Celecoxib

Celecoxib
Clinical data
Pronunciation	/sɛlɪˈkɒksɪb/ SEL-i-KOK-sib
Trade names	Celebrex, Onsenal, Elyxyb, others
AHFS/Drugs.com	Monograph
MedlinePlus	a699022
License data	US DailyMed: Celecoxib;
Pregnancy; category	AU: B3;
Routes of; administration	By mouth
Drug class	Cyclooxygenase-2 (COX-2) inhibitor
ATC code	L01XX33 (WHO) M01AH01 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); CA: ℞-only; NZ: Prescription only; UK: POM (Prescription only); US: WARNINGRx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Unknown
Protein binding	97% (mainly to serum albumin)
Metabolism	Liver (mainly CYP2C9)
Elimination half-life	7.8 hours; 11 hours (mild hepatic impairment); 13 hours (moderate-severe hepatic impairment)
Excretion	Faeces (57%), urine (27%)
Identifiers
	IUPAC name 4-[5-(4-Methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide;
CAS Number	169590-42-5 ;
PubChem CID	2662;
IUPHAR/BPS	2892;
DrugBank	DB00482 ;
ChemSpider	2562 ;
UNII	JCX84Q7J1L;
KEGG	D00567 ;
ChEBI	CHEBI:41423 ;
ChEMBL	ChEMBL118 ;
PDB ligand	CEL (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID0022777 ;
ECHA InfoCard	100.211.644
Chemical and physical data
Formula	C17H14F3N3O2S
Molar mass	381.37 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) ; Key:RZEKVGVHFLEQIL-UHFFFAOYSA-N ;
	(verify)

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.

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

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