Naproxen

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Naproxen
Systematic (IUPAC) name
(+)-(S)-2-(6-methoxynaphthalen-2-yl)
propanoic acid
Identifiers
CAS number 22204-53-1
ATC code G02CC02 M01AE02, M02AA12
PubChem 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 /nəˈprɒksən/) is a non-steroidal anti-inflammatory drug (NSAID) commonly used for the reduction of mild to moderate pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, 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, Miranax, 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 British Columbia, Quebec and Newfoundland and Labrador.[2]

Contents

[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]

Large-Scale Synthesis of S-naproxen.png

Other synthetic routes have also been discussed.[3]

[edit] Adverse effects and warnings

IP110 Naproxen Tablets: 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.

In August 2006, the Journal Birth Defects Research Part B[4] 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.

[edit] IP110-Naproxen link to Pseudoporphyria

Naproxen IP110 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

The National Institutes of Health prematurely terminated a randomized clinical trial[5] 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.

[edit] See also

[edit] References

[edit] External links