Celecoxib
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| Non-proprietary name | Celecoxib | ||||||||||||||||||
| other names |
4- [5- (4-methylphenyl) -3- (trifluoromethyl) pyrazol-1-yl] benzenesulfonamide |
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| Molecular formula | C 17 H 14 F 3 N 3 O 2 S | ||||||||||||||||||
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| Drug class |
COX-2 inhibitors , antineoplastic agents |
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| Molar mass | 381.37 g · mol -1 | ||||||||||||||||||
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
Celecoxib is a drug selected from the group of selective COX-2 inhibitor , in the treatment of degenerative joint diseases , rheumatoid arthritis and ankylosing spondylitis is used. It works against pain, inflammation and fever.
It was developed in the 1990s at Monsanto / Searle (later taken over by Pfizer) by Philip Needleman . Compared to other non-opioid analgesics, selective COX-2 inhibitors are significantly more expensive and always require a prescription.
Clinical information
Application areas (indications)
Celecoxib is approved for the treatment of degenerative joint diseases ( osteoarthritis ), chronic polyarthritis ( rheumatoid arthritis ) and ankylosing spondylitis ( ankylosing spondylitis ).
In April 2011, Pfizer withdrew the drug from the market in EU countries in the field of application approved under the trade name Onsenal for the treatment of patients with familial adenomatous polyposis ( FAP ) in addition to surgical therapy .
Contraindications (contraindications)
Hypersensitivity to sulfonamides , gastrointestinal bleeding , severe liver dysfunction, inflammatory gastrointestinal disease, severe renal insufficiency , heart failure , coronary artery disease , peripheral arterial disease and cerebrovascular disease preclude the use of celecoxib.
According to the CNT study, taking celecoxib increases the risk of upper gastrointestinal complications by 1.8 times.
Drug interactions
If oral anticoagulants are taken at the same time, there is an increased risk of bleeding, so the INR should be monitored especially at the start of treatment . Celecoxib can reduce the effects of diuretics and antihypertensive drugs .
Adverse effects (side effects)
Upper respiratory tract infections, insomnia, and dizziness are commonly observed. Occasionally, anemia , tinnitus, and urticaria occur. Rare side effects are ataxia , stomach ulcers , intestinal perforations , hair loss and increased sensitivity to light. Some studies have found an increased heart attack rate; a Swedish cohort study based on registry data of almost seven million people could not confirm an increased risk from COX-2 inhibitors. Celecoxib also inhibits the enzyme arachidonate-5-lipoxygenase (5-LO).
Pharmacological properties
When taken orally, celecoxib achieves a maximum bioavailability of 50–70%. Celecoxib reaches its maximum blood plasma concentration two to three hours after ingestion. Ingesting food that is too high in fat delays absorption by about an hour. Plasma protein binding is about 97%. The elimination half-life is six to twelve hours.
dosage
Celecoxib should be administered a maximum of every 12 hours. The (recommended) daily dose is thus 200–400 mg per day, the maximum daily dose is 400 mg.
Trade names
- Celebrex (Germany, Austria, Switzerland, monopreparation )
See also
further reading
- G. Rimon, RSSidhu, DA Lauver et al .: Coxibs interfere with the action of aspirin by binding tightly to one monomer of cyclooxygenase-1 . In: Proc Natl Acad Sci USA . December 2009. doi : 10.1073 / pnas.0909765106 . PMID 19955429 .
Individual evidence
- ↑ a b Celecoxib data sheet from Sigma-Aldrich , accessed on March 16, 2011 ( PDF ).
- ↑ http://www.docmorris.de/celebrex-200-mg-hartkapseln-kohlpharma-gmbh-kapseln-00172310-produktdetail
- ↑ Information letter on Onsenal (Celecoxib) deposited with the Medicines Commission of the German Medical Association (PDF; 1.6 MB) akdae.de. Retrieved July 1, 2012.
- ↑ a b c d Baron, Ralf, Koppert, Wolfgang, Strumpf, Michael, Willweber-Strumpf, Anne, Springer-Verlag GmbH: Practical pain medicine, interdisciplinary diagnostics - multimodal therapy. 4th edition 2019. Berlin, ISBN 978-3-662-57486-7 .
- ^ Caldwell B, Aldington S, Weatherall M, Shirtcliffe P, Beasley R: Risk of cardiovascular events and celecoxib: a systematic review and meta-analysis . In: JR Soc Med . 99, No. 3, March 2006, pp. 132-140. doi : 10.1258 / jrsm.99.3.132 . PMID 16508052 . PMC 1383759 (free full text).
- ^ Chen LC, Ashcroft DM: Risk of myocardial infarction associated with selective COX-2 inhibitors: meta-analysis of randomized controlled trials . In: Pharmacoepidemiol Drug Saf . 16, No. 7, July 2007, pp. 762-772. doi : 10.1002 / pds.1409 . PMID 17457957 .
- ↑ aerztezeitung.de Role backwards with COX-2 inhibitors, registry data from almost seven million people who had cardiovascular safety show no increased risk from COX-2 inhibitors.
- ↑ Maier TJ, Tausch L, Hoernig M, et al : Celecoxib inhibits 5-lipoxygenase . In: Biochem. Pharmacol. . 76, No. 7, October 2008, pp. 862-872. doi : 10.1016 / j.bcp.2008.07.009 . PMID 18692027 .
