phenylbutazone   Click here for help

GtoPdb Ligand ID: 7270

Synonyms: Butazolidine®
Approved drug PDB Ligand Immunopharmacology Ligand
phenylbutazone is an approved drug
Compound class: Synthetic organic
Comment: Phenylbutazone was historically used as a nonsteroidal anti-inflammatory drug (NSAID). Although no longer approved for use in humans, this compound is widely used in animals to reduce muscular damage and inflammation. More recently, phenylbutazone, or 'bute', found notoriety as an illegal contaminant found in some meat samples tested in the European horse meat scandal of 2013. The UK Foods Standards Agency issued this statement regarding bute contamination.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 40.62
Molecular weight 308.15
XLogP 3.71
No. Lipinski's rules broken 0
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Canonical SMILES CCCCC1C(=O)N(N(C1=O)c1ccccc1)c1ccccc1
Isomeric SMILES CCCCC1C(=O)N(N(C1=O)c1ccccc1)c1ccccc1
InChI InChI=1S/C19H20N2O2/c1-2-3-14-17-18(22)20(15-10-6-4-7-11-15)21(19(17)23)16-12-8-5-9-13-16/h4-13,17H,2-3,14H2,1H3
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Summary of Clinical Use Click here for help
US & UK no longer approve clinical use of this drug. Individual national approval agencies may continue to grant marketing authorisation.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
As with other NSAIDs, this drug reduces prostaglandin synthesis by reducing cyclooxegenase (COX) activity.