Naproxen
| 240px | |
| 240px | |
| Systematic (IUPAC) name | |
|---|---|
|
(+)-(S)-2-(6-methoxynaphthalen-2-yl) propanoic acid | |
| Clinical data | |
| Pregnancy category | |
| Routes of administration | Oral |
| Legal status | |
| Legal status |
|
| Pharmacokinetic data | |
| Bioavailability | 95% (oral) |
| Protein binding | 99% |
| Metabolism | Hepatic (to 6-desmethylnaproxen) |
| Biological half-life | 12–24 hours |
| Excretion | Renal |
| Identifiers | |
| CAS Number | 22204-53-1 |
| ATC code | G02CC02 (WHO) M01AE02, M02AA12 |
| PubChem | CID 1302 |
| DrugBank | APRD01135 |
| ChemSpider | 137720 |
| Chemical data | |
| Formula | C14H14O3 |
| Molar mass | 230.259 g/mol[[Script error: No such module "String".]] |
| (verify) | |
Naproxen sodium (INN) (pronounced /nəˈprɒksən/) 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, Nalgesin, 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 British Columbia, Quebec and Newfoundland and Labrador,[2] although it later became available without a prescription in these provinces.
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.
Synthesis
Naproxen has been produced by Syntex industrially as follows:[3]
Other synthetic routes have also been discussed.[3]
See also
- Aspirin
- Paracetamol (acetaminophen)
- Ibuprofen
References
Cite error: Invalid <references> tag;
parameter "group" is allowed only.
<references />, or <references group="..." />External links
| 40x40px | 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
bs:Naproksen ca:Naproxén cs:Naproxen de:Naproxen es:Naproxeno fa:ناپروکسن fr:Naproxène it:Naprossene hu:Naproxén nl:Naproxen ja:ナプロキセン no:Naproksen ps:ناپروکسین pl:Naproksen pt:Naproxeno ro:Naproxen ru:Напроксен fi:Naprokseeni sv:Naproxen th:นาโปรเซน tr:Naproksen
zh:萘普生- ↑ Pocock, Nicola (2006). "MHRA approves availability of OTC naproxen (Feminax Ultra)". NHS Press Release.
- ↑ http://www.bayer.ca/files/Aleve%20Release.July14.FINAL_.pdf
- ↑ 3.0 3.1 Peter J. Harrington and Eric Lodewijk (1997). "Twenty Years of Naproxen Technology". Org. Process Res. Dev. 1 (1): 72–76. doi:10.1021/op960009e.
