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Celecoxib information


Celecoxib
Skeletal formula of celecoxib
Space-filling model of the celecoxib molecule
Clinical data
Pronunciation/sɛlɪˈkɒksɪb/ SEL-i-KOK-sib
Trade namesCelebrex, Onsenal, Elyxyb, others
AHFS/Drugs.comMonograph
MedlinePlusa699022
License data
  • US DailyMed: Celecoxib
Pregnancy
category
  • AU: B3[1]
Routes of
administration
By mouth
Drug classCyclooxygenase-2 (COX-2) inhibitor
ATC code
  • L01XX33 (WHO) M01AH01 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[3]
  • CA: ℞-only
  • NZ: Prescription only
  • UK: POM (Prescription only)[4]
  • US: WARNING[2]Rx-only[5]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityUnknown[6]
Protein binding97% (mainly to serum albumin)[6]
MetabolismLiver (mainly CYP2C9)[6]
Elimination half-life7.8 hours; 11 hours (mild hepatic impairment); 13 hours (moderate-severe hepatic impairment)[6]
ExcretionFaeces (57%), urine (27%)[6]
Identifiers
IUPAC name
  • 4-[5-(4-Methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
CAS Number
  • 169590-42-5 checkY
PubChem CID
  • 2662
IUPHAR/BPS
  • 2892
DrugBank
  • DB00482 checkY
ChemSpider
  • 2562 checkY
UNII
  • JCX84Q7J1L
KEGG
  • D00567 checkY
ChEBI
  • CHEBI:41423 checkY
ChEMBL
  • ChEMBL118 checkY
PDB ligand
  • CEL (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID0022777 Edit this at Wikidata
ECHA InfoCard100.211.644 Edit this at Wikidata
Chemical and physical data
FormulaC17H14F3N3O2S
Molar mass381.37 g·mol−1
3D model (JSmol)
  • Interactive image
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) checkY
  • Key:RZEKVGVHFLEQIL-UHFFFAOYSA-N checkY
  (verify)

Celecoxib, sold under the brand name Celebrex among others, is a COX-2 inhibitor and nonsteroidal anti-inflammatory drug (NSAID).[7] 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.[7] It may also be used to decrease the risk of colorectal adenomas in people with familial adenomatous polyposis.[7] It is taken by mouth.[7] Benefits are typically seen within an hour.[7]

Common side effects include abdominal pain, nausea, and diarrhea.[7] Serious side effects may include heart attacks, strokes, gastrointestinal perforation, gastrointestinal bleeding, kidney failure, and anaphylaxis.[8][7] Use is not recommended in people at high risk for heart disease.[9][10] The risks are similar to other NSAIDs, such as ibuprofen and naproxen.[11] Use in the later part of pregnancy or during breastfeeding is not recommended.[7][1]

Celecoxib was patented in 1993 and came into medical use in 1999.[12] It is available as a generic medication.[13] In 2021, it was the 98th most commonly prescribed medication in the United States, with more than 7 million prescriptions.[14][15]

  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. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ 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.
  4. ^ "Celebrex 100mg capsule - Summary of Product Characteristics (SmPC)". (emc). 13 January 2020. Archived from the original on 6 August 2020. Retrieved 5 May 2020.
  5. ^ Cite error: The named reference Celebrex FDA label was invoked but never defined (see the help page).
  6. ^ 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.
  7. ^ 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.
  8. ^ Cite error: The named reference Coxib2013 was invoked but never defined (see the help page).
  9. ^ 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.
  10. ^ "Should you still take Celebrex?". Consumer Reports. August 2009. Archived from the original on 18 December 2015. Retrieved 27 December 2015.
  11. ^ 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.
  12. ^ 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.
  13. ^ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 1097–1098. ISBN 9780857113382.
  14. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  15. ^ "Celecoxib - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

and 21 Related for: Celecoxib information

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Celecoxib

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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...

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Cyclooxygenase

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gastrointestinal tract. Selectivity for COX-2 is the main feature of celecoxib, etoricoxib, and other members of this drug class. Because COX-2 is usually...

