Human Metabolome Database Version 3.5

Showing metabocard for Celecoxib (HMDB05014)

Record Information
Version 3.5
Creation Date 2006-10-17 02:34:38 -0600
Update Date 2013-02-08 17:13:46 -0700
HMDB ID HMDB05014
Secondary Accession Numbers None
Metabolite Identification
Common Name Celecoxib
Description Celecoxib (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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Celebrex
  2. Celecoxib
  3. Celocoxib
Chemical Formula C17H14F3N3O2S
Average Molecular Weight 381.372
Monoisotopic Molecular Weight 381.075882012
IUPAC Name 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide
Traditional IUPAC Name celecoxib
CAS Registry Number 169590-42-5
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 Key RZEKVGVHFLEQIL-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Phenylpyrazoles
Sub Class N/A
Other Descriptors
  • Aminobenzenesulfonamides
  • Aromatic Heteropolycyclic Compounds
  • organofluorine compound(ChEBI)
  • pyrazoles(ChEBI)
  • sulfonamide(ChEBI)
Substituents
  • Organic Halide
  • Organofluoride
  • Pyrazole
  • Sulfonamide
  • Sulfonyl
  • Toluene
Direct Parent Phenylpyrazoles
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 101.7 - 103.9 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.005 g/L ALOGPS
LogP 3.99 ALOGPS
LogP 4.01 ChemAxon
LogS -4.88 ALOGPS
pKa (strongest acidic) 10.7 ChemAxon
pKa (strongest basic) -0.42 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 77.98 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 92.23 ChemAxon
Polarizability 35.18 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.0257 +/- 1.33 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023586
KNApSAcK ID Not Available
Chemspider ID 2562 Link_out
KEGG Compound ID C07589 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Celecoxib Link_out
NuGOwiki Link HMDB05014 Link_out
Metagene Link HMDB05014 Link_out
METLIN ID Not Available
PubChem Compound 2662 Link_out
PDB ID CEL Link_out
ChEBI ID 41423 Link_out
References
Synthesis Reference 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
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available

Enzymes
Name: Prostaglandin G/H synthase 2
Reactions: Not Available
Gene Name: PTGS2
Uniprot ID: P35354 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C9
Reactions: Not Available
Gene Name: CYP2C9
Uniprot ID: P11712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3-phosphoinositide-dependent protein kinase 1
Reactions: Not Available
Gene Name: PDPK1
Uniprot ID: O15530 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: P10635 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA