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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View more information in the IUPHAR Pharmacology Education Project: celecoxib

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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
No information available.
Summary of Clinical Use Click here for help
Celecoxib is used to treat osteoarthritis, rheumatoid arthritis, acute pain, painful menstruation and menstrual symptoms. It is also used to reduce the number of colon and rectal polyps in patients with familial adenomatous polyposis. In May 2020, the FDA approved celecoxib (as an oral solution, Elyxyb®) as a treatment for adults suffering acute migraine with or without aura. EMA-endorsed marketing authorisation was withdrawn in 2009.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Celecoxib is a selective noncompetitive inhibitor of cyclooxygenase-2 (COX-2) and does not inhibit COX-1. Inhibition of COX-2 reduces synthesis of prostaglandin precursors from arachadonic acid.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03009019 Efficacy, Tolerability, and Safety of DFN-15 Phase 3 Interventional Dr. Reddy's Laboratories Limited
NCT03006276 Efficacy, Tolerability, and Safety Study of DFN-15 Phase 3 Interventional Dr. Reddy's Laboratories Limited Celecoxib was delivered as an oral solution (DFN-15) to overcome gastroinetstinal tolerability issues. DFN‐15 was found to be significantly more effective than placebo for the acute treatment of migraine. 3
NCT00001693 Phase I-II Multiple-Dose Safety and Efficacy Study of a Selective Inhibitor of Cyclooxygenase - 2 (SC-58635) in Hereditary Non-Polyposis Colorectal Cancer (HNPCC) Patients and Carriers Phase 1 Interventional National Institutes of Health Clinical Center (CC) Celecoxib has been evaluated for chemopreventive activity in patients with Lynch syndrome (LS; a.k.a. hereditary nonpolyposis colorectal cancer, HNPCC). NSAIDs are predicted to offer efficacy in this condition via a mechanism that modulates the immune activation that is observed in LS colorectal adenomas and tumours.