Celecoxib

Celecoxib
Clinical data
Pronunciation/sɛlɪˈkɒksɪb/ SEL-i-KOK-sib
Trade namesCelebrex, Onsenal, Elyxyb, Celebra, others
AHFS/Drugs.comMonograph
MedlinePlusa699022
License data
Pregnancy
category
Routes of
administration		By mouth
Drug classCyclooxygenase-2 (COX-2) inhibitor
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only) or S3[2][3]
  • BR: Class C1 (Other controlled substances)[4]
  • CA: ℞-only
  • NZ: Prescription only
  • UK: POM (Prescription only)[5]
  • US: ℞-only[6]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityUnknown[7]
Protein binding97% (mainly to serum albumin)[7]
MetabolismLiver (mainly CYP2C9)[7]
Elimination half-life7.8 hours; 11 hours (mild hepatic impairment); 13 hours (moderate-severe hepatic impairment)[7]
ExcretionFaeces (57%), urine (27%)[7]
Identifiers
IUPAC name
  • 4-[5-(4-Methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.211.644
Chemical and physical data
FormulaC17H14F3N3O2S
Molar mass381.37 g·mol−1
3D model (JSmol)
SMILES
  • c1cc(C)ccc1c2cc(C(F)(F)F)nn2c3ccc(cc3)S(=O)(=O)N
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) Y
  • Key:RZEKVGVHFLEQIL-UHFFFAOYSA-N Y
  (verify)

Celecoxib, sold under the brand name Celebrex among others, is a COX-2 inhibitor and nonsteroidal anti-inflammatory drug (NSAID).[8] 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.[8] It may also be used to decrease the risk of colorectal adenomas in people with familial adenomatous polyposis.[8] It is taken by mouth.[8] Benefits are typically seen within an hour.[8]

Common side effects include abdominal pain, nausea, and diarrhea.[8] Serious side effects may include heart attacks, strokes, gastrointestinal perforation, gastrointestinal bleeding, kidney failure, and anaphylaxis.[9][8] Use is not recommended in people at high risk for heart disease.[10][11] The risks are similar to other NSAIDs, such as ibuprofen and naproxen.[12] Use in the later part of pregnancy or during breastfeeding is not recommended.[8][1]

Celecoxib has demonstrated adjunctive benefits in major depression and efficacy in reducing polyp recurrence in familial adenomatous polyposis, while also being investigated for broader psychiatric, anticancer, and chemopreventive applications.

Celecoxib was patented in 1993 and came into medical use in 1999.[13] It is available as a generic medication.[14] In 2022, it was the 93rd most commonly prescribed medication in the United States, with more than 7 million prescriptions.[15][16]

  1. ^ a b "Celecoxib (Celebrex) Use During Pregnancy". Drugs.com. 4 May 2020. Archived from the original on 25 January 2021. Retrieved 5 May 2020.
  2. ^ "S3 celecoxib: expanding pharmacists' options for managing musculoskeletal pain". psa.org.au. April 2025. Retrieved 5 April 2025.
  3. ^ "Therapeutic Goods (Poisons Standard—February 2025) Instrument 2025". Federal Register of Legislation. February 2025. Retrieved 5 April 2025.
  4. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  5. ^ "Celebrex 100mg capsule - Summary of Product Characteristics (SmPC)". (emc). 13 January 2020. Archived from the original on 6 August 2020. Retrieved 5 May 2020.
  6. ^ Cite error: The named reference Celebrex FDA label was invoked but never defined (see the help page).
  7. ^ a b c d e McCormack PL (December 2011). "Celecoxib: a review of its use for symptomatic relief in the treatment of Osteoarthritis, Rheumatoid Arthritis, Psoriatic Arthritis and Ankylosing Spondylitis". Drugs. 71 (18): 2457–89. doi:10.2165/11208240-000000000-00000. PMID 22141388. S2CID 71357689.
  8. ^ a b c d e f g h "Celecoxib Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. 11 November 2019. Archived from the original on 20 May 2019. Retrieved 5 May 2020.
  9. ^ Cite error: The named reference Coxib2013 was invoked but never defined (see the help page).
  10. ^ Antman EM, Bennett JS, Daugherty A, Furberg C, Roberts H, Taubert KA (March 2007). "Use of nonsteroidal antiinflammatory drugs: an update for clinicians: a scientific statement from the American Heart Association". Circulation. 115 (12): 1634–42. doi:10.1161/circulationaha.106.181424. PMID 17325246.
  11. ^ "Should you still take Celebrex?". Consumer Reports. August 2009. Archived from the original on 18 December 2015. Retrieved 27 December 2015.
  12. ^ Stein R (25 April 2018). "FDA Panel Affirms Safety Of Painkiller Celebrex". NPR. Archived from the original on 20 May 2018. Retrieved 19 May 2018.
  13. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 522. ISBN 9783527607495. Archived from the original on 27 April 2021. Retrieved 13 October 2020.
  14. ^ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 1097–1098. ISBN 9780857113382.
  15. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  16. ^ "Celecoxib Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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