Naproxen
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| Systematic (IUPAC) name |
(+)-(S)-2-(6-methoxynaphthalen-2-yl)
propanoic acid |
| Clinical data |
| Trade names |
Aleve |
| AHFS/Drugs.com |
monograph |
| MedlinePlus |
a681029 |
| Licence data |
US Daily Med:link |
| Pregnancy cat. |
C (AU) C (US) |
| Legal status |
Pharmacy Only (S2) (AU) P (UK) OTC (US) OTC(Ca) |
| Routes |
Oral |
| Pharmacokinetic data |
| Bioavailability |
95% (oral) |
| Protein binding |
99% |
| Metabolism |
Hepatic (to 6-desmethylnaproxen) |
| Half-life |
12–24 hours |
| Excretion |
Renal |
| Identifiers |
| CAS number |
22204-53-1 Y |
| ATC code |
G02CC02 M01AE02, M02AA12 |
| PubChem |
CID 156391 |
| DrugBank |
DB00788 |
| ChemSpider |
137720 Y |
| UNII |
57Y76R9ATQ Y |
| KEGG |
D00118 Y |
| ChEBI |
CHEBI:7476 Y |
| ChEMBL |
CHEMBL154 Y |
| Chemical data |
| Formula |
C14H14O3 |
| Mol. mass |
230.259 g/mol |
SMILES
- C[C@@H](c1ccc2cc(ccc2c1)OC)C(=O)O
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InChI
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InChI=1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)/t9-/m0/s1 Y
Key:CMWTZPSULFXXJA-VIFPVBQESA-N Y
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Y (what is this?) (verify)
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Naproxen sodium (INN) (pron.: /nəˈprɒksən/) is a nonsteroidal anti-inflammatory drug (NSAID). Naproxen and naproxen sodium are marketed under various trade names, including: Aleve, Anaprox, Antalgin, Apranax, Feminax Ultra, Flanax, Inza, Midol Extended Relief, Nalgesin, Naposin, Naprelan, Naprogesic, Naprosyn, Narocin, Proxen, Soproxen, Synflex and Xenobid.
Naproxen was originally marketed as the prescription drug Naprosyn by Syntex 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. In the United States, the Food and Drug Administration (FDA) approved its use as an over-the-counter (OTC) drug in 1994; OTC preparations in the U.S. are mainly marketed by Bayer HealthCare under the trade 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.[1] Aleve became available over-the-counter in most provinces in Canada on 14 July 2009, but not British Columbia or Newfoundland and Labrador;[2] it became available OTC in British Columbia in late January 2010.[3]
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Contents
- 1 Medical uses
- 2 Adverse effects
- 3 Compound information
- 4 Synthesis
- 5 See also
- 6 References
- 7 External links
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Medical uses
Naproxen is commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions including migraine, osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis and bursitis.[4] It is also used for the treatment of primary dysmenorrhea.[5]
Naproxen works by inhibiting both the COX-1 and COX-2 enzymes.[citation needed]
Clinical diagnostics
Naproxen has been utilized by some clinicians to differentiate between infectious fevers and those with neoplastic or connective tissue disease etiologies.[6][7]
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 2011 meta-analysis published in the British Medical Journal states, of all NSAIDs evaluated, naproxen was associated with the smallest overall cardiovascular risks.[8] The drug had roughly 50% of the associated risk of stroke as compared with ibuprofen and was also associated with a reduced number of myocardial infarctions as compared to control groups.[8] As with other non-COX-2 selective NSAIDs, naproxen can cause gastrointestinal problems, such as heartburn, constipation, diarrhea, ulcers and stomach bleeding.[9] Persons with a history of ulcers or inflammatory bowel disease should consult a doctor before taking naproxen. Consumption of alcohol may increase the risk of gastrointestinal complications.
NSAID painkillers, such as naproxen, may interfere with and reduce the efficiency of SSRI antidepressants.[10][11]
Compound information
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This section does not cite any references or sources. Please help improve this section by adding citations to reliable sources. Unsourced material may be challenged and removed. (May 2012) |
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 as follows:[12]
Other synthetic routes have also been discussed.[12]
See also
- Aspirin
- Ibuprofen
- Paracetamol
- Diclofenac
References
- ^ "Medicines regulator approves availability of a new OTC medicine for period pain" (PDF) (Press release). Medicines and Healthcare products Regulatory Agency (MHRA). 1 April 2008. http://www.mhra.gov.uk/home/idcplg?IdcService=GET_FILE&dDocName=CON014482&RevisionSelectionMethod=LatestReleased.
