Details
| Stereochemistry | RACEMIC |
| Molecular Formula | 2C19H15O4.C3H8O.2Na |
| Molecular Weight | 720.7146 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[Na+].CC(C)O.CC(=O)CC(C1=CC=CC=C1)C2=C([O-])C3=C(OC2=O)C=CC=C3.CC(=O)CC(C4=CC=CC=C4)C5=C([O-])C6=C(OC5=O)C=CC=C6
InChI
InChIKey=VLYIGFRRLKDPQS-UHFFFAOYSA-L
InChI=1S/2C19H16O4.C3H8O.2Na/c2*1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22;1-3(2)4;;/h2*2-10,15,21H,11H2,1H3;3-4H,1-2H3;;/q;;;2*+1/p-2
| 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 | ( + / - ) |
| Molecular Formula | C3H8O |
| Molecular Weight | 60.095 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
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 |
|---|---|---|
| Chondrodysplasia punctata and maternal warfarin use during pregnancy. | 1975 Mar |
|
| Heparin-induced thrombocytopenia: a ten-year retrospective. | 1999 |
|
| [Treatment of cardiac insufficiency: does treatment depend on whether its cause is ischemic or idiopathic?]. | 1999 Jun |
|
| Multicentric warfarin-induced skin necrosis complicating heparin-induced thrombocytopenia. | 1999 Sep |
|
| Anticoagulant induced submucosal hemorrhage mimicking a renal pelvic tumor. | 2000 Jan |
|
| Genetic modulation of oral anticoagulation with warfarin. | 2000 Nov |
|
| Warfarin-associated hemorrhage and cerebral amyloid angiopathy: a genetic and pathologic study. | 2000 Oct 10 |
|
| [Marked creatine-phosphokinase elevation in myopathy after treatment with bezafibrate]. | 2000 Sep |
|
| Central retinal vein occlusion associated with primary pulmonary hypertension. | 2001 |
|
| Abdominal wall hematoma as a complication of warfarinization. | 2001 Apr |
|
| Spontaneous subcapsular renal hematoma secondary to anticoagulant therapy. | 2001 Apr |
|
| Perioperative management and reversal of antithrombotic therapy. | 2001 Feb |
|
| Thrombolysis and antithrombotic therapy for coronary artery disease. | 2001 Feb |
|
| Anticoagulation and cataract surgery: a review of the current literature. | 2001 Feb |
|
| Implications of cytochrome P450 2C9 polymorphism on warfarin metabolism and dosing. | 2001 Feb |
|
| Sevelamer hydrochloride (Renagel), a nonabsorbed phosphate-binding polymer, does not interfere with digoxin or warfarin pharmacokinetics. | 2001 Feb |
|
| Asymptomatic atrial fibrillation: problems of management. | 2001 Feb |
|
| How safely and for how long can warfarin therapy be withheld in prosthetic heart valve patients hospitalized with a major hemorrhage? | 2001 Feb |
|
| Kidney retransplants after initial graft loss to vascular thrombosis. | 2001 Feb |
|
| Systematic review of long term anticoagulation or antiplatelet treatment in patients with non-rheumatic atrial fibrillation. | 2001 Feb 10 |
|
| Regarding postoperative stroke after warfarin for cutaneous surgery. | 2001 Jan |
|
| Catastrophic antiphospholipid antibody syndrome. | 2001 Jan |
|
| Inhibition of human cytochrome P450 isoforms by nonnucleoside reverse transcriptase inhibitors. | 2001 Jan |
|
| Regarding clinical practice guidelines on the use of warfarin. | 2001 Jan |
|
| The sin of omission: a systematic review of antithrombotic therapy to prevent stroke in atrial fibrillation. | 2001 Jan |
|
| Hypertension due to renal artery occlusion in a patient with antiphospholipid syndrome. | 2001 Jan |
|
| Cardiac and great vessel thrombosis in Behçet's disease. | 2001 Jan |
|
| Antithrombotic therapy for prosthetic valves: routine treatment and special considerations. | 2001 Jan |
|
| Is optimal antithrombotic therapy after myocardial infarction well defined? | 2001 Jan |
|
| Molecular dynamics study of the IIA binding site in human serum albumin: influence of the protonation state of Lys195 and Lys199. | 2001 Jan 18 |
|
| Clinical problem-solving. High time for action. | 2001 Jan 4 |
|
| Acute spontaneous haematoma of the rectum. | 2001 Jan-Feb |
|
| Primary antiphospholipid syndrome masquerading as diabetic retinopathy. | 2001 Jan-Feb |
|
| Sneddon's syndrome: a case report. | 2001 Mar |
|
| Perception of teratogenic risk of common medicines. | 2001 Mar |
|
| Increase in international normalized ratio associated with smoking cessation. | 2001 Mar |
|
| The association of vitamin K status with warfarin sensitivity at the onset of treatment. | 2001 Mar |
|
| Evaluation of very low-dose subcutaneous vitamin K during postoperative warfarin therapy. | 2001 Mar |
|
| Treatment of the patient with deep vein thrombosis. | 2001 Mar |
|
| Aspirin does not influence the effect of angiotensin-converting enzyme inhibition on left ventricular ejection fraction 3 months after acute myocardial infarction. | 2001 Mar |
|
| Hemoptysis in patients with renal insufficiency : the role of flexible bronchoscopy. | 2001 Mar |
|
| Efficacy and safety of intravenous phytonadione (vitamin K1) in patients on long-term oral anticoagulant therapy. | 2001 Mar |
|
| Management of thrombosis in women with antiphospholipid syndrome. | 2001 Mar |
|
| Adverse reactions to fluoroquinolones. an overview on mechanistic aspects. | 2001 Mar |
|
| Dalteparin vs warfarin in hip arthroplasty patients. | 2001 Mar 12 |
|
| 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
by
admin
on
Edited
Mon Mar 31 17:34:23 GMT 2025
by
admin
on
Mon Mar 31 17:34:23 GMT 2025
|
| Record UNII |
4V2UBU7H8W
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
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Common Name | English | ||
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Preferred Name | English | ||
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Common Name | English |
| Code System | Code | Type | Description | ||
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4V2UBU7H8W
Created by
admin on Mon Mar 31 17:34:23 GMT 2025 , Edited by admin on Mon Mar 31 17:34:23 GMT 2025
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145996738
Created by
admin on Mon Mar 31 17:34:23 GMT 2025 , Edited by admin on Mon Mar 31 17:34:23 GMT 2025
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PARENT -> SALT/SOLVATE |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |
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