Editing Celecoxib (section)

{{Short description|Nonsteroidal anti-inflammatory medication}}
{{Use dmy dates|date=February 2024}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Infobox drug
| Watchedfields = changed
| verifiedrevid = 458612013
| image = Celecoxib.svg
| image_class = skin-invert-image
| width = 220
| alt = Skeletal formula of celecoxib
| image2 = Celecoxib-3D-spacefill.png
| image_class2 = bg-transparent
| width2 = 
| alt2 = Space-filling model of the celecoxib molecule
| caption =

<!-- Clinical data -->
| pronounce = {{IPAc-en|s|ɛ|l|ɪ|ˈ|k|ɒ|k|s|ɪ|b}} {{respell|SEL|i|KOK|sib}}
| tradename = Celebrex, Onsenal, Elyxyb, Celebra, others
| Drugs.com = {{drugs.com|monograph|celecoxib}}
| MedlinePlus = a699022
| DailyMedID = Celecoxib
| pregnancy_AU = B3
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Celecoxib (Celebrex) Use During Pregnancy | website=Drugs.com | date=4 May 2020 | url=https://www.drugs.com/pregnancy/celecoxib.html | access-date=5 May 2020 | archive-date=25 January 2021 | archive-url=https://web.archive.org/web/20210125072333/https://www.drugs.com/pregnancy/celecoxib.html | url-status=live }}</ref>
| pregnancy_category= 
| routes_of_administration = [[Oral administration|By mouth]]
| class = [[COX-2 inhibitor|Cyclooxygenase-2 (COX-2) inhibitor]]
| ATC_prefix = L01
| ATC_suffix = XX33
| ATC_supplemental = {{ATC|M01|AH01}}

<!-- Legal status -->
| legal_AU = S4
| legal_AU_comment = or S3<ref name=psa>{{cite web | title=S3 celecoxib: expanding pharmacists' options for managing musculoskeletal pain | website=psa.org.au | date=April 2025 | url=https://my.psa.org.au/s/training-plan/a11RF000004PtWrYAK/s3-celecoxib-expanding-pharmacists-options-for-managing-musculoskeletal-pain | access-date=5 April 2025 }}</ref><ref>{{cite web | title=Therapeutic Goods (Poisons Standard—February 2025) Instrument 2025 | website=Federal Register of Legislation | date=February 2025 | url=https://www.legislation.gov.au/F2025L00049/latest/text | access-date=5 April 2025 }}</ref>
| legal_BR = C1
| legal_BR_comment = <ref>{{cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=31 March 2023 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=3 August 2023 |access-date=16 August 2023 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=4 April 2023}}</ref>
| legal_CA = Rx-only
| legal_CA_comment = 
| legal_DE = <!-- Anlage I, II, III or Unscheduled-->
| legal_DE_comment = 
| legal_NZ = Prescription only
| legal_NZ_comment =
| legal_UK = POM
| legal_UK_comment = <ref>{{cite web | title=Celebrex 100mg capsule - Summary of Product Characteristics (SmPC) | website=(emc) | date=13 January 2020 | url=https://www.medicines.org.uk/emc/product/5533/smpc | access-date=5 May 2020 | archive-date=6 August 2020 | archive-url=https://web.archive.org/web/20200806222736/https://www.medicines.org.uk/emc/product/5533/smpc | url-status=live }}</ref>
| legal_US = Rx-only
| legal_US_comment = <ref name="Celebrex FDA label" />
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->
| legal_UN_comment = 
| legal_status = Rx-only

<!-- Pharmacokinetic data -->
| bioavailability = Unknown<ref name=drugs>{{cite journal | vauthors = McCormack PL | title = Celecoxib: a review of its use for symptomatic relief in the treatment of Osteoarthritis, Rheumatoid Arthritis, Psoriatic Arthritis and Ankylosing Spondylitis | journal = Drugs | volume = 71 | issue = 18 | pages = 2457–89 | date = December 2011 | pmid = 22141388 | doi = 10.2165/11208240-000000000-00000 | s2cid = 71357689 }}</ref>
| protein_bound = 97% (mainly to [[serum albumin]])<ref name = drugs/>
| metabolism = Liver (mainly [[CYP2C9]])<ref name = drugs/>
| metabolites = 
| onset = 
| elimination_half-life = 7.8 hours; 11 hours (mild hepatic impairment); 13 hours (moderate-severe hepatic impairment)<ref name = drugs/>
| duration_of_action = 
| excretion = Faeces (57%), urine (27%)<ref name = drugs/>

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 169590-42-5
| CAS_supplemental = 
| PubChem = 2662
| IUPHAR_ligand = 2892
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00482
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2562
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = JCX84Q7J1L
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00567
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 41423
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 118
| NIAID_ChemDB = 
| PDB_ligand = CEL
| synonyms =

