warfarin

Trade name: coumadin

Small moleculeapproved

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

Phase 1
119
Phase 2
129
Phase 3
94
Phase 4
85

Earliest trial started Jul 1, 1985 (NCT00000517)

Timeline

1950s

  1. Jun 8, 1954

    Bristol-Myers — Earliest FDA Approval

  2. Jun 8, 1954

    Bristol-Myers Squibb — NDA Secondary Org

  3. Jun 8, 1954

    Bristol-Myers — NDA Organization

1970s

  1. Aug 11, 1972

    Abbott — NDA Secondary Org

1980s

  1. Jan 1, 1985

    Earliest Phase 3 Sponsor(trial)

1990s

  1. Mar 26, 1997

    Barr Laboratories — Marketing Organization

  2. Sep 30, 1997

    Chartwell Pharmaceuticals — Marketing Organization

  3. Sep 30, 1997

    Fosun — Marketing Organization

  4. Jan 1, 1998

    Earliest Phase 1 Sponsor(trial)

  5. Jul 15, 1999

    Taro Pharmaceuticals — Marketing Organization

2000s

  1. Jan 1, 2000

    Earliest Phase 2 Sponsor(trial)

  2. Oct 2, 2003

    Upsher-Smith Laboratories — Marketing Organization

  3. Sep 27, 2004

    Aurobindo Pharma — Marketing Organization

  4. Sep 27, 2004

    Mylan — Marketing Organization

  5. May 30, 2006

    Zydus Discovery DMCC — Marketing Organization

  6. Jul 5, 2006

    Pliva — Marketing Organization

2010s

  1. May 25, 2011

    Invagen Pharms — Marketing Organization

  2. Mar 4, 2013

    Amneal Pharmaceuticals — Marketing Organization

  3. Jun 27, 2013

    IPCA Laboratories Ltd. — Marketing Organization

  4. Jun 27, 2013

    AiPing Pharm Inc — Marketing Organization

Indications

Studied for

Mechanism of action

Approval history

  • approvedJun 8, 1954

Chemistry & pharmacology

Loading structure…

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

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 IDPhaseStart dateSponsor(s)
NCT07246005Phase 2Dec 1, 2025University of London
NCT07128888Phase 1Nov 17, 2025Gan and Lee Pharmaceuticals, USA
NCT07081035Phase 4Oct 31, 2025University of Ulsan
NCT07068841Phase 1May 18, 2025NeuroDawn Pharmaceutical Co., Ltd.
NCT06920056Phase 1Mar 24, 2025Government of China
NCT06723691Phase 1Dec 31, 2024Jiangsu ShengDiYa Medicine Co., Ltd.
NCT06738992Phase 4Nov 14, 2024Shantou University
NCT06686628Phase 1Nov 13, 2024Sanofi
NCT06655376Phase 4Oct 2, 2024Columbia University, Cornell University
NCT06515730Phase 4Oct 1, 2024Karolinska Institute, Swedish Heart Lung Foundation, The Swedish Research Council
NCT06402851Phase 4Jul 31, 2024Daiichi Sankyo, Hospital Sirio-Libanes
NCT06772779Phase 1Apr 1, 2024Merck
NCT06289504Phase 1Feb 27, 2024Novo Nordisk
NCT05995600Phase 4Dec 31, 2023Samjin Pharmaceutical Co., Ltd., Seoul National University
NCT04684212N/ADec 1, 2023Henry Ford Health System
NCT06145269Early Phase 1 (Phase 1)Dec 1, 2023Assiut University
NCT06058130N/ASep 29, 2023Zhejiang University
NCT07132515Phase 4Aug 15, 2023Mansoura University
NCT06335134Phase 1Jul 14, 2023Sciwind Biosciences APAC CO Pty. Ltd., Sichuan University
NCT05794399Phase 4Jun 19, 2023Shahid Gangalal National Heart Centre
Showing 20 of 393 trials
Page 1 / 20

Organizations

Research & Development (346)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Boehringer IngelheimFor profit262252003
BayerFor profit171142004
Bristol-Myers SquibbFor profit16541998
Johnson and JohnsonFor profit16932004
Daiichi SankyoFor profit12842007
Eli LillyFor profit121212007
McMaster UniversityAcademic/Hospital12541998
AstraZenecaFor profit111022007
PfizerFor profit10442002
National Heart, Lung, and Blood Institute (NHLBI)Government8321985
SanofiFor profit8622002
AstellasFor profit7722007
Harvard UniversityAcademic/Hospital7441985
IQVIAFor profit6022010
University of UtahAcademic/Hospital6342006
Allegiance HealthAcademic/Hospital5432006
BialFor profit5512002
Fudan UniversityAcademic/Hospital5322015
GlaxoSmithKlineFor profit5432005
Hamilton Health Sciences CorporationAcademic/Hospital5541998
346 organizations
Page 1 / 18

Marketing (20)

OrganizationOrg typeRelationshipDate
AbbottFor profitNDA2Aug 11, 1972
AiPing Pharm IncFor profitMKTGJun 27, 2013
Amneal PharmaceuticalsFor profitMKTGMar 4, 2013
Aurobindo PharmaFor profitMKTGSep 27, 2004
Barr LaboratoriesFor profitMKTGMar 26, 1997
Bristol-MyersFor profitNDAJun 8, 1954
Bristol-Myers SquibbFor profitNDA2Jun 8, 1954
Chartwell PharmaceuticalsFor profitMKTGSep 30, 1997
FosunFor profitMKTGSep 30, 1997
IPCA Laboratories Ltd.For profitMKTGJun 27, 2013
Invagen PharmsFor profitMKTGMay 25, 2011
MylanFor profitMKTGSep 27, 2004
Pharmaceutical Research Associates, Inc. (PRA)For profitNDA2
PlivaFor profitMKTGJul 5, 2006
Taro PharmaceuticalsFor profitMKTGJul 15, 1999
Taro PharmaceuticalsFor profitSYNJul 15, 1999
Upsher-Smith LaboratoriesFor profitMKTGOct 2, 2003
Upsher-Smith LaboratoriesFor profitSYNOct 2, 2003
Watson PharmaceuticalsFor profitMKTG
Zydus Discovery DMCCFor profitMKTGMay 30, 2006