Warfarin
Highest phase reached
Approved
Drug type
Small molecule
First approval year
1954
- First approval year
- 1954
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Warfarin
- Molecular weight
- 308.33
- Structure (SMILES)
- CC(=O)CC(c1ccccc1)c1c(O)c2ccccc2oc1=O
- choice
- Choice
- coumadine warfarine
- nsc 59813
- NSC-59813
- warfarin
- Warfarin
- WARFARIN [HSDB]
- warfarin [INN]
- WARFARIN [ISO]
- WARFARIN [MI]
- WARFARIN [USP-RS]
- WARFARIN [VANDF]
- Warfarin [WHO-DD]
- warfarin hsdb
- warfarin inn
- warfarin iso
- warfarin mi
- warfarin usp rs
- warfarin vandf
- warfarin who dd
- warfarina
- Warfarina
- warfarine
- Warfarine
- ATC classification codes
- B01AA03
Sources for recorded values
- CAS registry numbers
- 81-81-2
- ChEMBL ID
- CHEMBL1464
- InChIKey
- PJVWKTKQMONHTI-UHFFFAOYSA-N
- PubChem compound IDs
- 54678486
- RxNorm IDs (RxCUI)
- 11289
- FDA ingredient codes (UNII)
- 5Q7ZVV76EI
- Applicant
- BRISTOL MYERS SQUIBB
- Approval date
- 8 Jun 1954
- Application number
- NDA009218
- First in class
- No
- Orphan designation
- No
- Availability
- Prescription only
- Boxed warning
- Yes
- Pharmacology name
- warfarin
- Type
- Synthetic organic
- Drug name stem
- -farin
- Approval recorded by Guide to Pharmacology
- Yes
Administration routes
- Oral
- Parenteral
Mechanisms of action
- Action
- Inhibition
- Action type
- Inhibitor
- Target
- vitamin K epoxide reductase complex subunit 1
- Gene symbol
- VKORC1
- Protein identifier
- Q9BQB6
- Median affinity
- 5.58
- Affinity units
- pKi
- Primary target
- Yes
Open Targets mechanisms
- Mechanism
- Vitamin k epoxide reductase complex subunit 1 isoform 1 inhibitor
- Action type
- Inhibitor
- Target
- Vitamin K epoxide reductase complex subunit 1
DrugCentral mechanisms
- Action type
- Inhibitor
- Gene symbol
- VKORC1
- Protein identifier
- Q9BQB6
- Organism
- Homo sapiens
- Target development level
- Clinical
- Condition
- Aortic Valve Stenosis
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000266
- Subject identifier
- D001024
- Condition
- Dermatitis, Atopic
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000274
- Subject identifier
- D003876
- Condition
- Atrial Fibrillation
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000275
- Subject identifier
- D001281
- Condition
- Cardiovascular Diseases
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000319
- Subject identifier
- D002318
- Condition
- Crohn Disease
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000384
- Subject identifier
- D003424
- Condition
- Diabetes Mellitus
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000400
- Subject identifier
- D003920
- Condition
- Epilepsy
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000474
- Subject identifier
- D004827
- Condition
- Lymphoma
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000574
- Subject identifier
- D008223
- Condition
- Myocardial Infarction
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000612
- Subject identifier
- D009203
- Condition
- Neoplasms
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000616
- Subject identifier
- D009369
- Condition
- Prostatic Neoplasms
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000673
- Subject identifier
- D011471
- Condition
- Psoriasis
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000676
- Subject identifier
- D011565
- Condition
- Arthritis, Rheumatoid
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000685
- Subject identifier
- D001172
- Condition
- Stroke
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000712
- Subject identifier
- D020521
- Condition
- Colitis, Ulcerative
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000729
- Subject identifier
- D003093
- Condition
- Melanoma
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000756
- Subject identifier
- D008545
- Condition
- Idiopathic Pulmonary Fibrosis
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000768
- Subject identifier
- D054990
- Condition
- Obesity
- Highest recorded phase
- 1
- Condition identifier
- EFO:0001073
- Subject identifier
- D009765
- Condition
- Hypertension, Pulmonary
- Highest recorded phase
- 2
- Condition identifier
- EFO:0001361
- Subject identifier
- D006976
- Condition
- Liver Cirrhosis
- Highest recorded phase
- 2
- Condition identifier
- EFO:0001422
- Subject identifier
- D008103
- Condition
- Hematologic Neoplasms
- Highest recorded phase
- 1
- Condition identifier
- EFO:0001642
- Subject identifier
- D019337
- Condition
- Coronary Disease
- Highest recorded phase
- 3
- Condition identifier
- EFO:0001645
- Subject identifier
- D003327
- Condition
- Pancreatic Neoplasms
- Highest recorded phase
- 0.5
- Condition identifier
- EFO:0002618
- Subject identifier
- D010190
- Condition
- Pregnancy
- Highest recorded phase
- 3
- Condition identifier
- EFO:0002950
- Subject identifier
- D011247
- Condition
- Heart Failure
- Highest recorded phase
- 3
- Condition identifier
- EFO:0003144
- Subject identifier
- D006333
And 36 more, listed on the interactive page.
