1.0 2014-09-11 05:15:54 UTC 2026-08-19 18:34:38 UTC T3D4771 Celecoxib SmallMolecule Celecoxib is an exogenous organic compound with the formula C17H14F3N3O2S and an average molecular weight of 381.37 g/mol. It exists as a solid at room temperature. Celecoxib belongs to the pyrazoles, a subclass of azoles within the organic compounds. The compound acts as an inhibitor of Nuclear receptor subfamily 1 group I member 2 (NR1I2) and targets the Vitamin D3 receptor (VDR), Cytochrome P450 2C9 (CYP2C9), and Estrogen receptor beta (ESR2), among eight other proteins. It is used in the treatment of pain (PMC12684957), fever (PMC7470770, PMC8332605), ovarian cancer (PMC8072532), arthritis (PMC11226812, PMC13029672, PMC8933701), and inflammation (PMC8332605). Additionally, it has therapeutic effects on inflammation (PMC12684957), pain (PMC12684957), fatigue (PMC5013212), and skin cancer (PMC2935905). However, the compound is associated with bleeding (PMC11226812) and an increase in stroke (PMC11226812). Celecoxib is found in or released from 25 recorded sources, including healthcare, pharmaceuticals and veterinary products such as analgesics, antiinflammatory and antirheumatic products, antineoplastic agents, and calcium channel blockers. Other sources include indoor air, food processing and cookware (preparation of wort, food preservation, and fermentation processes for beer), household cleaning and consumer products (bleaching agents, perfumes within detergents and soaps, and smoking requisites), and electrical and electronic equipment (conductors, electrodes, and hybrid capacitors). Recorded exposure routes include oral, topical, and inhalation. Drug Food Toxin Synthetic Toxin Organic Compound Organofluoride Amide Drug Food Toxin Metabolite Synthetic Compound Human Neurotoxin 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide Articox Articoxib Artiflex Artilog Artix Artrixib Blockten Caditar Cefinix Celact Celebra Celebrex Celecoxibum Celocoxib Onsenal P-(5-P-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulfonamide Valdyne C17H14F3N3O2S 381.372 381.075882012 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide celecoxib 169590-42-5 CC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F 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) RZEKVGVHFLEQIL-UHFFFAOYSA-N Organic compounds Organoheterocyclic compounds Azoles Pyrazoles Phenylpyrazoles Alkyl fluorides Aminosulfonyl compounds Azacyclic compounds Benzenesulfonamides Benzenesulfonyl compounds Heteroaromatic compounds Hydrocarbon derivatives Organic oxides Organofluorides Organonitrogen compounds Organopnictogen compounds Organosulfonamides Toluenes Alkyl fluoride Alkyl halide Aminosulfonyl compound Aromatic heteromonocyclic compound Azacycle Benzenesulfonamide Benzenesulfonyl group Benzenoid Heteroaromatic compound Hydrocarbon derivative Monocyclic benzene moiety Organic nitrogen compound Organic oxide Organic oxygen compound Organic sulfonic acid or derivatives Organofluoride Organohalogen compound Organonitrogen compound Organopnictogen compound Organosulfonic acid amide Organosulfonic acid or derivatives Organosulfur compound Phenylpyrazole Sulfonyl Toluene Aromatic heteromonocyclic compounds organofluorine compound pyrazoles sulfonamide Detected and Not Quantified Exogenous Membrane Celecoxib metabolism Pathway SMP0000096 Celecoxib metabolism Pathway SMP0000644 Celecoxib Action Pathway (New) SMP0126384 Celecoxib Drug Metabolism Action Pathway SMP0142936 Solid White powder. melting_point 158°C solubility Very low water solubility (3.3 mg/L) logp 3.9 logp 3.99 ALOGPS logs -4.88 ALOGPS solubility 5.03e-03 g/l ALOGPS logp 4.01 ChemAxon pka_strongest_acidic 10.7 ChemAxon pka_strongest_basic -0.42 ChemAxon iupac 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide ChemAxon average_mass 381.372 ChemAxon mono_mass 381.075882012 ChemAxon smiles CC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F ChemAxon formula C17H14F3N3O2S ChemAxon 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) ChemAxon inchikey RZEKVGVHFLEQIL-UHFFFAOYSA-N ChemAxon polar_surface_area 77.98 ChemAxon refractivity 92.23 ChemAxon polarizability 35.2 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Well absorbed in the gastrointestinal tract. When a single dose of 200 mg is given to healthy subjects, peak plasma levels occur 3 hours after an oral dose. The peak plasma level is 705 ng/mL. Absolute bioavailability studies have not been conducted. When multiple doses are given, steady-state is reached on or before Day 5. When taken with a high fat meal, peak plasma levels are delayed for about 1 to 2 hours with an increase in total absorption (AUC) of 10% to 20%. The mechanism of action of celecoxib is believed to be due to inhibition of prostaglandin synthesis. Unlike most NSAIDs, which inhibit both types of cyclooxygenases (COX-1 and COX-2), celecoxib is a selective noncompetitive inhibitor of cyclooxygenase-2 (COX-2) enzyme. It binds with its polar sulfonamide side chain to a hydrophilic side pocket region close to the active COX-2 binding site. Both COX-1 and COX-2 catalyze the conversion of arachidonic acid to prostaglandin (PG) H2, the precursor of PGs and thromboxane. Hepatic. Celecoxib metabolism is primarily mediated via cytochrome P450 2C9. Three metabolites, a primary alcohol, the corresponding carboxylic acid and its glucuronide conjugate, have been identified in human plasma. CYP3A4 is also involved in the hydroxylation of celecoxib but to a lesser extent. These metabolites are inactive as COX-1 or COX-2 inhibitors. Route of Elimination: Celecoxib is eliminated predominantly by hepatic metabolism with little (<3%) unchanged drug recovered in the urine and feces. 57% of the oral dose is excreted in the feces and 27% is excreted into the urine. The primary metabolite in urine and feces was the carboxylic acid metabolite (73%). The amount of glucuronide in the urine is low. Half Life: The effective half-life is approximately 11 hours when a single 200 mg dose is given to healthy subjects. Terminal half-life is generally variable because of the low solubility of the drug thus prolonging absorption. No indication of carcinogenicity to humans (not listed by IARC). For relief and management of osteoarthritis (OA), rheumatoid arthritis (RA), juvenile rheumatoid arthritis (JRA), ankylosing spondylitis, acute pain, primary dysmenorrhea and oral adjunct to usual care for patients with familial adenomatous polyposis #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7226bbf798> Symptoms of overdose include breathing difficulties, coma, drowsiness, gastrointestinal bleeding, high blood pressure, kidney failure, nausea, sluggishness, stomach pain, and vomiting. DB00482 HMDB05014 2662 CHEMBL118 2562 C07589 3520 CEL Celecoxib 15208519 10979111 15713944 16777855 16943400 12392591 FDA label BE0000262 BE0001193 BE0000792 AC50 3.93 uM OT_ER_ERaERb_0480 Odyssey Thera AC50 9.64 uM OT_ER_ERbERb_0480 Odyssey Thera BE0000956 AC50 4.23 uM ATG_PXRE_CIS Attagene BE0002793 AC50 4.87 uM NVS_ADME_hCYP2C9 Novascreen BE0000123 AC50 6.25 uM Tox21_ERa_LUC_BG1_Agonist Tox21/NCGC BE0000779 AC50 7.34 uM ATG_VDRE_CIS Attagene BE0000322 BE0003625 BE0010959 BE0000914 BE0003462