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.
OverviewAI-generated
Celecoxib is a chemical compound with the formula C₁₇H₁₄F₃N₃O₂S. Its IUPAC name is 4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide. The substance has a mass of 381.076 and a weight of 381.4. It carries a stylized name of CeleBREX.
The compound has a defined daily dose of 0.2. Its chemical properties include an xlogp of 3.4, a topological polar surface area of 86.4, and a charge of 0. It features one hydrogen bond donor and seven hydrogen bond acceptors.
Celecoxib is referenced by 840 other encyclopedia articles. A search for celecoxib in PubMed yields a count of 9052.
Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
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
- Subclass of
- chemical compound
- Mass
- 381.076
- Has use
- medication
Show 11 more facts
- chemical formula
- C₁₇H₁₄F₃N₃O₂S
- medical condition treated
- spondylitis
- 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
- subject has role
- COX-2 inhibitor
- defined daily dose
- 0.2
- physically interacts with
- Prostaglandin-endoperoxide synthase 2
- stylized name
- CeleBREX
- legal status (medicine)
- boxed warning
- significant drug interaction
- tacrolimus
Sources (7)
via Wikidata · CC0
~23 min read
Encyclopedic overview
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.
Excerpted from Wikipedia’s “celecoxib” article, available under the CC BY-SA 4.0 licence.