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Compound Detail

CHEMBL1464

WARFARIN
💊 Approved Drug
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💊 Approved Drug
CC(=O)CC(c1ccccc1)c1c(O)c2ccccc2oc1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1464
Name WARFARIN
Phase Approved
Structure Type MOL
InChI Key PJVWKTKQMONHTI-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Choice NSC-59813 Warfarin Warfarina Warfarine
8
Targets
24
Activities
4
Assay Types
30
PK Parameters
20
Publications
5
Known Names
20
Indications

Molecular Properties

308.3
MW (Da)
3.61
ALogP
4
HBA
1
HBD
67.5
PSA (Ų)
0.75
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1954
Availability Prescription
Chirality Racemic

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -farin

Extended Properties

Molecular Formula C19H16O4
MW 308.33
Aromatic Rings 3
Heavy Atoms 23
NP-Likeness 0.39

Indications

Thrombosis Thrombosis Aortic Valve Stenosis Atherosclerosis Atrial Fibrillation Atrial Flutter Brain Infarction Cardiovascular Diseases Cerebral Infarction Coronary Disease Heart Diseases Heart Failure Idiopathic Pulmonary Fibrosis Ischemic Attack, Transient Multiple Sclerosis, Relapsing-Remitting Myocardial Infarction Myocardial Ischemia Peripheral Vascular Diseases Pregnancy Prostatic Neoplasms, Castration-Resistant

ATC Classification

B01AA03
warfarin
Level 1: BLOOD AND BLOOD FORMING ORGANS
Level 2: ANTITHROMBOTIC AGENTS

