warfarin
Trade name: coumadin
Approved
Jun 8, 1954
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%. — NCATS
Clinical trial activity
393 trials · 346 clinical orgs · 18 marketing orgs
Earliest trial started Jul 1, 1985 (NCT00000517)
Timeline
1950s
- Jun 8, 1954
Bristol-Myers — Earliest FDA Approval
- Jun 8, 1954
Bristol-Myers Squibb — NDA Secondary Org
- Jun 8, 1954
Bristol-Myers — NDA Organization
1970s
- Aug 11, 1972
Abbott — NDA Secondary Org
1980s
- Jan 1, 1985
Earliest Phase 3 Sponsor(trial)
1990s
- Mar 26, 1997
Barr Laboratories — Marketing Organization
- Sep 30, 1997
Chartwell Pharmaceuticals — Marketing Organization
- Sep 30, 1997
Fosun — Marketing Organization
- Jan 1, 1998
Earliest Phase 1 Sponsor(trial)
- Jul 15, 1999
Taro Pharmaceuticals — Marketing Organization
2000s
- Jan 1, 2000
Earliest Phase 2 Sponsor(trial)
- Oct 2, 2003
Upsher-Smith Laboratories — Marketing Organization
- Sep 27, 2004
Aurobindo Pharma — Marketing Organization
- Sep 27, 2004
Mylan — Marketing Organization
- May 30, 2006
Zydus Discovery DMCC — Marketing Organization
- Jul 5, 2006
Pliva — Marketing Organization
2010s
- May 25, 2011
Invagen Pharms — Marketing Organization
- Mar 4, 2013
Amneal Pharmaceuticals — Marketing Organization
- Jun 27, 2013
IPCA Laboratories Ltd. — Marketing Organization
- Jun 27, 2013
AiPing Pharm Inc — Marketing Organization
Indications
Approved for
Studied for
- Abortion, Habitual · Phase 4
- Acute Coronary Syndrome · Phase 4
- Alzheimer Disease · Phase 1
- Aneurysm · Phase 3
- Anticoagulants · Phase 4
- Antiphospholipid Syndrome · Phase 4
- Aortic Valve Disease · Phase 4
- Aortic Valve Insufficiency · Phase 4
- Aortic Valve Stenosis · Phase 4
- Appendix · Phase 4
- Arrhythmias, Cardiac · Phase 3
- Arterial Occlusive Diseases · Phase 3
- Arthritis, Rheumatoid · Phase 1
- Arthroplasty · Phase 4
- Arthroplasty, Replacement, Knee · Phase 2
- Atherosclerosis · Phase 4
- Atrial Flutter · Phase 3
- Blood Coagulation · Phase 4
- Blood Coagulation Disorders · Phase 4
- Blood Loss, Surgical · Phase 4
- Blood Platelets · Phase 4
- Body Weight · Phase 1
- Brain Infarction · Phase 3
- Brain Ischemia · Phase 2/Phase 3
- Cardiomyopathies · Phase 2/Phase 3
- Cardiovascular Diseases · Phase 4
- Carotid Artery Diseases · Phase 3
- Cerebral Infarction · Phase 3
- Cerebral Intraventricular Hemorrhage · Phase 3
- Cerebrovascular Disorders · Phase 4
- Cervix Uteri · Phase 3
- Cognition Disorders · Phase 4
- Colitis, Ulcerative · Phase 1
- Constriction, Pathologic · Phase 3
- Coronary Aneurysm · Phase 3
- Coronary Artery Bypass · Phase 2/Phase 3
- Coronary Artery Disease · Phase 4
- Coronary Disease · Phase 4
- Crohn Disease · Phase 1
- Cytochrome P-450 Enzyme System · Phase 1
- Dementia · Phase 4
- Dermatitis, Atopic · Phase 1
- Diabetes Mellitus · Phase 4