- Condition identifier
- EFO_0000275
- Condition identifier
- EFO_0000319
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000474
- Highest recorded phase
- 1
- Condition identifier
- EFO_0000551
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000612
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000616
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000712
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000756
- Highest recorded phase
- 1
- Condition identifier
- EFO_0000768
- Highest recorded phase
- 3
- Condition identifier
- EFO_0001361
- Highest recorded phase
- 2
- Condition identifier
- EFO_0001422
- Highest recorded phase
- 2
- Condition identifier
- EFO_0001642
- Highest recorded phase
- 1
- Condition identifier
- EFO_0002618
- Condition identifier
- EFO_0002950
- Highest recorded phase
- 3
- Condition identifier
- EFO_0003144
- Condition identifier
- EFO_0003777
- Highest recorded phase
- 3
- Condition identifier
- EFO_0003827
- Highest recorded phase
- 3
- Condition identifier
- EFO_0003875
- Highest recorded phase
- 3
- Condition identifier
- EFO_0003906
- Condition identifier
- EFO_0003907
- Highest recorded phase
- 3
- Condition identifier
- EFO_0003911
- Highest recorded phase
- 3
- Condition identifier
- EFO_0003929
- Highest recorded phase
- 3
- Condition identifier
- EFO_0004286
- Highest recorded phase
- 3
- Condition identifier
- EFO_0008585
- Highest recorded phase
- 3
- Condition identifier
- EFO_0009551
- Highest recorded phase
- 2
And 52 more, listed on the interactive page.
- Warning
- Black Box Warning
- Effect
- carcinogenicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- vascular toxicity
- Country
- United States
- Event
- abdominal wall haematoma
- Reports
- 173
- Reporting signal score
- 503.302
- Event
- anaemia
- Reports
- 1,601
- Reporting signal score
- 1,385.17
- Event
- calciphylaxis
- Reports
- 461
- Reporting signal score
- 1,826.17
- Event
- cerebral haemorrhage
- Reports
- 384
- Reporting signal score
- 591.382
- Event
- coagulopathy
- Reports
- 401
- Reporting signal score
- 809.801
- Event
- contusion
- Reports
- 403
- Reporting signal score
- 286.333
- Event
- drug interaction
- Reports
- 1,791
- Reporting signal score
- 1,867.37
- Event
- ecchymosis
- Reports
- 196
- Reporting signal score
- 371.855
- Event
- epistaxis
- Reports
- 847
- Reporting signal score
- 1,138.11
- Event
- faeces discoloured
- Reports
- 291
- Reporting signal score
- 453.291
- Event
- gastric haemorrhage
- Reports
- 950
- Reporting signal score
- 2,891.89
- Event
- gastrointestinal haemorrhage
- Reports
- 1,663
- Reporting signal score
- 2,860.71
- Event
- haematemesis
- Reports
- 339
- Reporting signal score
- 449.955
- Event
- haematochezia
- Reports
- 355
- Reporting signal score
- 344.771
- Event
- haematocrit decreased
- Reports
- 373
- Reporting signal score
- 554.373
- Event
- haematoma
- Reports
- 990
- Reporting signal score
- 2,172.46
- Event
- haematuria
- Reports
- 907
- Reporting signal score
- 1,651.77
- Event
- haemoglobin decreased
- Reports
- 1,115
- Reporting signal score
- 1,190.98
- Event
- haemoptysis
- Reports
- 384
- Reporting signal score
- 567.722
- Event
- haemorrhage
- Reports
- 1,726
- Reporting signal score
- 3,172.79
- Event
- haemorrhage intracranial
- Reports
- 653
- Reporting signal score
- 1,622.79
- Event
- international normalised ratio abnormal
- Reports
- 675
- Reporting signal score
- 2,403.89
- Event
- international normalised ratio decreased
- Reports
- 532
- Reporting signal score
- 1,762
- Event
- international normalised ratio fluctuation
- Reports
- 198
- Reporting signal score
- 648.866
- Event
- international normalised ratio increased
- Reports
- 5,098
- Reporting signal score
- 18,251.1
And 15 more, listed on the interactive page.
