warfarin   

GtoPdb Ligand ID: 6853

Synonyms: Coumadin® | Marevan® | panwarfin
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
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
SMILES / InChI / InChIKey
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
InChI Key PJVWKTKQMONHTI-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1954))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one
International Nonproprietary Names
INN number INN
341 warfarin
Synonyms
Coumadin® | Marevan® | panwarfin
Database Links
CAS Registry No. 81-81-2
ChEMBL Ligand CHEMBL1464
DrugBank Ligand DB00682
DrugCentral Ligand 2847
GtoPdb PubChem SID 178103459
Immunopaedia Search warfarin
PubChem CID 54678486
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Wikipedia Warfarin