- Diabetes Mellitus, Type 2 · Phase 1
- Drug Interactions · Phase 1
- Drug-Related Side Effects and Adverse Reactions · Phase 3
- Drug Therapy, Combination · Phase 4
- Electric Countershock · Phase 3
- Embolic Stroke · Phase 3
- Embolism · Phase 4
- Embolism and Thrombosis · Phase 2
- Epilepsy · Phase 1
- Esophageal and Gastric Varices · Phase 4
- Essential Hypertension · Phase 1
- Fibrinolytic Agents · Phase 3
- Fibrosis · Phase 4
- Foramen Ovale, Patent · Phase 4
- General Surgery · Phase 4
- Healthy Volunteers · Phase 4
- Heart Defects, Congenital · Phase 4
- Heart Diseases · Phase 4
- Heart Failure · Phase 4
- Heart Valve Diseases · Phase 4
- Heart Valve Prosthesis · Phase 2
- Hematologic Neoplasms · Phase 1
- Hematoma · Phase 4
- Hematoma, Subdural · Phase 3
- Hemorrhage · Phase 4
- Hemostasis · Phase 1
- Hepatitis B, Chronic · Phase 1
- Huntington Disease · Phase 1
- Hypertension · Phase 4
- Hypertension, Portal · Phase 4
- Hypertension, Pulmonary · Phase 3
- Hypertriglyceridemia · Phase 1
- Hypertrophy, Left Ventricular · Phase 4
- Hypoprothrombinemias · Phase 1/Phase 2
- Idiopathic Pulmonary Fibrosis · Phase 3
- Intestinal Neoplasms · Phase 4
- Intracranial Embolism and Thrombosis · Phase 3
- Intracranial Hemorrhage, Hypertensive · Phase 3
- Intracranial Hemorrhages · Phase 3
- Ischemia · Phase 4
- Ischemic Attack, Transient · Phase 4
- Ischemic Stroke · Phase 4
- Kidney Failure, Chronic · Phase 4
- Lipoproteins · Phase 1
- Liver Cirrhosis · Phase 4
- Liver Neoplasms · Phase 4
- Lupus Erythematosus, Systemic · Phase 2/Phase 3
- Lymphoma · Phase 1
- Major Depressive Disorder · Phase 1
- May-Thurner Syndrome · Phase 3
- Melanoma · Phase 1
- MINOCA · Phase 4
- Mitral Valve · Phase 4
- Mitral Valve Annuloplasty · Phase 4
- Mitral Valve Stenosis · Phase 4
- Mucocutaneous Lymph Node Syndrome · Phase 3
- Multiple Sclerosis, Relapsing-Remitting · Phase 3
- Myocardial Infarction · Phase 4
- Myocardial Ischemia · Phase 3
- Neoplasm Metastasis · Phase 1
- Neoplasms · Phase 3
- Non-alcoholic Fatty Liver Disease · Phase 1
- Obesity · Phase 1
- Oligohydramnios · Phase 4
- Osteoarthritis, Knee · Phase 1
- Overweight · Phase 1
- Pancreatic Neoplasms · Early Phase 1
- Parkinson Disease · Phase 1
- Percutaneous Coronary Intervention · Phase 3
- Peripheral Vascular Diseases · Phase 3
- Pharmacokinetics · Phase 1
- Pharmacology · Phase 1
- Portal Vein · Phase 3
- Postoperative Complications · Phase 2/Phase 3
- Postthrombotic Syndrome · Phase 3
- Pregnancy Complications · Phase 3
- Prostatic Neoplasms · Phase 3
- Prostatic Neoplasms, Castration-Resistant · Phase 1
- Prostheses and Implants · Phase 2/Phase 3
- Psoriasis · Phase 1
- Pulmonary Arterial Hypertension · Phase 1
- Pulmonary Embolism · Phase 4
- Renal Insufficiency, Chronic · Phase 4
