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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCCCC1C(=O)N(C2=CC=CC=C2)N(C3=CC=CC=C3)C1=O
Isomeric SMILES CCCCC1C(=O)N(N(C1=O)C2=CC=CC=C2)C3=CC=CC=C3
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
InChI Key VYMDGNCVAMGZFE-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Non-steroidal anti-inflammatory ligands
Approved drug? Yes
Withdrawn drug? Yes
IUPAC Name Click here for help
4-butyl-1,2-diphenylpyrazolidine-3,5-dione
International Nonproprietary Names Click here for help
INN number INN
4 phenylbutazone
Synonyms Click here for help
Butazolidine®
Database Links Click here for help
CAS Registry No. 50-33-9
ChEMBL Ligand CHEMBL101
DrugBank Ligand DB00812
DrugCentral Ligand 2145
GtoPdb PubChem SID 178103844
PubChem CID 4781
RCSB PDB Ligand P1Z
Search Google for chemical match using the InChIKey VYMDGNCVAMGZFE-UHFFFAOYSA-N
Search Google for chemicals with the same backbone VYMDGNCVAMGZFE
Search PubMed clinical trials phenylbutazone
Search PubMed titles phenylbutazone
Search PubMed titles/abstracts phenylbutazone
UniChem Compound Search for chemical match using the InChIKey VYMDGNCVAMGZFE-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey VYMDGNCVAMGZFE-UHFFFAOYSA-N
Wikipedia Phenylbutazone