Activity Summary

Kd 13 meas. best 5.7
IC50 9 meas. best 8.08
EC50 1 meas. best 4.05
Ki 1 meas. best 4.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 8.08 6.0867 8.3 3
Vitamin K epoxide reductase complex subunit 1
CHEMBL1930
 IC50 8.06 7.015 8.8 2
Albumin
CHEMBL3253
 Kd 5.7 5.29 2000.0 6
Unchecked
CHEMBL612545
 Kd 5.05 5.05 9000.0 1
Albumin
CHEMBL4817
 Kd 5.03 4.5833 9310.0 3
Cytochrome P450 2C9
CHEMBL3397
 Ki 4.7 4.7 20000.0 1
Proprotein convertase subtilisin/kexin type 7
CHEMBL2232
 IC50 4.61 4.61 24590.0 1
NALM-6
CHEMBL614187
 IC50 4.13 4.13 74800.0 1
ADMET
CHEMBL612558
 Kd 4.09 4.09 81400.0 1
Unchecked
CHEMBL612545
 EC50 4.05 4.05 89600.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.16 mL.min-1.kg-1 Homo sapiens
CL 0.055 mL.min-1.kg-1 Homo sapiens
CL 0.055 mL.min-1.kg-1 Homo sapiens
CL 0.1 mL.min-1.kg-1 Homo sapiens
CL 0.04 mL.min-1.kg-1 Homo sapiens
CL 0.13 mL.min-1.kg-1 Macaca
CL 0.055 mL.min-1.kg-1 Homo sapiens
CL 0.3 mL.min-1.kg-1 Canis lupus familiaris
CL 0.36 mL.min-1.kg-1 Rattus norvegicus
CL - mL.min-1.kg-1 Mus musculus
CL 6.0 mL.min-1.kg-1 Mus musculus
CL - mL.min-1.kg-1 Homo sapiens
CL - mL.min-1.g-1 Homo sapiens
CL - mL.min-1.g-1 Homo sapiens
CL - mL.min-1.g-1 Mus musculus
CL - mL.min-1.g-1 Mus musculus
CL 5.25 mL.min-1.g-1 Homo sapiens
CL 3.0 uL.min-1.(10^6cells)-1 Homo sapiens
CL 7.9 mL.min-1.g-1 Mus musculus
CL 30.9 mL.min-1.kg-1 Mus musculus
CL 23.0 mL.min-1.kg-1 Mus musculus
CL - mL.min-1.g-1 Homo sapiens
CL 3e-06 mL.min-1.g-1 Homo sapiens
CL 0.003 uL/min Homo sapiens
CL 0.3 mL.min-1.g-1 Homo sapiens
CL - mL.min-1.g-1 Homo sapiens
CL 9.6 mL.min-1.g-1 Homo sapiens
CL 9.6 mL.min-1.g-1 Homo sapiens
CL 9.6 mL.min-1.g-1 Homo sapiens
CL 9.6 mL.min-1.g-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 8.32 nM 8.08 Inhibition of pepsin from porcine gastric mucosa using Arg-Glu-(EDANS)- Ser-Gln-... 21510613
Vitamin K epoxide reductase complex subunit 1 IC50 = 8.8 nM 8.06 Inhibition of VKOR (unknown origin) in HEK293 expressing FIXgla-PC incubated for... 31147103
Vitamin K epoxide reductase complex subunit 1 IC50 = 1059.0 nM 5.97 Inhibition of recombinant human wild-type VKORC1 expressed in Pichia pastoris me... 37741121
Albumin Kd = 2000.0 nM 5.7 Binding affinity to human serum albumin at 20 degC by isothermal titration calor... 21438527
Unchecked IC50 = 2200.0 nM 5.66 Inhibition of rat microsomal VKER 17275317
Albumin Kd = 4677.35 nM 5.33 Binding affinity to human serum albumin by PAMPA method 18348514
Albumin Kd = 5400.0 nM 5.27 Binding affinity to low-affinity binding site of human serum albumin at 20 degC ... 21438527
Albumin Kd = 5500.0 nM 5.26 Binding affinity to human serum albumin assessed as dissociation rate constant b... 35195417
Albumin Kd = 5500.0 nM 5.26 Binding affinity to human serum albumin assessed as equilibrium dissociation con... 38579622
Unchecked Kd = 9000.0 nM 5.05 The compound was estimated for biosensor analysis 10821711
Albumin Kd = 9310.0 nM 5.03 Binding affinity to Wistar rat serum albumin 21071520
Albumin Kd = 12000.0 nM 4.92 Binding affinity to human serum albumin at 37 degC by surface plasmon resonance ... 21438527
Albumin Kd = 20000.0 nM 4.7 Binding affinity to low-affinity binding site of rat serum albumin at 20 degC by... 21438527
Cytochrome P450 2C9 Ki = 20000.0 nM 4.7 Binding affinity towards cytochrome P450 2C9 14761192
Proprotein convertase subtilisin/kexin type 7 IC50 = 24590.0 nM 4.61 Inhibition of recombinant type 8 subtilisin using Arg-Glu-(EDANS)- Ser-Gln-Asn-T... 21510613
Unchecked IC50 = 30000.0 nM 4.52 Inhibition of HIV protease 27484512
NALM-6 IC50 = 74800.0 nM 4.13 Cytotoxicity against Homo sapiens (human) NALM6 cells assessed as reduction in c... -
ADMET Kd = 81400.0 nM 4.09 Binding affinity to Wistar rat brain lipid by TRANSIL assay 21071520
Unchecked EC50 = 89600.0 nM 4.05 Displacement of [3H](S)-warfarin from methacrylic acid-ethylene dimethacrylate c... 20973485
Albumin Kd = 95000.0 nM 4.02 Binding affinity to rat serum albumin at 37 degC by surface plasmon resonance as... 21438527

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 346
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 67
16472241 10.2174/1570163043334794 Hepatotoxicity 18
24602787 10.1016/j.ejmech.2014.02.003 ADMET 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
10821711 10.1021/jm991174y Albumin 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
22633008 10.1016/j.ejmech.2012.04.036 Rattus norvegicus 9
22633008 10.1016/j.ejmech.2012.04.036 Plasma 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
15920768 10.1002/jps.20373 ADMET 8
14741253 10.1016/j.bmcl.2003.11.060 Unchecked 7
21438527 10.1021/jm1008924 Albumin 7
28436655 10.1021/acs.jmedchem.7b00392 ADMET 7
20167480 10.1016/j.bmcl.2010.01.123 Rattus norvegicus 6
- 10.6019/CHEMBL3301361 ADMET 6
25580906 10.1021/jm5015742 ADMET 5
21474681 10.1124/dmd.111.038778 Brain 5

Data from ChEMBL 36 via Core Engine