celecoxib   Click here for help

GtoPdb Ligand ID: 2892

Synonyms: Celecox® | Elyxyb® (DFN-15; oral solution) | Onsenal® | SC-58635 [4] | SC58635
Approved drug PDB Ligand Immunopharmacology Ligand
celecoxib is an approved drug (FDA (1998))
Compound class: Synthetic organic
Comment: Celecoxib is a non-steroidal anti-inflammatory drug (NSAID) [4].
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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

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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 1
Rotatable bonds 4
Topological polar surface area 85.84
Molecular weight 381.08
XLogP 3.89
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 Cc1ccc(cc1)c1cc(nn1c1ccc(cc1)S(=O)(=O)N)C(F)(F)F
Isomeric SMILES Cc1ccc(cc1)c1cc(nn1c1ccc(cc1)S(=O)(=O)N)C(F)(F)F
InChI InChI=1S/C17H14F3N3O2S/c1-11-2-4-12(5-3-11)15-10-16(17(18,19)20)22-23(15)13-6-8-14(9-7-13)26(21,24)25/h2-10H,1H3,(H2,21,24,25)
InChI Key RZEKVGVHFLEQIL-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Non-steroidal anti-inflammatory ligands
Approved drug? Yes (FDA (1998))
IUPAC Name Click here for help
4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
International Nonproprietary Names Click here for help
INN number INN
7767 celecoxib
Synonyms Click here for help
Celecox® | Elyxyb® (DFN-15; oral solution) | Onsenal® | SC-58635 [4] | SC58635
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9677432
Reactome Reaction Reactome logo R-HSA-2309779
Other databases
CAS Registry No. 169590-42-5 (source: Scifinder)
ChEBI CHEBI:41423
ChEMBL Ligand CHEMBL118
DrugBank Ligand DB00482
DrugCentral Ligand 568
GtoPdb PubChem SID 178100241
PubChem CID 2662
RCSB PDB Ligand CEL
Search Google for chemical match using the InChIKey RZEKVGVHFLEQIL-UHFFFAOYSA-N
Search Google for chemicals with the same backbone RZEKVGVHFLEQIL
Search PubMed clinical trials celecoxib
Search PubMed titles celecoxib
Search PubMed titles/abstracts celecoxib
UniChem Compound Search for chemical match using the InChIKey RZEKVGVHFLEQIL-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey RZEKVGVHFLEQIL-UHFFFAOYSA-N
Wikipedia Celecoxib

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Tocris
Celecoxib (links to external site)
Cat. No. 3786