WARFARIN

Search structure
Synonyms:
Status: Approved (1954)
Entry Type: Small molecule
Molecule Category: Parent
ATC: B01AA03
UNII: 5Q7ZVV76EI

Structure
InChI Key PJVWKTKQMONHTI-UHFFFAOYSA-N
Smile CC(=O)CC(c1ccccc1)c1c(O)c2ccccc2oc1=O
InChI
InChI=1S/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C19H16O4
Molecular Weight 308.33
AlogP 3.61
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 67.51
Molecular species ACID
Aromatic Rings 3.0
Heavy Atoms 23.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 2.6 - EXP
pKa Dissociation Constant 5.08 - EXP
Henry's Law Constant 2.77E-09 atm-m3/mole EST
Atmospheric OH Rate Constant 5.37E-11 cm3/molecule-sec EST
Melting Point 161 deg C EXP
Water Solubility 17 mg/L EXP
Vapor Pressure 1.16E-07 mm Hg EXP

Pharmacology

Primary Target
vitamin K epoxide reductase complex subunit 1
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A2
- - - - 19
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- - - 20000 -
Enzyme Oxidoreductase
- 9 - - -
Enzyme Protease Serine protease Serine protease PA clan Serine protease S1A subfamily
- - - - 18-98
Enzyme Protease Serine protease Serine protease SB clan Serine protease S8B subfamily
- 24590 - - -
Secreted protein
- - 2000-12000 - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 28-122
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 4

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Thrombosis 4 D013927 ClinicalTrials
Aortic Valve Stenosis 3 D001024 ClinicalTrials
Atrial Fibrillation 3 D001281 ClinicalTrials
Myocardial Infarction 3 D009203 ClinicalTrials
Stroke 3 D020521 ClinicalTrials
Idiopathic Pulmonary Fibrosis 3 D054990 ClinicalTrials
Pregnancy 3 D011247 ClinicalTrials
Heart Failure 3 D006333 ClinicalTrials
Heart Diseases 3 D006331 ClinicalTrials
Pulmonary Embolism 3 D011655 ClinicalTrials
Peripheral Vascular Diseases 3 D016491 ClinicalTrials
Venous Thrombosis 3 D020246 ClinicalTrials
Atrial Flutter 3 D001282 ClinicalTrials
Multiple Sclerosis, Relapsing-Remitting 3 D020529 ClinicalTrials
Venous Thromboembolism 3 D054556 ClinicalTrials
Rheumatic Heart Disease 3 D012214 ClinicalTrials
Myocardial Ischemia 3 D017202 ClinicalTrials
Venous Thrombosis 3 D020246 ClinicalTrials
Coronary Disease 3 D003327 ClinicalTrials
Atherosclerosis 3 D050197 ClinicalTrials
Thrombocytopenia 3 D013921 ClinicalTrials
Thromboembolism 3 D013923 ClinicalTrials
Cerebral Infarction 3 D002544 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 3 D064129 ClinicalTrials
Ischemic Attack, Transient 3 D002546 ClinicalTrials
Brain Infarction 3 D020520 ClinicalTrials
Liver Cirrhosis 2 D008103 ClinicalTrials
Hypertension, Pulmonary 2 D006976 ClinicalTrials
Hypertension, Pulmonary 2 D006976 ClinicalTrials
Hemorrhage 2 D006470 ClinicalTrials
Antiphospholipid Syndrome 2 D016736 ClinicalTrials
Colitis, Ulcerative 1 D003093 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Cardiovascular Diseases 1 D002318 ClinicalTrials
Crohn Disease 1 D003424 ClinicalTrials
Diabetes Mellitus 1 D003920 ClinicalTrials
Lymphoma 1 D008223 ClinicalTrials
Alzheimer Disease 1 D000544 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Psoriasis 1 D011565 ClinicalTrials
Arthritis, Rheumatoid 1 D001172 ClinicalTrials
Essential Hypertension 1 D000075222 ClinicalTrials
Thrombophlebitis 1 D013924 ClinicalTrials
Diabetes Mellitus, Type 2 1 D003924 ClinicalTrials
Hematologic Neoplasms 1 D019337 ClinicalTrials
Osteoarthritis 1 D010003 ClinicalTrials
Parkinson Disease 1 D010300 ClinicalTrials
Dermatitis, Atopic 1 D003876 ClinicalTrials
Depressive Disorder, Major 1 D003865 ClinicalTrials
Epilepsy 1 D004827 ClinicalTrials
Hypertriglyceridemia 1 D015228 ClinicalTrials
Non-alcoholic Fatty Liver Disease 1 D065626 ClinicalTrials
Nausea 1 D009325 ClinicalTrials
Urinary Bladder, Overactive 1 D053201 ClinicalTrials
Ischemic Stroke 1 D000083242 ClinicalTrials
Pancreatic Neoplasms 0 D010190 ClinicalTrials

Related Entries

Scaffolds

Salt
Salt

Cross References

Resources Reference
CAS NUMBER 81-81-2
ChEBI 87732
ChEMBL CHEMBL1464
DrugBank DB00682
DrugCentral 2847
EPA CompTox DTXSID5023742
FDA SRS 5Q7ZVV76EI
Human Metabolome Database HMDB0001935
Guide to Pharmacology 6853
KEGG C01541
PubChem 54678486
SureChEMBL SCHEMBL3689
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