Naproxen

Systematic (IUPAC) name
(+)-(S)-2-(6-methoxynaphthalen-2-yl) propanoic acid
Identifiers
CAS number	22204-53-1
ATC code	G02CC02 M01AE02, M02AA12
PubChem	CID 1302
DrugBank	APRD01135
ChemSpider	137720
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	12–24 hours
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	C(AU) B(US)
Legal status	Pharmacy Only (S2) (AU) P (UK) OTC (US) OTC(Ca)
Routes	Oral
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Naproxen sodium (INN) (pronounced /n?'pr?ks?n/) is a nonsteroidal anti-inflammatory drug (NSAID) commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and 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, Miranax, Naposin, Naprelan, Naprogesic, Naprosyn, Narocin, Proxen, Synflex, Xenobid.

Naproxen was 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, packets of 275 mg tablets of naproxen sodium are Schedule 2 Pharmacy Medicines, with a maximum daily dose of 5 tablets/1375 mg. In the UK, 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 July 14, 2009 with the exception of Quebec and Newfoundland and Labrador^[2], although it later became available without a prescription in these provinces.

[edit] 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 153 °C.

[edit] Synthesis

Naproxen has been produced by Syntex industrially as follows:^[3]

Other synthetic routes have also been discussed.^[3]

[edit] Adverse effects and warnings

Precautions should be used with the use of naproxen (and other NSAIDs) in patients with a past medical history of asthma, blood clotting, GI ulcers, GI bleeding, GI perforation, liver disease, kidney disease, hypertension or heart failure because naproxen may worsen these conditions. Discretion should be used in late-term pregnant women, anemic, dehydrated or elderly patients.^[4] The most common system to be affected by adverse reactions to naproxen is the gastrointestinal tract. As mentioned above, these adverse events includes GI bleeding and GI ulceration, and incidence of these reactions show a direct relationship both to dose as well as to duration of use.^[5][6] In addition, when taking naproxen, an individual may also experience blurred vision, confusion and drowsiness. It is advised that patients on naproxen use caution when driving or doing activities that require alertness.^[7]

In August 2006, the Journal Birth Defects Research Part B published results 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.^[8]

[edit] Drug Interactions

When naproxen is used in combination with methotrexate or aminoglycosides (for example, gentamicin) the blood levels of the methotrexate or aminoglycoside may increase, presumably because the elimination from the body is reduced. This may lead to more methotrexate or aminoglycoside-related side effects.^[9]

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 (Aspirin) (drugs may reduce each other's effects) or 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.

[edit] Naproxen link to Pseudoporphyria

Naproxen has also been linked to cases of pseudoporphyria, specifically in those with skin type II or lower, especially with blue or green eyes.

[edit] Risk of heart attack or stroke

This section requires expansion.

In 2004, 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 similar effects to Vioxx, such as heart attack or stroke, in patients taking naproxen.^[10]

[edit] See also

• Aspirin
• Paracetamol (acetaminophen)
• Ibuprofen

[edit] References

[edit] External links

Look up naproxen in Wiktionary, the free dictionary.

• 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

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Naproxen".