- Rheumatic Heart Disease · Phase 3
- Rivaroxaban · Phase 3
- Splenectomy · Phase 4
- ST Elevation Myocardial Infarction · Phase 3
- Stroke · Phase 4
- Subarachnoid Hemorrhage · Phase 3
- Thrombocytopenia · Phase 3
- Thromboembolism · Phase 4
- Thrombophlebitis · Phase 3
- Thrombosis · Phase 4
- Upper Extremity Deep Vein Thrombosis · Phase 4
- Urinary Bladder, Overactive · Phase 1
- Vascular Diseases · Phase 3
- Venous Thromboembolism · Phase 3
- Venous Thrombosis · Phase 4
- Vertebral Artery Dissection · Phase 3
- Volunteers · Phase 1
- Warfarin · Phase 3
Mechanism of action
VKORC1 inhibitor
Approval history
- approvedJun 8, 1954
Chemistry & pharmacology
SMILES
CC(=O)CC(C1=CC=CC=C1)C2=C(O)C3=C(OC2=O)C=CC=C3- Mol. weight
- 308.3279 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Racemic Mixture
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral
- Availability
- Discontinued
Oral
Yes
Parenteral
No
Topical
No
Sources
- WikipediaWarfarin ↗
- NCATS5Q7ZVV76EI ↗
- ChEMBLCHEMBL1464 ↗
- ChEMBLCHEMBL1200879 ↗
- ChEMBLCHEMBL1200772 ↗
Also known as
- 4-hydroxy-3-(3-oxo-1-phenylbutyl)coumarin
- 4-hydroxy-3-(3-oxo-1-phenylbutyl)coumarin
- athrombin
- athrombin
- athrombin-k
- athrombin-k
- coumadin
- coumadin
- coumadin
- coumadin
- coumafene
- coumafene
- jantoven
- jantoven
- marevan
- marevan
- marevan
- panwarfin
- panwarfin
- s-warfarin
- s-warfarin
- warfarin
- warfarin
- warfarin
- warfarin
- warfarin
- warfarin
- warfarin
- warfarin
- warfarin
- warfarin
- warfarin potassium
- warfarin potassium
- warfarin potassium
- warfarin potassium
- warfarin sodium
- warfarin sodium
- warfarin sodium
- warfarin sodium
- zoocoumarin
- zoocoumarin
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT07246005 | Phase 2 | Dec 1, 2025 | University of London |
| NCT07128888 | Phase 1 | Nov 17, 2025 | Gan and Lee Pharmaceuticals, USA |
| NCT07081035 | Phase 4 | Oct 31, 2025 | University of Ulsan |
| NCT07068841 | Phase 1 | May 18, 2025 | NeuroDawn Pharmaceutical Co., Ltd. |
| NCT06920056 | Phase 1 | Mar 24, 2025 | Government of China |
| NCT06723691 | Phase 1 | Dec 31, 2024 | Jiangsu ShengDiYa Medicine Co., Ltd. |
| NCT06738992 | Phase 4 | Nov 14, 2024 | Shantou University |
| NCT06686628 | Phase 1 | Nov 13, 2024 | Sanofi |
| NCT06655376 | Phase 4 | Oct 2, 2024 | Columbia University, Cornell University |
| NCT06515730 | Phase 4 | Oct 1, 2024 | Karolinska Institute, Swedish Heart Lung Foundation, The Swedish Research Council |
| NCT06402851 | Phase 4 | Jul 31, 2024 | Daiichi Sankyo, Hospital Sirio-Libanes |
| NCT06772779 | Phase 1 | Apr 1, 2024 | Merck |
| NCT06289504 | Phase 1 | Feb 27, 2024 | Novo Nordisk |
| NCT05995600 | Phase 4 | Dec 31, 2023 | Samjin Pharmaceutical Co., Ltd., Seoul National University |
| NCT04684212 | N/A | Dec 1, 2023 | Henry Ford Health System |
