Naproxen sodium (INN) (pron.: /nəˈprɒksən/) is a nonsteroidal anti-inflammatory drug (NSAID). 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. 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 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.
Naproxen works by inhibiting both the COX-1 and COX-2 enzymes.
A study from 2013 shows that Naproxen might have anti-viral activity against flu. Specifically it blocks the RNA binding groove of the virus' nucleoprotein, preventing formation of the ribonucleoprotein complex, thus taking the vital nucleoproteins out of circulation.
Naproxen has been utilized by some clinicians to differentiate between infectious fevers and those with neoplastic or connective tissue disease etiologies.
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. A 2011 meta-analysis published in the British Medical Journal states, of all NSAIDs evaluated, naproxen was 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. Consumption of alcohol may increase the risk of gastrointestinal complications.
NSAID painkillers, such as naproxen, may interfere with and reduce the efficiency of SSRI antidepressants.
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.
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