Warfarin

Summary

Warfarin (CHEMBL1464) is an approved small molecule (ATC B01AA03) targeting VKORC1; indicated across 61 conditions including thrombotic disease and atrial fibrillation.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: B01AA03
• Targets: 1 (VKORC1)
• Indications: 61 conditions
• Clinical trials: 404
• Chemistry: 308.3 Da · C19H16O4

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1464
Name	Warfarin
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	54678486
ChEBI	CHEBI:87732
ATC	B01AA03
Molecular formula	C19H16O4
Molecular weight	308.3
InChIKey	PJVWKTKQMONHTI-UHFFFAOYSA-N

SMILES: CC(=O)CC(C1=CC=CC=C1)C2=C(C3=CC=CC=C3OC2=O)O

IUPAC name: 4-hydroxy-3-(3-oxo-1-phenylbutyl)chromen-2-one

ChEBI definition: A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.

Also known as: Choice, NSC-59813, Warfarin, Warfarina, Warfarine, warfarine, warfarin, wafarin, SID26748308, SID50085958, SID26754489, WARFARIN

Parent form; salt/anhydrous children: CHEMBL1200772, CHEMBL1200879

Patent coverage: 19,226 distinct patent families (69,797 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 69,728 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
VKORC1	vitamin K epoxide reductase complex subunit 1	Inhibition	5.58	0%	Q9BQB6

Broader ChEMBL bioactivity targets: 10 (assay-derived). Sample: Lysine-specific demethylase 4E, Fructose-bisphosphate aldolase, Vitamin K epoxide reductase complex subunit 1, Beta-lactamase, Proprotein convertase subtilisin/kexin type 7, Albumin, Cytochrome P450 2C9, Aldehyde dehydrogenase 1A1, 3-hydroxyacyl-CoA dehydrogenase type-2, Albumin.

Bioactivity

ChEMBL activities: 9 potent at pChembl ≥ 5 of 18 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
VKORC1	8.06	IC50	8.8	nM	CHEMBL_ACT_19452082
VKORC1	5.97	IC50	1059	nM	CHEMBL_ACT_25646437
ALB	5.7	Kd	2000	nM	CHEMBL_ACT_6187146
P00811	5.45	Potency	3548	nM	CHEMBL_ACT_4679704
ALB	5.33	Kd	4677	nM	CHEMBL_ACT_2158018
ALB	5.27	Kd	5400	nM	CHEMBL_ACT_6187191
ALB	5.26	Kd	5500	nM	CHEMBL_ACT_24422429
ALB	5.26	Kd	5500	nM	CHEMBL_ACT_25832061
P02770	5.03	Kd	9310	nM	CHEMBL_ACT_15458673

Target pathways

Aggregated over 1 target gene(s): VKORC1.

Top Reactome pathways

1 total, by targets touching each:

Pathway	Targets	Genes
Metabolism of vitamin K	1	VKORC1

Dominant GO biological processes

GO term	Targets
xenobiotic metabolic process	1
blood coagulation	1
peptidyl-glutamic acid carboxylation	1
vitamin K metabolic process	1
positive regulation of coagulation	1
bone development	1