| NCT06145269 | Early Phase 1 (Phase 1) | Dec 1, 2023 | Assiut University |
| NCT06058130 | N/A | Sep 29, 2023 | Zhejiang University |
| NCT07132515 | Phase 4 | Aug 15, 2023 | Mansoura University |
| NCT06335134 | Phase 1 | Jul 14, 2023 | Sciwind Biosciences APAC CO Pty. Ltd., Sichuan University |
| NCT05794399 | Phase 4 | Jun 19, 2023 | Shahid Gangalal National Heart Centre |
Organizations
Research & Development (346)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Boehringer Ingelheim | For profit | 26 | 22 | 5 | 2003 |
| Bayer | For profit | 17 | 11 | 4 | 2004 |
| Bristol-Myers Squibb | For profit | 16 | 5 | 4 | 1998 |
| Johnson and Johnson | For profit | 16 | 9 | 3 | 2004 |
| Daiichi Sankyo | For profit | 12 | 8 | 4 | 2007 |
| Eli Lilly | For profit | 12 | 12 | 1 | 2007 |
| McMaster University | Academic/Hospital | 12 | 5 | 4 | 1998 |
| AstraZeneca | For profit | 11 | 10 | 2 | 2007 |
| Pfizer | For profit | 10 | 4 | 4 | 2002 |
| National Heart, Lung, and Blood Institute (NHLBI) | Government | 8 | 3 | 2 | 1985 |
| Sanofi | For profit | 8 | 6 | 2 | 2002 |
| Astellas | For profit | 7 | 7 | 2 | 2007 |
| Harvard University | Academic/Hospital | 7 | 4 | 4 | 1985 |
| IQVIA | For profit | 6 | 0 | 2 | 2010 |
| University of Utah | Academic/Hospital | 6 | 3 | 4 | 2006 |
| Allegiance Health | Academic/Hospital | 5 | 4 | 3 | 2006 |
| Bial | For profit | 5 | 5 | 1 | 2002 |
| Fudan University | Academic/Hospital | 5 | 3 | 2 | 2015 |
| GlaxoSmithKline | For profit | 5 | 4 | 3 | 2005 |
| Hamilton Health Sciences Corporation | Academic/Hospital | 5 | 5 | 4 | 1998 |
Marketing (20)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Abbott | For profit | NDA2 | Aug 11, 1972 |
| AiPing Pharm Inc | For profit | MKTG | Jun 27, 2013 |
| Amneal Pharmaceuticals | For profit | MKTG | Mar 4, 2013 |
| Aurobindo Pharma | For profit | MKTG | Sep 27, 2004 |
| Barr Laboratories | For profit | MKTG | Mar 26, 1997 |
| Bristol-Myers | For profit | NDA | Jun 8, 1954 |
| Bristol-Myers Squibb | For profit | NDA2 | Jun 8, 1954 |
| Chartwell Pharmaceuticals | For profit | MKTG | Sep 30, 1997 |
| Fosun | For profit | MKTG | Sep 30, 1997 |
| IPCA Laboratories Ltd. | For profit | MKTG | Jun 27, 2013 |
| Invagen Pharms | For profit | MKTG | May 25, 2011 |
| Mylan | For profit | MKTG | Sep 27, 2004 |
| Pharmaceutical Research Associates, Inc. (PRA) | For profit | NDA2 | — |
| Pliva | For profit | MKTG | Jul 5, 2006 |
| Taro Pharmaceuticals | For profit | MKTG | Jul 15, 1999 |
| Taro Pharmaceuticals | For profit | SYN | Jul 15, 1999 |
| Upsher-Smith Laboratories | For profit | MKTG | Oct 2, 2003 |
| Upsher-Smith Laboratories | For profit | SYN | Oct 2, 2003 |
| Watson Pharmaceuticals | For profit | MKTG | — |
| Zydus Discovery DMCC | For profit | MKTG | May 30, 2006 |