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
1. Look GC, Schullek JR, Holmes CP, Chinn JP, Gordon EM, Gallop MA. (1996)
The identification of cyclooxygenase-1 inhibitors from 4-thiazolidinone combinatorial libraries.
Bioorg Med Chem Lett, 6 (6): 707-712.
2. Wilkerson WW, Copeland RA, Covington M, Trzaskos JM. (1995)
Antiinflammatory 4,5-diarylpyrroles. 2. Activity as a function of cyclooxygenase-2 inhibition.
J Med Chem, 38 (20): 3895-901. [PMID:7562922]