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Record Information
Version3.6
Creation Date2006-10-17 08:34:38 UTC
Update Date2013-02-09 00:13:46 UTC
HMDB IDHMDB05014
Secondary Accession NumbersNone
Metabolite Identification
Common NameCelecoxib
DescriptionCelecoxib (INN) 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 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. Celecoxib is a highly selective COX-2 inhibitor and primarily inhibits this isoform of cyclooxygenase, whereas traditional NSAIDs inhibit both COX-1 and COX-2. Celecoxib is approximately 10-20 times more selective for COX-2 inhibition over COX-1. In theory, this specificity allows celecoxib and other COX-2 inhibitors to reduce inflammation (and pain) while minimizing gastrointestinal adverse drug reactions (e.g. stomach ulcers) that are common with non-selective NSAIDs. It also means that it has a reduced effect on platelet aggregation compared to traditional NSAIDs; Celecoxib is a highly selective COX-2 inhibitor and primarily inhibits this isoform of cyclooxygenase, whereas traditional NSAIDs inhibit both COX-1 and COX-2. Celecoxib is approximately 10-20 times more selective for COX-2 inhibition over COX-1. In theory, this specificity allows celecoxib and other COX-2 inhibitors to reduce inflammation (and pain) while minimizing gastrointestinal adverse drug reactions (e.g. stomach ulcers) that are common with non-selective NSAIDs. It also means that it has a reduced effect on platelet aggregation compared to traditional NSAIDs.
Structure
Thumb
Synonyms
  1. Celebrex
  2. Celecoxib
  3. Celocoxib
Chemical FormulaC17H14F3N3O2S
Average Molecular Weight381.372
Monoisotopic Molecular Weight381.075882012
IUPAC Name4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide
Traditional IUPAC Namecelecoxib
CAS Registry Number169590-42-5
SMILES
CC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F
InChI Identifier
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 KeyRZEKVGVHFLEQIL-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassPhenylpyrazoles
Sub ClassN/A
Other Descriptors
  • Aminobenzenesulfonamides
  • Aromatic Heteropolycyclic Compounds
  • organofluorine compound(ChEBI)
  • pyrazoles(ChEBI)
  • sulfonamide(ChEBI)
Substituents
  • Organic Halide
  • Organofluoride
  • Pyrazole
  • Sulfonamide
  • Sulfonyl
  • Toluene
Direct ParentPhenylpyrazoles
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point101.7 - 103.9 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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 area77.98ChemAxon
rotatable bond count4ChemAxon
refractivity92.23ChemAxon
polarizability35.18ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0257 +/- 1.33 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023586
KNApSAcK IDNot Available
Chemspider ID2562
KEGG Compound IDC07589
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCelecoxib
NuGOwiki LinkHMDB05014
Metagene LinkHMDB05014
METLIN IDNot Available
PubChem Compound2662
PDB IDCEL
ChEBI ID41423
References
Synthesis ReferenceTalley, 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
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
General function:
Involved in protein kinase activity
Specific function:
Phosphorylates and activates not only PKB/AKT, but also PKA, PKC-zeta, RPS6KA1 and RPS6KB1. May play a general role in signaling processes and in development. Isoform 3 is catalytically inactive
Gene Name:
PDPK1
Uniprot ID:
O15530
Molecular weight:
63151.3
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94