Indications & clinical

Indications

61 indications (2 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
thrombotic disease	4	MONDO:0000831	HP:0004419
atrial fibrillation	3	MONDO:0004981	EFO:0000275
cardiovascular disorder	3	MONDO:0004995	EFO:0000319
myocardial infarction	3	MONDO:0005068	EFO:0000612
stroke disorder	3	MONDO:0005098	EFO:0000712
idiopathic pulmonary fibrosis	3	MONDO:0800504	EFO:0000768
heart failure	3	MONDO:0005252	EFO:0003144
heart disorder	3	MONDO:0005267	EFO:0003777
pulmonary embolism	3	MONDO:0005279	EFO:0003827
peripheral vascular disease	3	MONDO:0005294	EFO:0003875
atrial flutter	3	MONDO:0005310	EFO:0003911
relapsing-remitting multiple sclerosis	3	MONDO:0005314	EFO:0003929
venous thromboembolism	3	MONDO:0005399	EFO:0004286
rheumatic heart disease	3	MONDO:0006955	EFO:1001161
myocardial ischemia	3	MONDO:0024644	EFO:1001375
aortic valve stenosis	3	MONDO:0042981	EFO:0000266
atherosclerosis	3	MONDO:0005311	EFO:0003914
thrombocytopenia	3	MONDO:0002049	HP:0001873
cerebral infarction	3	MONDO:0002679	MONDO:0002679
transient ischemic attack	3	MONDO:0005264	EFO:0003764
brain infarction	3	MONDO:0005394	EFO:0004277
coronary artery disorder	3	MONDO:0005010	EFO:0001645
pulmonary arterial hypertension	2	MONDO:0015924	EFO:0001361
cirrhosis of liver	2	MONDO:0005155	EFO:0001422
pulmonary hypertension	2	MONDO:0005149	MONDO:0005149
atopic eczema	1	MONDO:0004980	EFO:0000274
Crohn disease	1	MONDO:0005011	EFO:0000384
diabetes mellitus	1	MONDO:0005015	EFO:0000400
epilepsy	1	MONDO:0005027	EFO:0000474
lymphoma	1	MONDO:0005062	EFO:0000574
neoplasm	1	MONDO:0005070	EFO:0000616
psoriasis	1	MONDO:0005083	EFO:0000676
rheumatoid arthritis	1	MONDO:0008383	EFO:0000685
lymphoid neoplasm	1	MONDO:0005157	EFO:0001642
hypertriglyceridemia	1	MONDO:0005347	EFO:0004211
overactive bladder	1	MONDO:0006624	EFO:1000781
thrombophlebitis	1	MONDO:0002800	HP:0004418
major depressive disorder	1	MONDO:0002009	MONDO:0002009
ulcerative colitis	1	MONDO:0005101	EFO:0000729
metabolic dysfunction-associated steatohepatitis	1	MONDO:0007027	EFO:1001249
obesity disorder	1	MONDO:0011122	EFO:0001073
essential hypertension	1	MONDO:0001134	MONDO:0001134
Alzheimer disease	1	MONDO:0004975	MONDO:0004975
type 2 diabetes mellitus	1	MONDO:0005148	MONDO:0005148
Parkinson disease	1	MONDO:0005180	MONDO:0005180
prostate adenocarcinoma	1	MONDO:0005082	EFO:0000673
melanoma	1	MONDO:0005105	EFO:0000756
osteoarthritis, knee	1	MONDO:0005416	EFO:0004616
exocrine pancreatic carcinoma	0	MONDO:0005192	EFO:0002618

12 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 404.