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Polmacoxib

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effects on urinary prostaglandin metabolites for both polmacoxib and celecoxib that suggest a similar cardiovascular risk profile. Further work by this...

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Rofecoxib

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includes several agents, degrees of COX-2 selectivity vary among them, with celecoxib (Celebrex) being the least COX-2 selective, and rofecoxib (Vioxx), valdecoxib...

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Chondroitin sulfate

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hydrochloride plus 200 mg of chondroitin sulfate three times daily, 200 mg of celecoxib daily, or placebo. Treatment was administered for 24 weeks. It showed...

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Discovery and development of cyclooxygenase 2 inhibitors

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COX-2 inhibitor, with Celebrex (celecoxib) launched in December 1998 and Vioxx (rofecoxib) launched in May 1999. Celecoxib and other COX-2 selective inhibitors...

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List of sulfonamides

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Simeprevir (NS3/4A protease inhibitor) Azabon Apricoxib (COX-2 inhibitor) Celecoxib (COX-2 inhibitor) Parecoxib (COX-2 inhibitor) Bosentan (endothelin receptor...

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Pyrazole

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adjacent nitrogen atoms. Notable drugs containing a pyrazole ring are celecoxib (celebrex) and the anabolic steroid stanozolol. Pyrazoles are synthesized...

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Monica Bertagnolli

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Molecular basis of colorectal cancer Cardiovascular risk associated with celecoxib in a clinical trial for colorectal adenoma prevention Dissecting the multicellular...

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Boxed warning

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boxed warning on their non-steroidal anti-inflammatory drug Celebrex (celecoxib) for cardiovascular and gastrointestinal risks. In 2005, the FDA issued...

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Antipyretic

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relatively selective for COX-2, including nimesulide, diclofenac and celecoxib. Phenazone-like drugs (pyrazolones), many of which have been largely phased...

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Nimesulide

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randomised, double-blind, clinical trial comparing the efficacy of nimesulide, celecoxib and rofecoxib in osteoarthritis of the knee". Drugs. 63 (Suppl 1): 37–46...

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Naproxen

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Libby P, Husni ME, et al. (December 2016). "Cardiovascular Safety of Celecoxib, Naproxen, or Ibuprofen for Arthritis". The New England Journal of Medicine...

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Paracetamol

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Phenazocine Phenoperidine Piminodine Piritramide Proheptazine Propiram Remifentanil Sufentanil Tapentadol Tilidine Tramadol (+celecoxib, +paracetamol) Viminol...

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Morphine

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Phenazocine Phenoperidine Piminodine Piritramide Proheptazine Propiram Remifentanil Sufentanil Tapentadol Tilidine Tramadol (+celecoxib, +paracetamol) Viminol...

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Heroin

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Phenazocine Phenoperidine Piminodine Piritramide Proheptazine Propiram Remifentanil Sufentanil Tapentadol Tilidine Tramadol (+celecoxib, +paracetamol) Viminol...

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Analgesic

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NSAIDs block both versions in general). These drugs (such as rofecoxib, celecoxib, and etoricoxib) are equally effective analgesics when compared with NSAIDs...

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Ketorolac

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assessed to be a relatively higher-risk NSAID when compared to aceclofenac, celecoxib, and ibuprofen. Like all NSAIDs, ketorolac can cause premature constriction...

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Salicylic acid

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Phenazocine Phenoperidine Piminodine Piritramide Proheptazine Propiram Remifentanil Sufentanil Tapentadol Tilidine Tramadol (+celecoxib, +paracetamol) Viminol...

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Ketamine

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Phenazocine Phenoperidine Piminodine Piritramide Proheptazine Propiram Remifentanil Sufentanil Tapentadol Tilidine Tramadol (+celecoxib, +paracetamol) Viminol...

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Etodolac

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somewhat COX-2 selective similar to celecoxib and other "COX-2 inhibitors." Unlike rofecoxib, both etodolac and celecoxib can fully inhibit COX-1 and are...

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