft loss to vascular thrombosis. | 2001 Feb |
|
| Anticoagulant pharmacodynamics of tinzaparin following 175 iu/kg subcutaneous administration to healthy volunteers. | 2001 Feb 15 |
|
| What is the best emergency treatment for children who ingest warfarin rodenticide? | 2001 Feb 5 |
|
| Inhibition of human cytochrome P450 isoforms by nonnucleoside reverse transcriptase inhibitors. | 2001 Jan |
|
| Hypertension due to renal artery occlusion in a patient with antiphospholipid syndrome. | 2001 Jan |
|
| Antithrombotic therapy in patients with mechanical and biological prosthetic heart valves. | 2001 Jan |
|
| Anticoagulation and heart failure. | 2001 Jan |
|
| Is optimal antithrombotic therapy after myocardial infarction well defined? | 2001 Jan |
|
| Need for increased dose of warfarin in HIV patients taking nevirapine. | 2001 Jan 26 |
|
| Primary antiphospholipid syndrome masquerading as diabetic retinopathy. | 2001 Jan-Feb |
|
| Prevention, diagnosis, and treatment of venous thromboembolic complications of gynecologic surgery. | 2001 Mar |
|
| The association of vitamin K status with warfarin sensitivity at the onset of treatment. | 2001 Mar |
|
| A case report of warfarin resistance due to azathioprine and review of the literature. | 2001 Mar |
|
| Antiphospholipid antibody syndrome and renal disease. | 2001 Mar |
|
| When should an effective treatment be used? Derivation of the threshold number needed to treat and the minimum event rate for treatment. | 2001 Mar |
|
| Mild head injury, anticoagulants, and risk of intracranial injury. | 2001 Mar 10 |
|
| Dalteparin vs warfarin in hip arthroplasty patients. | 2001 Mar 12 |
|
| Warfarin therapy for an octogenarian who has atrial fibrillation. | 2001 Mar 20 |
|
| What is the optimal medical management of ischemic heart failure? | 2001 Mar-Apr |
Patents
Sample Use Guides
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
Curator's Comment: One strain (TAS) is susceptible and two strains (HW and HS) resistant to the anticoagulant and lethal effects of warfarin.
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
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admin
on
Edited
Mon Mar 31 17:46:39 GMT 2025
by
admin
on
Mon Mar 31 17:46:39 GMT 2025
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| Record UNII |
6153CWM0CL
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C45597
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EPA PESTICIDE CODE |
86003
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NCI_THESAURUS |
C263
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100000092049
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129-06-6
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204-929-4
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SUB05128MIG
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warfarin-sodium
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16204922
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C1658
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10034
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WARFARIN SODIUM
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PRIMARY | Description: A white, amorphous or crystalline powder; odourless. Solubility: Soluble in less than 1 part of water and in ethanol (~750 g/l) TS; slightly soluble in ether R. Category: Anticoagulant. Storage: Warfarin sodium should be kept in a well-closed container, protected from light. Labelling: The designation on the container of Warfarin sodium should state whether the substance is in the amorphous or the crystalline, clathrate form. Additional information: Warfarin sodium is discoloured by light. Even in the absence of light, it is gradually degraded on exposureto a humid atmosphere, the decomposition being faster at higher temperatures.Definition: Warfarin sodium contains not less than 98.0% and not more than 102.0% of C19H15NaO4, calculated with reference to the anhydrous and 2-propanol-free substance. | ||
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CHEMBL1464
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m11506
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DTXSID7035010
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DBSALT000278
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114194
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PRIMARY | RxNorm |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
SOLVATE->ANHYDROUS |
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|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
|
||
|
|
PARENT -> SALT/SOLVATE | |||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (UV)
EP
|
||
|
SOLVATE->ANHYDROUS |
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
correction factors: for the calculation of content, multiply the peak areas of the following impurities by the corresponding correction factor: impurity C = 0.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
correction factors: for the calculation of content, multiply the peak areas of the following impurity by the corresponding correction factor: impurity B = 0.5
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |