> Trialight public data. Index of pages: https://trialight.com/llms.txt
> Web page: https://trialight.com/data/asset/warfarin-e500f94c-c2a3-4434-8e09-97345b672b83
> Record changed: 2026-10-13

# Warfarin

Highest phase reached

Approved

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1464)

Drug type

Small molecule

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1464)

First approval year

1954

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1464)

## Development status

**First approval year**

1954

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1464)

**Listing at source**

Listed

**Highest phase reached**

Approved

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1464)

## Names and chemistry

**Drug type**

Small molecule

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1464)

**Drug name**

Warfarin

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1464)

**Molecular weight**

308.33

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1464)

**Structure (SMILES)**

CC(=O)CC(c1ccccc1)c1c(O)c2ccccc2oc1=O

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1464)

### Brand names (2)

- choice
- Choice

### Other names (23)

- 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

## Identifiers

**ATC classification codes**

- B01AA03

Sources for recorded values

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1464)

**CAS registry numbers**

- 81-81-2

**ChEMBL ID**

CHEMBL1464

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1464)

**InChIKey**

PJVWKTKQMONHTI-UHFFFAOYSA-N

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1464)

**PubChem compound IDs**

- 54678486

**RxNorm IDs (RxCUI)**

- 11289

**FDA ingredient codes (UNII)**

- 5Q7ZVV76EI

## Regulatory information

### United States

**Applicant**

BRISTOL MYERS SQUIBB

**Approval date**

8 Jun 1954

**Application number**

NDA009218

### Other regulatory facts

**First in class**

No

**Orphan designation**

No

**Availability**

Prescription only

**Boxed warning**

Yes

## Pharmacology

### Drug classification

**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

### Investigated indications (61)

- **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.

### Open Targets indications (77)

- **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.

### Open Targets warnings (2)

- **Warning**  
Black Box Warning

**Effect**  
carcinogenicity

**Country**  
United States
- **Warning**  
Black Box Warning

**Effect**  
vascular toxicity

**Country**  
United States

### Reported adverse events (40)

- **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.

### Trial references (125)

- NCT00000463  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00000463)
- NCT00000614  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00000614)
- NCT02303795  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT02303795)
- NCT00041938  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00041938)
- NCT03426033  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT03426033)
- NCT00125671  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00125671)
- NCT00216866  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00216866)
- NCT01130025  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT01130025)
- NCT02331095  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT02331095)
- NCT04066764  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT04066764)
- NCT00291330  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00291330)
- NCT00329238  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00329238)
- NCT00680186  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00680186)
- NCT01505881  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT01505881)
- NCT02913326  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT02913326)
- NCT00001713  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00001713)
- NCT00004054  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00004054)
- NCT01911728  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT01911728)
- NCT04676035  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT04676035)
- NCT00004728  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00004728)
- NCT00027066  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00027066)
- NCT00238667  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00238667)
- NCT00262600  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00262600)
- NCT00403767  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00403767)
- NCT01518231  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT01518231)

And 100 more, listed on the interactive page.

## Dosing

**Dose**

2-5mg

**Route**

Oral

**How often**

Initial: once daily; monitor closely; titrate as needed

### Conditions of use (4)

- Adjust dose based on INR response
- Consider genotype and clinical factors for initial dose
- Individualize therapy for each patient
- Monitor INR frequently during initiation

## Chemical properties

**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

## Evidence counts

**Recorded assays**

3,591

**Active assays**

70

### Active assay types (3)

- Confirmatory
- Other
- Summary

## Pharmacologic actions

- Anticoagulants  
Source: [id.nlm.nih.gov](https://id.nlm.nih.gov/mesh/D000925.html)
- Rodenticides  
Source: [id.nlm.nih.gov](https://id.nlm.nih.gov/mesh/D012378.html)

## Biological measurements

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)

- [Thrombotic disease](https://trialight.com/data/condition/thrombotic-disease-3f54ef10-d2ed-524f-a020-8ecb2eb62a52.md)

### In development for (53)

- [Alzheimer disease](https://trialight.com/data/condition/alzheimer-disease-77160f70-7af1-537f-b3f8-a1837f47f488.md) Phase 1
- [Aortic valve stenosis](https://trialight.com/data/condition/aortic-valve-stenosis-d3f1a482-d908-5993-8a6c-7daad057bb89.md) Phase 3
- [Atherosclerosis](https://trialight.com/data/condition/atherosclerosis-5dab64e9-1fd4-5dd2-90c2-ce84935652d1.md) Phase 3
- [Atopic eczema](https://trialight.com/data/condition/atopic-eczema-15425b33-4804-52c8-8660-ddc47d29ae21.md) Phase 1
- [Atrial fibrillation](https://trialight.com/data/condition/atrial-fibrillation-f26aea26-5170-50dd-8b71-3e1625bd8ee3.md) Phase 3
- [Atrial flutter](https://trialight.com/data/condition/atrial-flutter-3a0bf35e-55d4-56e7-a789-e5c7b7fd5dd8.md) Phase 3
- Autoimmune polyendocrinopathy Phase 2
- Brain infarction Phase 3
- [Cancer](https://trialight.com/data/condition/cancer-703b1dfc-4812-50eb-83f4-d7a205d16bdb.md) Phase 1
- [Cardiovascular disorder](https://trialight.com/data/condition/cardiovascular-disorder-362e433e-88a4-575f-90af-50fe7239dec0.md) Phase 3
- Cerebral infarction Phase 3
- [Cirrhosis of liver](https://trialight.com/data/condition/cirrhosis-of-liver-d90e4a84-9e82-54fc-a553-1e42086e8382.md) Phase 2
- [Coronary artery disorder](https://trialight.com/data/condition/coronary-artery-disorder-6f736849-d477-587a-b3fa-b0621d573407.md) Phase 3
- [Crohn disease](https://trialight.com/data/condition/crohn-disease-f7aa2cd8-9680-56b5-858c-2b75f88fb0d0.md) Phase 1
- [Diabetes mellitus](https://trialight.com/data/condition/diabetes-mellitus-1a0391a8-9f84-5600-a2bf-ec97c2229de4.md) Phase 1
- Epilepsy Phase 1
- [Essential hypertension](https://trialight.com/data/condition/essential-hypertension-bd582df2-4596-58b0-aa00-37f10a4759d3.md) Phase 1
- Exocrine pancreatic carcinoma Early phase 1
- Heart disorder Phase 3
- [Heart failure](https://trialight.com/data/condition/heart-failure-e230b1c3-ce91-5f80-b80f-81fc353ce5cc.md) Phase 3

### Other linked conditions (1)

- Metachromatic leukodystrophy

### Targets (1)

- [VKORC1](https://trialight.com/data/target/vkorc1-cc3ba0d2-543f-5d23-8210-88a7efbf0a89.md) Vitamin k epoxide reductase complex subunit 1 isoform 1 inhibitor

---

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