- NCT00000463
- NCT00000614
- NCT02303795
- NCT00041938
- NCT03426033
- NCT00125671
- NCT00216866
- NCT01130025
- NCT02331095
- NCT04066764
- NCT00291330
- NCT00329238
- NCT00680186
- NCT01505881
- NCT02913326
- NCT00001713
- NCT00004054
- NCT01911728
- NCT04676035
- NCT00004728
- NCT00027066
- NCT00238667
- NCT00262600
- NCT00403767
- NCT01518231
And 100 more, listed on the interactive page.
- Dose
- 2-5mg
- Route
- Oral
- How often
- Initial: once daily; monitor closely; titrate as needed
- Adjust dose based on INR response
- Consider genotype and clinical factors for initial dose
- Individualize therapy for each patient
- Monitor INR frequently during initiation
- Hydrogen bond acceptors
- 4
- Hydrogen bond donors
- 1
- Polar surface area
- 67.51
- Calculated partition coefficient (ALogP)
- 3.61
- Calculated partition coefficient (XLogP)
- 2.7
- Prodrug
- No
- Chirality
- Racemic
- Inorganic
- No
- Rule-of-five violations
- 0
- Rotatable bonds
- 4
- Heavy atoms
- 23
- Molecular formula
- C19H16O4
- Monoisotopic mass
- 308.10485899
- Natural product
- Yes
- Recorded assays
- 3,591
- Active assays
- 70
- Confirmatory
- Other
- Summary
- Anticoagulants
- Rodenticides
These details could not be displayed.
Related records
Trials (483)
- "ORBIT" Versus "HAS-BLED" Scores in Predicting Major Bleeding in Patients With Atrial Fibrillation Receiving Oral Anticoagulants.
- 3 Months' Versus 6 Months' Anticoagulation in Patients With DVT and/or PE
- A Clinical Study to Determine the Effect of YM178 on the Pharmacokinetics of Warfarin in Healthy Subjects
- A Clinical Trial Comparing Efficacy and Safety of Dabigatran Etexilate With Warfarin in Patients With Cerebral Venous and Dural Sinus Thrombosis (RE-SPECT CVT)
- A Clinical Trial to Evaluate the Effect of Fimarsartan on Pharmacodynamics, Pharmacokinetics, and the Safety of Warfarin in Healthy Male Volunteers
- A Comparative Study of the Treatment of Real-world Patients With Clear Cell Carcinoma of the Ovary
- A Dose Response Study of Dabigatran Etexilate(BIBR 1048) in Pharmacodynamics and Safety in Patients With Non-valvular Atrial Fibrillation in Comparison to Warfarin
- A Drug Drug Interaciton Study of Imrecoxib and Warfarin in Healthy Volunteers
- A Drug Interaction Study of Danicopan
- A Drug Interaction Study of Lanabecestat (LY3314814) and Warfarin in Healthy Participants
- A Drug Interaction Study of LY3871801 in Healthy Participants
- A Drug Interaction Study of Warfarin and Canagliflozin in Healthy Adult Volunteers
- A Drug Interaction Study to Assess the Effect of LY317615 on the Metabolic Pathway of Warfarin
- A Drug Interaction Study With Albiglutide and Warfarin
- A Drug-Drug Interaction (DDI) Study of LY3437943 in Obese Participants
- A Drug-Drug Interaction Study Between AZD9668 and Warfarin to Study the Effect of AZD9668 on the Metabolism and Effect of Warfarin
- A Drug-Drug Interaction Study Between XW003 and Metformin, Warfarin, Rosuvastatin or Digoxin
- A Drug-Drug Interaction Study of HDM1002 and Metformin, Empagliflozin, Midazolam, Valsartan, and Warfarin
- A Drug-Drug Interaction Study of Warfarin and PA21
- A Drug-Drug Interaction Study to Study the Effect of AZD1981 on Warfarin
Approved for (1)
In development for (53)
- Alzheimer disease Phase 1
- Aortic valve stenosis Phase 3
- Atherosclerosis Phase 3
- Atopic eczema Phase 1
- Atrial fibrillation Phase 3
- Atrial flutter Phase 3
- Autoimmune polyendocrinopathy Phase 2
- Brain infarction Phase 3
- Cancer Phase 1
- Cardiovascular disorder Phase 3
- Cerebral infarction Phase 3
- Cirrhosis of liver Phase 2
- Coronary artery disorder Phase 3
- Crohn disease Phase 1
- Diabetes mellitus Phase 1
- Epilepsy Phase 1
- Essential hypertension Phase 1
- Exocrine pancreatic carcinoma Early phase 1
- Heart disorder Phase 3
- Heart failure Phase 3
Other linked conditions (1)
- Metachromatic leukodystrophy
Targets (1)
- VKORC1 Vitamin k epoxide reductase complex subunit 1 isoform 1 inhibitor