Naproxen
From Wikipedia, the free encyclopedia
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| Systematic (IUPAC) name | |
|---|---|
| (+)-(S)-2-(6-methoxynaphthalen-2-yl) propanoic acid |
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| 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. | |
| Legal status | |
| 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]
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[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
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
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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
- Aspirin
- Paracetamol (acetaminophen)
- Ibuprofen
[edit] References
- ^ Pocock, Nicola (2006). "MHRA approves availability of OTC naproxen (Feminax Ultra)". NHS Press Release. http://www.druginfozone.nhs.uk/Record%20Viewing/viewRecord.aspx?id=591725.
- ^ http://www.bayer.ca/files/Aleve%20Release.July14.FINAL_.pdf
- ^ a b Peter J. Harrington and Eric Lodewijk (1997). "Twenty Years of Naproxen Technology". Org. Process Res. Dev. 1 (1): 72–76. doi:.
- ^ Ofori, et al. (August 2006). "Risk of congenital anomalies in pregnant users of non-steroidal anti-inflammatory drugs: a nested case-control study". Birth Defects Research Part B: Developmental and Reproductive Toxicology. http://www3.interscience.wiley.com/journal/112752202/abstract.
- ^ ADAPT Research Group (2006). "Cardiovascular and Cerebrovascular Events in the Randomized, Controlled Alzheimer's Disease Anti-Inflammatory Prevention Trial (ADAPT)". PLoS Clinical Trials. http://clinicaltrials.plosjournals.org/perlserv/?request=get-document&doi=10.1371/journal.pctr.0010033.
[edit] External links
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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
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