warfarin   Click here for help

GtoPdb Ligand ID: 6853

Synonyms: Coumadin® | Marevan® | panwarfin
Approved drug
warfarin is an approved drug (FDA (1954))
Compound class: Synthetic organic
Comment: PubChem CID 54678486 is an enatiomeric mixture of the much more active S-form (CID 54688261) and the R-form (CID 54684598) [2]. This reference also reviews important pharmacogenomic aspects of this drug but note the application of this has become controversial (see the PharmKB drug link). Note also there is also a tautomeric variant depicted as CID 54689812. Marketed formulations may specify warfarin sodium (CID 16204922) or warfarin potassium (CID 23706212).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 67.51
Molecular weight 308.1
XLogP 3.6
No. Lipinski's rules broken 0
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Canonical SMILES CC(=O)CC(c1c(=O)oc2c(c1O)cccc2)c1ccccc1
Isomeric SMILES CC(=O)CC(c1c(=O)oc2c(c1O)cccc2)c1ccccc1
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
No information available.
Summary of Clinical Use Click here for help
Used in the treatment of pulmonary embolism, cerebral embolism, cardiomyopathy, retinal vascular occusion, atrial fibrilation and flutter, transient cerebral ischaemia, arterial embolism and thrombosis.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
An anticoagulant drug which acts to inhibit vitamin-K dependent synthesis of biologically active forms of various clotting factors and regulatory factors. This is achieved by inhibition of vitamin K epoxide reductase complex subunit 1 isoform 1 (VKORC1).
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