Structure via PubChem · Public domain (PubChem)
celecoxib
Sign in to saveAlso known as Celecox®, Onsenal®, Celocoxib, 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide, Celebrex, Celecoxibum, Célécoxib
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.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 458612013
- Drug.image
- Celecoxib.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 220
- Drug.alt
- Skeletal formula of celecoxib
- Drug.image2
- Celecoxib-3D-spacefill.png
- Drug.image_class2
- bg-transparent
- Drug.alt2
- Space-filling model of the celecoxib molecule
- Drug.tradename
- Celebrex, Onsenal, Elyxyb, Celebra, others
- Drug.MedlinePlus
- a699022
- Drug.DailyMedID
- Celecoxib
- Drug.pregnancy_AU
- B3
- Drug.routes_of_administration
- By mouth
- Drug.class
- Cyclooxygenase-2 (COX-2) inhibitor
- Drug.ATC_prefix
- L01
- Drug.ATC_suffix
- XX33
- Drug.legal_AU
- S4
via Wikipedia infobox
Chemical data
- Formula
- C17H14F3N3O2S
- Molecular weight
- 381.4 g/mol
- IUPAC name
- 4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
- SMILES
- CC1=CC=C(C=C1)C2=CC(=NN2C3=CC=C(C=C3)S(=O)(=O)N)C(F)(F)F
- InChIKey
- RZEKVGVHFLEQIL-UHFFFAOYSA-N
- XLogP
- 3.4
- Polar surface area
- 86.4 Ų
- H-bond donors
- 1
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Research
9,052 papersvia PubMed
Wikidata facts
- Mass
- 381.076
Show 6 more facts
- chemical formula
- C₁₇H₁₄F₃N₃O₂S
- Commons category
- Celecoxib
- canonical SMILES
- CC1=CC=C(C=C1)C2=CC(=NN2C3=CC=C(C=C3)S(=O)(=O)N)C(F)(F)F
- World Health Organisation international non-proprietary name
- celecoxib
- defined daily dose
- 0.2
- stylized name
- CeleBREX
Sources (7)
via Wikidata · CC0
~23 min read
Article
23 sectionsContents
- Medical uses
- Familial adenomatous polyposis
- Adverse effects
- Allergy
- Heart attack and stroke
- Drug interactions
- Mechanism of action
- Anti-inflammatory
- Anti-cancer
- Structure-activity relationship
- History
- Society and culture
- Fabricated efficacy studies
- Brand names
- Research
- Psychiatry
- Bipolar disorder
- Familial adenomatous polyposis
- Cancer prevention
- Cancer treatment
- References
- Further reading
- External links
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.