- ^ "ALEVE – Welcome to Canada, Eh!" (Press release). Bayer Health Care. 14 July 2009. http://www.bayer.ca/files/Aleve%20Release.July14.FINAL_.pdf. Retrieved 24 March 2012.
- ^ "ALEVE® - Helping British Columbians with Joint and Arthritis Pain Get Back to Doing the Activities They Love". http://www.newswire.ca/en/story/703499/aleve-r-helping-british-columbians-with-joint-and-arthritis-pain-get-back-to-doing-the-activities-they-love. Retrieved 26 September 2012.
- ^ "Body Aches No Fever". http://bodyachesnofever.net/. Retrieved 24 March 2012.[verification needed]
- ^ French L (January 2005). "Dysmenorrhea". Am Fam Physician 71 (2): 285–91. PMID 15686299. http://www.aafp.org/afp/2005/0115/p285.pdf.
- ^ Dy, Emmanuel Edwin R. The Naproxen Test as a Diagnostic Tool in the Causative Differentiation of Fever.
- ^ Zell JA, Chang JC. Neoplastic fever: a neglected paraneoplastic syndrome. PMID 15864658
- ^ a b Trelle S, Reichenbach S, Wandel S, Hildebrand P, Tschannen B, Villiger PM, Egger M, Jüni P. (2011). "Cardiovascular safety of non-steroidal anti-inflammatory drugs: network meta-analysis". BMJ 342: c7086. doi:10.1136/bmj.c7086. PMC 3019238. PMID 21224324. c7086. http://www.bmj.com/highwire/filestream/342854/field_highwire_article_pdf/0.pdf.
- ^ Naproxen. PubMed Health.
- ^ Why Painkillers Interfere with Anti-depressants
- ^ Warner-Schmidt JL; Vanover KE; Chen EY; Marshall JJ; Greengard P (May 2011). "Antidepressant effects of selective serotonin reuptake inhibitors (SSRIs) are attenuated by antiinflammatory drugs in mice and humans". Proc. Natl. Acad. Sci. U.S.A. 108 (22): 9262–7. doi:10.1073/pnas.1104836108. PMC 3107316. PMID 21518864. http://www.pnas.org/content/108/22/9262.full.pdf.
- ^ a b Peter J. Harrington and Eric Lodewijk (1997). "Twenty Years of Naproxen Technology". Org. Process Res. Dev. 1 (1): 72–76. doi:10.1021/op960009e.
External links
- Aleve U.S.
- Aleve Canada
- 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
- Aleve Daily Med
- Naproxen bound to proteins in the PDB
- Use of Naproxen in the Treatment of RSD
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Topical products for joint and muscular pain (M02)
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Anti-inflammatory preparations,
non-steroids |
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Butylpyrazolidines
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- Phenylbutazone
- Mofebutazone
- Clofezone
- Oxyphenbutazone
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|
|
Acetic acid derivatives
|
- Tolmetin
- Diclofenac
- Fentiazac
|
|
|
Other
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- Benzydamine
- Etofenamate
- Piroxicam
- Felbinac
- Bufexamac
- Ketoprofen
- Bendazac
- Naproxen
- Ibuprofen
- Feprazone
- Niflumic acid
- Meclofenamic acid
- Flurbiprofen
- Suxibuzone
- Indometacin
- Nifenazone
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| Capsaicin derivatives |
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| Other |
- Tolazoline
- Dimethyl sulfoxide
- Idrocilamide
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Prolactin inhibitors and anti-inflammatory products for vaginal administration (G02CB–G02CC)
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| Prolactin inhibitors |
- Bromocriptine
- Lisuride
- Cabergoline
- Quinagolide
- Metergoline
- Terguride
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Anti-inflammatory products
for vaginal administration |
- Ibuprofen
- Naproxen
- Benzydamine
- Flunoxaprofen
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