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].
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: celecoxib

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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)
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 EMA-endorsed marketing authorisation was withdrawn in 2009.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.