<!-- Chemical and physical data -->
| IUPAC_name = 4-[5-(4-Methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
| C=17 | H=14 | F=3 | N=3 | O=2 | S=1
| SMILES = c1cc(C)ccc1c2cc(C(F)(F)F)nn2c3ccc(cc3)S(=O)(=O)N
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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)
| StdInChI_comment = 
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RZEKVGVHFLEQIL-UHFFFAOYSA-N
| density = 
| density_notes = 
| melting_point = 
| melting_high = 
| melting_notes = 
| boiling_point = 
| boiling_notes = 
| solubility = 
| sol_units = 
| specific_rotation = 
}}

<!-- Definition and uses -->
'''Celecoxib''', sold under the brand name '''Celebrex''' among others, is a [[COX-2 inhibitor]] and [[nonsteroidal anti-inflammatory drug]] (NSAID).<ref name=AHFS2019>{{cite web |title=Celecoxib Monograph for Professionals |url=https://www.drugs.com/monograph/celecoxib.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |date=11 November 2019 |access-date=5 May 2020 |archive-date=20 May 2019 |archive-url=https://web.archive.org/web/20190520124313/https://www.drugs.com/monograph/celecoxib.html |url-status=live }}</ref> 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]].<ref name=AHFS2019/> It may also be used to decrease the risk of [[colorectal adenoma]]s in people with [[familial adenomatous polyposis]].<ref name=AHFS2019/> It is taken [[Oral administration|by mouth]].<ref name=AHFS2019/> Benefits are typically seen within an hour.<ref name=AHFS2019/>

<!-- Side effects and mechanism -->
Common side effects include [[abdominal pain]], nausea, and [[diarrhea]].<ref name=AHFS2019/> Serious side effects may include [[myocardial infarction|heart attacks]], [[stroke]]s, [[gastrointestinal perforation]], [[gastrointestinal bleeding]], [[kidney failure]], and [[anaphylaxis]].<ref name=Coxib2013/><ref name=AHFS2019/> Use is not recommended in people at high risk for heart disease.<ref name=AHA2007>{{cite journal | vauthors = Antman EM, Bennett JS, Daugherty A, Furberg C, Roberts H, Taubert KA | title = Use of nonsteroidal antiinflammatory drugs: an update for clinicians: a scientific statement from the American Heart Association | journal = Circulation | volume = 115 | issue = 12 | pages = 1634–42 | date = March 2007 | pmid = 17325246 | doi = 10.1161/circulationaha.106.181424 | doi-access = free }}</ref><ref name=Consumer2012>{{cite web | url=http://www.consumerreports.org/cro/2012/05/should-you-still-take-celebrex/index.htm | title=Should you still take Celebrex? | work=[[Consumer Reports]] | date=August 2009 | access-date=27 December 2015 | archive-date=18 December 2015 | archive-url=https://web.archive.org/web/20151218111927/http://www.consumerreports.org/cro/2012/05/should-you-still-take-celebrex/index.htm | url-status=live }}</ref> The risks are similar to other NSAIDs, such as [[ibuprofen]] and [[naproxen]].<ref name=NPR2018>{{cite news| vauthors = Stein R |title=FDA Panel Affirms Safety Of Painkiller Celebrex|url=https://www.npr.org/sections/health-shots/2018/04/25/605226604/fda-panel-affirms-safety-of-painkiller-celebrex|access-date=19 May 2018|publisher=[[NPR]]|date=25 April 2018|archive-date=20 May 2018|archive-url=https://web.archive.org/web/20180520123906/https://www.npr.org/sections/health-shots/2018/04/25/605226604/fda-panel-affirms-safety-of-painkiller-celebrex|url-status=live}}</ref> Use in the later part of [[pregnancy]] or during [[breastfeeding]] is not recommended.<ref name=AHFS2019/><ref name="Drugs.com pregnancy" />

Celecoxib has demonstrated [[Combination therapy|adjunctive]] benefits in [[Major depressive disorder|major depression]] and efficacy in reducing polyp recurrence in [[familial adenomatous polyposis]], while also being investigated for broader psychiatric, anticancer, and chemopreventive applications.

<!-- History, society, and culture -->
Celecoxib was patented in 1993 and came into medical use in 1999.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=522 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA522 |access-date=13 October 2020 |archive-date=27 April 2021 |archive-url=https://web.archive.org/web/20210427093939/https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA522 |url-status=live }}</ref> It is available as a [[generic medication]].<ref name=BNF76>{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=1097–1098|edition=76}}</ref> In 2022, it was the 93rd most commonly prescribed medication in the United States, with more than 7{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Celecoxib Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Celecoxib | access-date = 30 August 2024 }}</ref>