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Naproxen (brand names: Aleve, Naprosyn, and many others) is a nonsteroidal anti-inflammatory drug (NSAID) of the propionic acid class (the same class as ibuprofen ) that relieves pain, fever, swelling, and stiffness. It is a nonselective COX inhibitor, usually sold as the sodium salt. It is available in both an immediate release and extended release formulation. Naproxen is generally safe for use by breastfeeding mothers.
Common adverse effects of naproxen include central nervous system effects (e.g. dizziness and headache), blood effects (e.g. bruising), allergic reactions (e.g. rash), and gastrointestinal complaints (e.g. heartburn and stomach ulcers). It has an intermediate risk of stomach ulcers compared to others drugs in the same class (NSAIDs). NSAIDs appear to increase the risk of serious cardiovascular events, though this risk appears to be less with naproxen compared to other NSAIDs. Serious drug interactions may occur in combinations with other drugs that affect the blood, or with drugs that also increase the risk of ulcers.
As an NSAID, naproxen exerts its anti-inflammatory action by reducing the production of inflammatory mediators called prostaglandins. It is extensively metabolized by the liver to inactive metabolites.
Contents
1 Medical uses
1.1 Available formulations
1.2 Specific populations
1.2.1 Pregnancy and lactation
1.3 Diagnostics
2 Adverse effects
2.1 Gastrointestinal adverse effects
2.2 Cardiovascular adverse effects
3 Interactions
3.1 Drug–drug interactions
3.2 Drug–food interactions
4 Pharmacology
4.1 Mechanism of action
4.2 Pharmacokinetics
4.3 Pharmacogenetics
5 Chemistry
5.1 Synthesis
6 Society and culture
6.1 Brand names
7 Access restrictions
8 Research
9 Veterinary use
9.1 Use in horses
10 References
11 External links
Medical uses
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Naproxen’s medical uses are related to its mechanism of action as an anti-inflammatory compound. Naproxen is used to treat a variety of inflammatory conditions and symptoms that are due to excessive inflammation, such as pain and fever (naproxen has fever-reducing, or antipyretic, properties in addition to its anti-inflammatory activity). Notably, not all medications that reduce fever are anti-inflammatory compounds (such as paracetamol ). Inflammatory sources of pain that may respond to naproxen’s anti-inflammatory activity are conditions such as migraine, osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, and bursitis.
Because of its anti-inflammatory mechanism of action, one would not expect naproxen to be useful in treating non-inflammatory causes of pain (e.g., diabetic nerve pain ).
Naproxen sodium is used as a “bridge therapy” in medication-overuse headache to slowly take patients off of other medications.
Available formulations
Naproxen sodium is available as both an immediate release and as an extended release tablet. The extended release formulations (sometimes called “sustained release,” or “enteric coated”) take longer to take effect than the immediate release formulations, and therefore are less useful when immediate pain relief is desired. Extended release formulations are more useful for the treatment of chronic, or long-lasting, conditions, in which long-term pain relief is desirable.
Naproxen extended release 500 mg, back and front.
Specific populations
Pregnancy and lactation
Small amounts of naproxen are excreted in breast milk.
Diagnostics
Naproxen has been used to differentiate between infectious fevers and neoplastic or connective tissue disease -related fevers.
Adverse effects
Common adverse effects include dizziness, drowsiness, headache, rash, bruising, and gastrointestinal upset.
Gastrointestinal adverse effects
As with other non-COX-2 selective NSAIDs, naproxen can cause gastrointestinal problems, such as heartburn, constipation, diarrhea, ulcers and stomach bleeding.
Cardiovascular adverse effects
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 study 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 non-aspirin 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 compared with other NSAIDs.
Interactions
Drug–drug interactions
Naproxen may interact with antidepressants, lithium, methotrexate, probenecid, warfarin and other blood thinners, heart or blood pressure medications, including diuretics, or steroid medicines such as prednisone.
NSAIDs such as naproxen may interfere with and reduce the efficacy of SSRI antidepressants,
Drug–food interactions
Alcohol consumption increases the risk of gastrointestinal bleeding when combined with NSAIDs like naproxen in a dose-dependent manner (that is, the higher the dose of naproxen, the higher the risk of bleeding).
Pharmacology
Mechanism of action
Naproxen works by reversibly inhibiting both the COX-1 and COX-2 enzymes as a non-selective coxib. This results in the inhibition of prostaglandin synthesis. Prostaglandins act as signaling molecules in the body, inducing inflammation. Thus, by inhibiting COX-1/2, naproxen induces an anti-inflammatory effect.
Pharmacokinetics
Naproxen is a minor substrate of CYP1A2 and CYP2C9. It is extensively metabolized in the liver to 6-O-desmethylnaproxen, and both the parent drug and the desmethyl metabolite undergo further metabolism to their respective acylglucuronide conjugated metabolites.
Pharmacogenetics
The pharmacogenetics of naproxen has been studied in an effort to better understand its adverse effects.
As of October 2017, there are no recommendations for routine CYP2C9 testing for naproxen.
Chemistry
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.
Synthesis
Naproxen has been industrially produced by Syntex starting from 2-naphthol as follows:
Society and culture
Brand names
Naproxen and naproxen sodium are marketed under various brand names, including: Synflex, Aleve, Accord, Anaprox, Antalgin, Apranax, Feminax Ultra, Flanax, Inza, Maxidol, Midol Extended Relief, Nalgesin, Naposin, Naprelan, Naprogesic, Naprosyn, Narocin, Pronaxen, Proxen, Soproxen, MotriMax, and Xenobid.
Access restrictions
Syntex first marketed naproxen in 1976 as the prescription drug Naprosyn. They first marketed naproxen sodium under the brand 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 it as an over-the-counter (OTC) drug in 1994. OTC preparations in the U.S. are mainly marketed by Bayer HealthCare under the brand 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.
Research
Naproxen may have antiviral activity against influenza. In laboratory research, it blocks the RNA-binding groove of the nucleoprotein of the virus, preventing formation of the ribonucleoprotein complex—thus taking the viral nucleoproteins out of circulation.
Veterinary use
Use in horses
Naproxen is given orally to horses at a dose of 10 mg/kg, and has shown to have a wide safety margin (no toxicity when given at three times the recommended dose for 42 days). a disease of muscle breakdown, but is less commonly used for musculoskeletal disease.

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