celecoxib (CHEBI:41423)

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ChEBI Name	celecoxib

ChEBI ID	CHEBI:41423

Definition	A member of the class of pyrazoles that is 1H-pyrazole which is substituted at positions 1, 3 and 5 by 4-sulfamoylphenyl, trifluoromethyl and p-tolyl groups, respectively. A cyclooxygenase-2 inhibitor, it is used in the treatment of arthritis.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:41418, CHEBI:3520

Supplier Information	ChemicalBook:CB14842247, ChemicalBook:CB54842250, ChemicalBook:CB74842249, ChemicalBook:CB44842248, ChemicalBook:CB93313564, ChemicalBook:CB91267649, ChemicalBook:CB7444681, eMolecules:901601, Selleckchem:Celecoxib, ZINC000002570895

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Wikipedia	License
Celecoxib, sold under the brand name Celebrex among others, is a COX-2 inhibitor and nonsteroidal anti-inflammatory drug (NSAID). It is used to treat the pain and inflammation in osteoarthritis, acute pain in adults, rheumatoid arthritis, psoriatic arthritis, ankylosing spondylitis, painful menstruation, and juvenile rheumatoid arthritis. It may also be used to decrease the risk of colorectal adenomas in people with familial adenomatous polyposis. It is taken by mouth. Benefits are typically seen within an hour. Common side effects include abdominal pain, nausea, and diarrhea. Serious side effects may include heart attacks, strokes, gastrointestinal perforation, gastrointestinal bleeding, kidney failure, and anaphylaxis. Use is not recommended in people at high risk for heart disease. The risks are similar to other NSAIDs, such as ibuprofen and naproxen. Use in the later part of pregnancy or during breastfeeding is not recommended. Celecoxib was patented in 1993 and came into medical use in 1999. It is available as a generic medication. In 2022, it was the 93rd most commonly prescribed medication in the United States, with more than 7 million prescriptions.
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Formula

C17H14F3N3O2S

Net Charge

Average Mass

381.370

Monoisotopic Mass

381.07588

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)

InChIKey

RZEKVGVHFLEQIL-UHFFFAOYSA-N

SMILES

CC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F

Roles Classification
Biological Role(s):	cyclooxygenase 2 inhibitor A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2. non-narcotic analgesic A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.

Application(s):	geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan. non-steroidal anti-inflammatory drug An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. non-narcotic analgesic A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.

ChEBI Ontology
Outgoing	celecoxib (CHEBI:41423) has role cyclooxygenase 2 inhibitor (CHEBI:50629) celecoxib (CHEBI:41423) has role geroprotector (CHEBI:176497) celecoxib (CHEBI:41423) has role non-narcotic analgesic (CHEBI:35481) celecoxib (CHEBI:41423) has role non-steroidal anti-inflammatory drug (CHEBI:35475) celecoxib (CHEBI:41423) is a organofluorine compound (CHEBI:37143) celecoxib (CHEBI:41423) is a pyrazoles (CHEBI:26410) celecoxib (CHEBI:41423) is a sulfonamide (CHEBI:35358) celecoxib (CHEBI:41423) is a toluenes (CHEBI:27024)

IUPAC Name

4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide

Synonyms	Sources
Celecoxib	KEGG COMPOUND
p-(5-p-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulfonamide	ChemIDplus

Brand Name	Source
Celebrex	KEGG DRUG

Last Modified

23 September 2021