|Systematic (IUPAC) name|
|Trade names||Aleve, Naprelan, Naprosyn, Anaprox, Apronax|
|Licence data||US Daily Med:|
|Pregnancy cat.||C (AU) C (US)|
|Legal status||Pharmacy Only (S2) (AU) P (UK) OTC (US) OTC(Ca)|
|Metabolism||Hepatic (to 6-desmethylnaproxen)|
|ATC code||G02 M01, M02|
|Mol. mass||230.259 g/mol|
| (what is this?)
Naproxen is commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions including migraine, osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis and bursitis. It is also used for the treatment of primary dysmenorrhea.
COX-2 selective and nonselective NSAIDs have been linked to increases in the number of serious and potentially fatal cardiovascular events, such as myocardial infarctions and strokes. Naproxen is however associated with the smallest overall cardiovascular risks. The drug had roughly 50% of the associated risk of stroke as compared with ibuprofen and was also associated with a reduced number of myocardial infarctions as compared to control groups. As with other non-COX-2 selective NSAIDs, naproxen can cause gastrointestinal problems, such as heartburn, constipation, diarrhea, ulcers and stomach bleeding. Persons with a history of ulcers or inflammatory bowel disease should consult a doctor before taking naproxen.
It was found that high-dose naproxen induced near-complete suppression of platelet thromboxane throughout the dosing interval and appeared not to increase cardiovascular disease (CVD) risk, whereas other high-dose NSAID regimens had only transient effects on platelet COX-1 and were associated "with a small but definite vascular hazard". Conversely, naproxen was associated with higher rates of upper gastrointestinal bleeding complications in comparison to other NSAIDs.
Mechanism of action
Naproxen is a member of the 2-arylpropionic acid (profen) family of NSAIDs. The free acid is an odorless, white to off-white, crystalline substance. It is lipid-soluble and practically insoluble in water. It has a melting point of 152–155 °C.
Naproxen has been industrially produced by Syntex as follows:
Other synthetic routes have also been discussed.
Marketing and trade names
Naproxen and naproxen sodium are marketed under various trade names, including: Aleve, Anaprox, Antalgin, Apranax, Feminax Ultra, Flanax, Inza, Midol Extended Relief, Nalgesin, Naposin, Naprelan, Naprogesic, Naprosyn, Narocin, Proxen, Soproxen, Synflex and Xenobid.
Naproxen was originally marketed as the prescription drug Naprosyn by Syntex in 1976, and naproxen sodium was first marketed under the trade name Anaprox in 1980. It remains a prescription-only drug in much of the world. In the United States, the Food and Drug Administration (FDA) approved its use as an over-the-counter (OTC) drug in 1994; OTC preparations in the U.S. are mainly marketed by Bayer HealthCare under the trade name Aleve and generic store brand formulations in 220 mg tablets. In Australia, packets of 275 mg tablets of naproxen sodium are Schedule 2 pharmacy medicines, with a maximum daily dose of five tablets or 1375 mg. In the United Kingdom, 250-mg tablets of naproxen were approved for OTC sale under the brand name Feminax Ultra in 2008, for the treatment of primary dysmenorrhoea in women aged 15 to 50. In the Netherlands, 220mg and 275mg tablets are available OTC in drugstores, 550mg is OTC only at pharmacists. Aleve became available over-the-counter in most provinces in Canada on 14 July 2009, but not British Columbia, Quebec or Newfoundland and Labrador; it became available OTC in British Columbia in late January 2010.
Naproxen may have anti-viral activity against influenza. Specifically, it blocks the RNA-binding groove of the nucleoprotein of the virus, thereby preventing formation of the ribonucleoprotein complex, thus taking the vital nucleoproteins out of circulation.
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|Look up naproxen in Wiktionary, the free dictionary.|
- Aleve U.S.
- Aleve Canada
- CID 1302 from PubChem
- EINECS number 244-838-7
- MedlinePlus Information on naproxen
- FDA Statement on Naproxen, released 20 December 2004
- Alzheimer's Disease Anti-Inflammatory Prevention Trial
- Forbes article (expressing the point of view that the risk of heart attack or stroke was overstated)
- Which NSAID for Heart Disease Patients? – Medscape
- U.S. National Library of Medicine: Drug Information Portal – Naproxen
- Aleve Daily Med
- Naproxen bound to proteins in the PDB
- Use of naproxen in the Treatment of RSD