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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-10-17 08:34:38 UTC
Update Date2022-03-07 02:49:25 UTC
HMDB IDHMDB0005014
Secondary Accession Numbers
  • HMDB05014
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
Data?1582752340
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 Weight381.372
Monoisotopic Molecular Weight381.075882012
IUPAC Name4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide
Traditional 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
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
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point101.7 - 103.9 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM186.430932474
[M+H]+Not Available186.121http://allccs.zhulab.cn/database/detail?ID=AllCCS00001044
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+184.38430932474
DeepCCS[M-H]-182.02630932474
DeepCCS[M-2H]-216.29530932474
DeepCCS[M+Na]+191.46630932474
AllCCS[M+H]+185.732859911
AllCCS[M+H-H2O]+182.732859911
AllCCS[M+NH4]+188.532859911
AllCCS[M+Na]+189.332859911
AllCCS[M-H]-178.732859911
AllCCS[M+Na-2H]-177.832859911
AllCCS[M+HCOO]-177.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CelecoxibCC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F4575.6Standard polar33892256
CelecoxibCC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F2882.8Standard non polar33892256
CelecoxibCC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F2842.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Celecoxib,1TMS,isomer #1CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N[Si](C)(C)C)C=C2)C=C12895.1Semi standard non polar33892256
Celecoxib,1TMS,isomer #1CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N[Si](C)(C)C)C=C2)C=C12886.6Standard non polar33892256
Celecoxib,1TMS,isomer #1CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N[Si](C)(C)C)C=C2)C=C13504.4Standard polar33892256
Celecoxib,2TMS,isomer #1CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C12871.0Semi standard non polar33892256
Celecoxib,2TMS,isomer #1CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C13036.8Standard non polar33892256
Celecoxib,2TMS,isomer #1CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C13438.5Standard polar33892256
Celecoxib,1TBDMS,isomer #1CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)C=C2)C=C13135.6Semi standard non polar33892256
Celecoxib,1TBDMS,isomer #1CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)C=C2)C=C13122.7Standard non polar33892256
Celecoxib,1TBDMS,isomer #1CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)C=C2)C=C13498.7Standard polar33892256
Celecoxib,2TBDMS,isomer #1CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C13378.8Semi standard non polar33892256
Celecoxib,2TBDMS,isomer #1CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C13470.6Standard non polar33892256
Celecoxib,2TBDMS,isomer #1CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C13470.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Celecoxib GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uy0-0729000000-75ddea9acd30a029b25b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Celecoxib GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Celecoxib GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib LC-ESI-QFT , negative-QTOFsplash10-001i-0029000000-1a5ed66ff895eeb127ce2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib 75V, Negative-QTOFsplash10-014i-9100000000-9a8cd0b75d276f1086512021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib 90V, Negative-QTOFsplash10-02vi-9100000000-3b8e53549d02c7db5cba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib 60V, Negative-QTOFsplash10-014i-9220000000-e1d41283ce6235c1de0d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib 45V, Negative-QTOFsplash10-016r-7292000000-0c298e1f9b51823232c72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib 20V, Negative-QTOFsplash10-001i-0009000000-57c7836793a5363fda3d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib 30V, Negative-QTOFsplash10-017j-0198000000-927a7c09840b934e4cea2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib 10V, Negative-QTOFsplash10-001i-0009000000-e3bce1b4f36e339f9f392021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib 15V, Negative-QTOFsplash10-001i-0009000000-72b8641321f8f9f0f2b32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib 40V, Negative-QTOFsplash10-004i-0490000000-0b6fde7d96dea087de342021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib 35V, Negative-QTOFsplash10-001i-0029000000-79525e24a78b178217882021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib LC-ESI-qTof , Positive-QTOFsplash10-0aou-3960000000-2bd7d8539498dde5c2f52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib , positive-QTOFsplash10-001i-0129000000-a967b7f9e88a461e3db42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib , positive-QTOFsplash10-01q9-2598000000-f71f4f9eb7c83ddf79f42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib LC-ESI-QFT , positive-QTOFsplash10-001i-0029000000-13ff69b3abd31dde6bae2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib 10V, Positive-QTOFsplash10-001i-0009000000-41eaecd214cbc50e645e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib 20V, Positive-QTOFsplash10-001i-0009000000-f2376e3bc87d5951988c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib 40V, Positive-QTOFsplash10-0gx0-0059000000-9e48db23da1b4b859e682021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib 30V, Positive-QTOFsplash10-001i-0009000000-25406fbf853a86a41e2f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib 50V, Positive-QTOFsplash10-001i-0293000000-c8b94b6bd1da23395b782021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib 45V, Positive-QTOFsplash10-016r-8292000000-c913cc6bc3b2c8e470be2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib 40V, Positive-QTOFsplash10-004i-0490000000-5319cfe9d2a6f759b0f52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib 30V, Positive-QTOFsplash10-001i-0009000000-3cc12dc7778c26ffd2e32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Celecoxib 35V, Positive-QTOFsplash10-001i-0019000000-0e58c5a12f13da2c21172021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Celecoxib 10V, Negative-QTOFsplash10-001i-0009000000-9d1a9c471dc123cee7352016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0257 +/- 1.33 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00482
Phenol Explorer Compound IDNot Available
FooDB IDFDB023586
KNApSAcK IDNot Available
Chemspider ID2562
KEGG Compound IDC07589
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCelecoxib
METLIN IDNot Available
PubChem Compound2662
PDB IDNot Available
ChEBI ID41423
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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