Celecoxib
Celecoxib is an oral COX-2 selective non-steroidal anti-inflammatory drug used in adults for osteoarthritis, rheumatoid arthritis, ankylosing spondylitis, acute pain and primary dysmenorrhoea, with reduced upper gastrointestinal toxicity.
- Chemical formula
- C17H14F3N3O2S
- CAS number
- 169590-42-5
- ATC code
- M01AH01
- Molecular weight
- 381.37 g/mol
- Drug class
- COX-2 selective NSAID
- Also known as
- SC-58635, Celecoxib
What is it?
Celecoxib is the first selective inhibitor of cyclooxygenase-2 (COX-2) approved for clinical use, introduced in 1998. It is supplied as oral capsules at multiple strengths and is dispensed only on prescription. Celecoxib is widely used in chronic inflammatory conditions when reduced upper gastrointestinal toxicity compared with traditional non-selective NSAIDs is desirable, and is part of the World Health Organization List of Essential Medicines.
Mechanism of action
Celecoxib selectively inhibits cyclooxygenase-2 (COX-2), the enzyme isoform induced at sites of inflammation, which produces the prostaglandins responsible for pain, fever and inflammation. Compared with non-selective NSAIDs, it has limited inhibition of COX-1 at therapeutic doses, which spares prostaglandins involved in gastric mucosal protection and platelet aggregation. The result is anti-inflammatory and analgesic activity with reduced upper gastrointestinal toxicity.
Pharmacokinetics
Celecoxib is well absorbed orally, with peak plasma concentrations reached after two to three hours. Plasma protein binding is approximately 97%. The drug is metabolised mainly by CYP2C9 to inactive metabolites and excreted in urine and faeces. The terminal half-life is approximately 11 hours, supporting once or twice-daily dosing. CYP2C9 poor metabolisers have higher exposure and require lower starting doses according to the prescribing information.
Indications
Celecoxib is approved in adults for the treatment of osteoarthritis, rheumatoid arthritis, ankylosing spondylitis, acute pain in adults and primary dysmenorrhoea. In some markets it is also approved in juvenile rheumatoid arthritis from age 2 with weight-based dosing. Celecoxib was previously indicated for familial adenomatous polyposis but this indication has been withdrawn in many regions. According to clinical guidelines, the lowest effective dose for the shortest necessary duration should be used.
Safety profile
Common adverse effects include gastrointestinal symptoms (less frequent than with traditional NSAIDs), peripheral oedema, hypertension and headache. Celecoxib carries class warnings on cardiovascular thrombotic events including myocardial infarction and stroke, particularly with long-term high-dose use, and on serious gastrointestinal events. Renal impairment, hyperkalaemia and hepatotoxicity have been reported. According to the prescribing information, contraindications include severe heart failure, recent CABG surgery and known sulphonamide hypersensitivity.
Products containing this ingredient
Frequently asked questions
How is celecoxib safer than ibuprofen for the stomach? ▾
Celecoxib selectively inhibits COX-2 and largely spares COX-1, which produces protective prostaglandins in the gastric mucosa. As a result, large randomised trials have shown a lower rate of upper gastrointestinal ulcers and bleeding compared with non-selective NSAIDs at equivalent anti-inflammatory doses. According to clinical guidelines, celecoxib is preferred when gastrointestinal risk is high, although the cardiovascular profile must also be considered.
Does celecoxib increase cardiovascular risk? ▾
All NSAIDs, including celecoxib, can increase the risk of thrombotic cardiovascular events such as myocardial infarction and stroke, particularly with high doses and prolonged use. Large comparative trials suggest that the cardiovascular risk of celecoxib at typical doses is similar to that of naproxen and ibuprofen. According to the prescribing information, the prescriber should weigh cardiovascular and gastrointestinal risks in each patient.
Why is sulphonamide allergy a concern with celecoxib? ▾
Celecoxib contains a sulphonamide group in its chemical structure. According to the prescribing information, it is contraindicated in patients with known hypersensitivity to sulphonamides because of the theoretical risk of cross-reactivity. The clinical relevance is debated, but caution is recommended, particularly in patients with severe prior reactions to sulphonamide antibiotics.
Should celecoxib be combined with low-dose aspirin? ▾
Celecoxib does not provide the same antiplatelet protection as low-dose aspirin used for cardiovascular prevention. In patients on low-dose aspirin who require an NSAID, the combination can be used when needed, but the gastrointestinal advantage of celecoxib over non-selective NSAIDs is reduced. According to clinical guidelines, gastric protection with a proton pump inhibitor may be considered, with the regimen tailored by the prescriber.
What are the main contraindications for celecoxib? ▾
Celecoxib is contraindicated in known hypersensitivity to celecoxib, sulphonamides or NSAIDs, in active peptic ulcer or gastrointestinal bleeding, in severe heart failure, in the perioperative period of coronary artery bypass graft surgery, in severe hepatic impairment and during the third trimester of pregnancy. Caution is required in renal impairment, hypertension and other cardiovascular risk factors. According to the prescribing information, the medical history must be reviewed by a clinician before any prescription.
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