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Record Information
Version1.0
Creation Date2014-09-11 05:15:54 UTC
Update Date2016-11-09 01:09:12 UTC
Accession NumberCHEM003728
Identification
Common NameCelecoxib
ClassSmall Molecule
DescriptionCelecoxib is a non-steroidal anti-inflammatory drug (NSAID) used in the treatment of osteoarthritis, rheumatoid arthritis, acute pain, painful menstruation and menstrual symptoms, and to reduce numbers of colon and rectum polyps in patients with familial adenomatous polyposis. It is marketed by Pfizer under the brand name Celebrex. In some countries, it is branded Celebra. Celecoxib is available by prescription in capsule form.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Drug
  • Food Toxin
  • Metabolite
  • Organic Compound
  • Organofluoride
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
CelebrexChEBI
CelecoxibumChEBI
p-(5-p-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulfonamideChEBI
OnsenalKegg
p-(5-p-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulphonamideGenerator
CelocoxibHMDB
4-(5-(4-Methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamideHMDB
Chemical FormulaC17H14F3N3O2S
Average Molecular Mass381.372 g/mol
Monoisotopic Mass381.076 g/mol
CAS Registry Number169590-42-5
IUPAC Name4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide
Traditional Namecelecoxib
SMILESCC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F
InChI IdentifierInChI=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 KeyRZEKVGVHFLEQIL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassPyrazoles
Direct ParentPhenylpyrazoles
Alternative Parents
Substituents
  • Phenylpyrazole
  • Benzenesulfonamide
  • Benzenesulfonyl group
  • Toluene
  • Monocyclic benzene moiety
  • Organosulfonic acid amide
  • Benzenoid
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Heteroaromatic compound
  • Azacycle
  • Organic oxide
  • Alkyl halide
  • Alkyl fluoride
  • Organopnictogen compound
  • Organosulfur compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point158°C
Boiling PointNot Available
SolubilityVery low water solubility (3.3 mg/L)
Predicted Properties
PropertyValueSource
Water Solubility0.005 g/LALOGPS
logP3.99ALOGPS
logP4.01ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)10.7ChemAxon
pKa (Strongest Basic)-0.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area77.98 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity92.23 m³·mol⁻¹ChemAxon
Polarizability35.2 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0uy0-0729000000-75ddea9acd30a029b25bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0aou-3960000000-2bd7d8539498dde5c2f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-001i-0029000000-1a5ed66ff895eeb127ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0129000000-a967b7f9e88a461e3db4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01q9-2598000000-f71f4f9eb7c83ddf79f4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-0029000000-13ff69b3abd31dde6baeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-23d25f88a0e277e47c54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0009000000-a933645e1cf7fb8edf4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-3289000000-7c03de47cb9bd124fa0cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-9d1a9c471dc123cee735View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-bdb3f0787c9e831e7530View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9125000000-ad5803f68fece8f76b2aView in MoNA
Toxicity Profile
Route of ExposureWell 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%.
Mechanism of ToxicityThe 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.
MetabolismHepatic. 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.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor 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
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include breathing difficulties, coma, drowsiness, gastrointestinal bleeding, high blood pressure, kidney failure, nausea, sluggishness, stomach pain, and vomiting.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00482
HMDB IDHMDB0005014
FooDB IDFDB023586
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCelecoxib
Chemspider ID2562
ChEBI ID41423
PubChem Compound ID2662
Kegg Compound IDC07589
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

DrugSyn.org

MSDSLink
General References
1. Talley, John J.; Penning, Thomas D.; Collins, Paul W.; Rogier, Donald J., Jr.; Malecha, James W.; Miyashiro, Julie M.; Bertenshaw, Stephen R.; Khanna, Ish K.; Granets, Matthew J.; et al. Preparation of pyrazolylbenzenesulfonamides as antiinflammatories. PCT Int. Appl. (1995), 254 pp. CODEN: PIXXD2 WO 9515316 A1 19950608 CAN 123:340112 AN 1995:931246
2. Talley, John J.; Penning, Thomas D.; Collins, Paul W.; Rogier, Donald J., Jr.; Malecha, James W.; Miyashiro, Julie M.; Bertenshaw, Stephen R.; Khanna, Ish K.; Granets, Matthew J.; et al. Preparation of pyrazolylbenzenesulfonamides as antiinflammatories. PCT Int. Appl. (1995), 254 pp. CODEN: PIXXD2 WO 9515316 A1 19950608 CAN 123:340112 AN 1995:931246
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17983259
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18405470
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19137124
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19203891
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21955617
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22141388
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22419293
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22971036
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23296687
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23506230
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217