My watch list  


Systematic (IUPAC) name
propanoic acid
CAS number 22204-53-1
ATC code G02CC02 M01AE02, M02AA12
PubChem 1302
DrugBank APRD01135
Chemical data
Formula C14H14O3 
Mol. mass 230.259 g/mol
Pharmacokinetic data
Bioavailability 95% (oral)
Protein binding 99%
Metabolism Hepatic (to 6-desmethylnaproxen)
Half life 12–15 hours
Excretion Renal
Therapeutic considerations
Pregnancy cat.


Legal status

Pharmacy Only (S2)(AU) POM(UK) OTC(US)

Routes Oral

Naproxen (INN) (pronounced /nəˈprɒksən/) is a non-steroidal anti-inflammatory drug (NSAID) commonly used for the reduction of moderate to severe pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, injury (like fractures), menstrual cramps, tendinitis, bursitis, and the treatment of primary dysmenorrhea. Naproxen and naproxen sodium are marketed under various trade names including: Aleve, Anaprox, Miranax, Naprogesic, Naprosyn, Naprelan, Synflex.

Naproxen was first and originally marketed as the prescription drug Naprosyn 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. The U.S. Food and Drug Administration (FDA) approved the use of naproxen sodium as an over-the-counter (OTC) drug in 1994, where OTC preparations are sold under the trade name Aleve. In Australia, small packets of lower-strength preparations of naproxen sodium are Schedule 2 Pharmacy Medicines.

Structure and details

Naproxen is a member of the 2-arylpropionic acid (profen) family of NSAIDs. It is an odorless, white to off-white crystalline substance. It is lipid-soluble and practically insoluble in water. It has a melting point of 153 °C.

Adverse effects and warnings

Like other NSAIDs, naproxen is capable of producing disturbances in the gastrointestinal tract. Addition of a proton pump inhibitor such as esomeprazole will prevent this adverse effect. Naproxen in combination with a proton pump inhibitor is the safest NSAID combination.[citation needed]

Also like other NSAIDs, naproxen can inhibit the excretion of sodium and lithium. Extreme care must be taken by those who use this drug along with lithium supplements. Naproxen is also not recommended for use with NSAIDs of the salicylate family (drugs may reduce each other's effects), nor with anticoagulants (may increase risk of bleeding). Naproxen preparations containing sodium (e.g., Anaprox, Aleve, etc.) are not recommended for use in patients with sodium-sensitive hypertension, due to potential adverse effects on blood pressure in this small subset of hypertensive patients.

In August 2006, the journal Birth Defects Research Part B published results in the September issue indicating that pregnant women who take NSAIDs including naproxen in the first trimester run an increased risk of having a child with congenital birth defects, particularly heart anomalies.

Risk of heart attack or stroke

The National Institutes of Health prematurely terminated a randomized clinical trial of naproxen and celecoxib for prevention of Alzheimer's disease, after preliminary data suggested an increased risk of major cardiovascular events, such as heart attack or stroke, in patients taking naproxen. However, recent meta-analyses which took into account all data from significant clinical trials of naproxen, including randomized clinical trials and observational trials concluded that naproxen carries no increased risk of heart attack or stroke at any commonly used dose. This stands in contrast to other NSAIDS, such as rofecoxib (Vioxx), celecoxib (Celebrex), and diclofenac, which did show significantly increased risk at some or all dosages. In February of 2007, the American Heart Association released a scientific statement advising that, when possible, physicians should avoid using NSAIDs in patients at high risk for heart disease. When pain relief is necessary, the AHA advises that doctors should preferentially use acetaminophen or certain older, non-COX-2 selective NSAIDs.

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Naproxen". A list of authors is available in Wikipedia.
Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE