Systematic (IUPAC) name
propanoic acid
Clinical data
Pregnancy cat. C(AU) B(US)
Legal status Pharmacy Only (S2) (AU) P (UK) OTC (US) OTC(Ca)
Routes Oral
Pharmacokinetic data
Bioavailability 95% (oral)
Protein binding 99%
Metabolism Hepatic (to 6-desmethylnaproxen)
Half-life 12–24 hours
Excretion Renal
CAS number 22204-53-1 YesY
ATC code G02CC02 M01AE02, M02AA12
PubChem CID 156391
DrugBank APRD01135
ChemSpider 137720 YesY
KEGG D00118 YesY
Chemical data
Formula C14H14O3 
Mol. mass 230.259 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Naproxen sodium (INN) (play /nəˈprɒksən/) is a nonsteroidal anti-inflammatory drug (NSAID) commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as:

It is also used for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes. Naproxen and naproxen sodium are marketed under various trade names, including: Aleve, Anaprox, Antalgin, Feminax Ultra, Flanax, Inza, Midol Extended Relief, Nalgesin, Naposin, Naprelan, Naprogesic, Naprosyn, Narocin, Proxen, 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 Australia, packets of 275 mg tablets of naproxen sodium are Schedule 2 pharmacy medicines, with a maximum daily dose of 5 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.[1] Aleve became available over-the-counter in most provinces in Canada on 14 July 2009, it became available in Quebec during the summer of 2010 but can only be dispensed by a pharmacy employee after an assessment of the patient's needs. It most recently became available in British Columbia in March 2011. [2]


Risks and adverse effects

COX-2 selective and non-selective NSAIDs have been linked to increases in the number of serious and potentially fatal cardiovascular events such as myocardial infarctions and stroke. A 2011 meta-analysis published in the British Medical Journal states that, of all NSAIDs evaluated, naproxen was associated with the smallest overall cardiovascular risks.[3] 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.

NSAID Painkillers, such as Naproxen, may interfere and reduce efficiency of SSRI antidepressants [4][5]

Structure and details

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 152-154 °C.


Naproxen has been industrially produced by Syntex as follows:[6]

Large-Scale Synthesis of S-naproxen.png

Other synthetic routes have also been discussed.[6]

See also


External links

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Look at other dictionaries:

  • naproxen — [nə präk′sən] n. a white, crystalline powder, C14H14O3, used as a nonsteroidal, anti inflammatory drug to relieve pain and reduce fever, esp. in the treatment of arthritis, migraine, and menstrual cramps …   English World dictionary

  • Naproxen — Strukturformel Allgemeines Freiname Naproxen Andere Namen …   Deutsch Wikipedia

  • naproxen — n. an analgesic drug that also reduces inflammation and fever (see NSAID). It is used to treat rheumatoid arthritis, ankylosing spondylitis, and gout. It is administered by mouth; side effects may include digestive upsets and rashes: gastric… …   The new mediacal dictionary

  • naproxen sodium — [USP] the sodium salt of naproxen, having the same actions and uses as the base …   Medical dictionary

  • naproxen — /neuh prok seuhn/, n. Pharm. a nonsteroidal anti inflammatory substance, C14H14O3, used chiefly in the management of certain types of arthritis and as a painkiller. [by shortening and rearrangement of methoxy , naphthyl , and propionic,… …   Universalium

  • naproxen — noun /nəˈprɑksən/ A certain non steroidal anti inflammatory drug that inhibits the COX 1 and COX 2 enzymes and thereby reduces pain, fever, inflammation, and stiffness …   Wiktionary

  • naproxen — A nonsteroidal anti inflammatory analgesic agent used in the treatment of rheumatoid conditions. * * * na·prox·en nə präk sən n an anti inflammatory analgesic antipyretic drug C14H14O3 administered esp. to treat arthritis often in the form of its …   Medical dictionary

  • naproxen — n. nonsteroidal drug medication used to treat pain and reduce inflammation …   English contemporary dictionary

  • naproxen — [na prɒksɛn] noun Medicine a synthetic anti inflammatory drug used in the treatment of headaches and arthritis. Origin 1970s: from na(phthyl) + pr(opionic) + ox(y ), + en on the pattern of words such as tamoxifen …   English new terms dictionary

  • naproxen — na·prox·en …   English syllables

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