Phase distribution

Phase	Trials
Not specified	122
PHASE1	94
PHASE3	73
PHASE4	65
PHASE2	42
PHASE2/PHASE3	5
EARLY_PHASE1	2
PHASE1/PHASE2	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT03862859	PHASE4	RECRUITING	The Danish Warfarin-Dialysis Study - Safety and Efficacy of Warfarin in Patients With Atrial Fibrillation on Dialysis
NCT04045093	PHASE4	ACTIVE_NOT_RECRUITING	Dabigatran for Mitral Stenosis Atrial Fibrillation
NCT05643651	PHASE4	RECRUITING	Rivaroxaban for Children Aged Over 2 Years With Giant Coronary Artery Aneurysms After Kawasaki Disease
NCT05782270	PHASE4	RECRUITING	Antithrombotic Therapy After Coronary Artery Bypass Grafting Combined With Coronary Endarterectomy
NCT05794399	PHASE4	RECRUITING	Anticoagulation in Post MI LV Thrombus Trial in Nepal
NCT05995600	PHASE4	RECRUITING	Comparison of Clopidogrel-based Antiplatelet Therapy Versus Warfarin As Secondary Prevention Strategy for AntiPhospholipid Syndrome-related STROKE
NCT06515730	PHASE4	RECRUITING	Treatment With Apixaban Versus Warfarin in Patients With Left Ventricular Thrombus After Acute Myocardial Infarction
NCT06655376	PHASE4	RECRUITING	Aspirin and Hemocompatibility Events in Chronic Advanced Heart Failure Patients With Assist Device
NCT06738992	PHASE4	RECRUITING	Safety and Effectiveness of Early Aspirin Administration After Mitral Valve Repair
NCT06771050	PHASE4	NOT_YET_RECRUITING	Randomised Arthroplasty Infection Worldwide Multidomain Adaptive Platform (ROADMAP) Trial
NCT00245856	PHASE4	COMPLETED	Treatment of Upper Extremity Deep-Vein Thrombosis
NCT00365950	PHASE4	COMPLETED	3 Months’ Versus 6 Months’ Anticoagulation in Patients With DVT and/or PE
NCT00377143	PHASE4	WITHDRAWN	PRospective Evaluation Comparing Initiation of Warfarin StrategiEs (PRECISE): Pharmacogenetic-guided Versus Usual Care
NCT00438230	PHASE4	COMPLETED	Residual Vein Thrombosis Establishes the Optimal Duration of Oral Anticoagulants
NCT00479362	PHASE4	COMPLETED	Anticoagulant Therapy During Pacemaker Implantation
NCT00697151	PHASE4	COMPLETED	Patent Foramen Ovale in Cryptogenic Stroke Study
NCT00964353	PHASE4	COMPLETED	Clinical and Economic Implications of Genetic Testing for Warfarin Management
NCT00993200	PHASE4	COMPLETED	Personalized Medicine Interface Tool (PerMIT): Warfarin: A Trial Comparing Usual Care Warfarin Initiation to PerMIT Pharmacogenetic Guided Warfarin Therapy
NCT01178853	PHASE4	COMPLETED	Drug-Drug Interaction Study to Assess the Effects of Steady State Pitavastatin 4 mg or Rosuvastatin 40 mg on Steady-State Warfarin in Healthy Adult Volunteers
NCT01246011	PHASE4	TERMINATED	Significance of Antibodies to Heparin/Platelet Factor 4 Complex in Vein Graft Patency and Potential Role of Argatroban for Prevention of Vein Graft Occlusion
NCT01438580	PHASE4	COMPLETED	The Effect and Safety of Different Intensity Anticoagulation Therapy in Elderly Patients With Non-valvular Atrial Fibrillation
NCT01452568	PHASE4	COMPLETED	Anticoagulant After Implantation of Biological Aortic Valve Comparing With Aspirin
NCT01569035	PHASE4	TERMINATED	Warfarine in Unexplained Oligohydramnios
NCT01668901	PHASE4	WITHDRAWN	Warfarin Versus Aspirin in Patients With Atrial Fibrillation and Chronic Kidney Disease
NCT01727453	PHASE4	COMPLETED	Compare VKA vs LMWH in Patients With Anticoagulation Criteria and Episode of Gastrointestinal Bleeding.
NCT01747746	PHASE4	COMPLETED	Anticoagulation With Rivaroxaban in Cardioversion -The ARC Study
NCT01994265	PHASE4	COMPLETED	Cognitive Impairment Related to Atrial Fibrillation Prevention Trial
NCT02022527	PHASE4	UNKNOWN	Cost Effectiveness Analysis In Patients With Heart Valve Prosthesis
NCT02054936	PHASE4	WITHDRAWN	Evaluation of Wound Drainage After Knee or Hip Arthroplasty
NCT02090075	PHASE4	COMPLETED	Apixaban Versus Warfarin in the Evaluation of Progression of Atherosclerotic Calcification and Vulnerable Plaque
NCT02161965	PHASE4	COMPLETED	Vascular CalcIfiCation and sTiffness Induced by ORal antIcoAgulation
NCT02206815	PHASE4	COMPLETED	Safety of Ticagrelor+ Warfarinin Comparison With Clopidogrel+Aspirin+Warfarin
NCT02238444	PHASE4	UNKNOWN	Warfarin Prevents Portal Vein Thrombosis in Liver Cirrhotic Patients With Hypersplenism After Laparoscopic Splenectomy
NCT02247414	PHASE4	COMPLETED	Warfarin Prevents Portal Vein Thrombosis in Patients After Laparoscopic Splenectomy and Azygoportal Disconnection
NCT02295475	PHASE4	COMPLETED	Apixaban for Secondary Prevention of Thromboembolism Among Patients With AntiphosPholipid Syndrome
NCT02303171	PHASE4	UNKNOWN	Use of Warfarin After the First Trimester in Pregnant Women With APS
NCT02348723	PHASE4	COMPLETED	Uninterrupted Dabigatran Etexilate in Comparison to Uninterrupted Warfarin in Pulmonary Vein Ablation (RE-CIRCUIT)
NCT02376010	PHASE4	COMPLETED	Rivaroxaban Versus Warfarin in the Evaluation of Progression of Coronary Calcium
NCT02376803	PHASE4	COMPLETED	The Effect of Medication Timing on Anticoagulation Stability in Users of Warfarin: The INRange RCT
NCT02452918	PHASE4	COMPLETED	A Study to Evaluate the Safety of a Single Intravenous (IV) Dose of Orbactiv (Oritavancin) in Participants on Chronic Warfarin Therapy Being Treated For Acute Bacterial Skin and Skin Structure Infection (ABSSSI)

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (5) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

Guideline	Source	Gene(s)	Dosing	Recommendation
Annotation of CPIC Guideline for warfarin and CYP2C9, CYP4F2, VKORC1	CPIC	CYP2C9;CYP4F2;VKORC1	yes	yes
Annotation of CPNDS Guideline for warfarin and CYP2C9, VKORC1	CPNDS	CYP2C9;VKORC1	yes	yes
Annotation of DPWG Guideline for warfarin and VKORC1	DPWG	VKORC1	yes	yes
Annotation of DPWG Guideline for warfarin and CYP2C9	DPWG	CYP2C9	yes	yes
Annotation of RNPGx Guideline for acenocoumarol, fluindione, warfarin	RNPGx	CYP2C9;VKORC1	yes	yes

PharmGKB also curates 90 clinical and 1,220 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

1 molecules share ≥1 primary target. Top 1 by shared-target count:

Molecule	Source	Status	Shared targets
alitretinoin	PubChem	Approved	VKORC1