Naproxen

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Naproxen
Naproxen2DACS.svg
Naproxen3d.png
Systematic (IUPAC) name
(+)-(S)-2-(6-methoxynaphthalen-2-yl)
propanoic acid
Clinical data
Trade names Aleve, Anaprox, Apronax, Naprelan, Naprosyn
AHFS/Drugs.com monograph
MedlinePlus a681029
Licence data US Daily Med:link
Pregnancy
category
  • AU: C
  • US: C (Risk not ruled out)
Legal status
  • AU: S2 (Pharmacy only)
  • CA: OTC
  • UK: Pharmacy medicines
  • US: OTC
  • In Australia it is only Schedule 2 when in preparations containing no more than 15 days' supply. Otherwise it is schedule 4 (prescription-only).[1]
Routes of
administration
Oral.
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 YesY
ATC code G02CC02 (WHO) M01AE02, M02AA12
PubChem CID: 156391
DrugBank DB00788 YesY
ChemSpider 137720 YesY
UNII 57Y76R9ATQ YesY
KEGG D00118 YesY
ChEBI CHEBI:7476 YesY
ChEMBL CHEMBL154 YesY
Chemical data
Formula C14H14O3
Molecular mass 230.259 g/mol
  • C[C@@H](c1ccc2cc(ccc2c1)OC)C(=O)O
  • 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 YesY
  • Key:CMWTZPSULFXXJA-VIFPVBQESA-N YesY
Physical data
Melting point 152–154 °C (306–309 °F)
  (verify)

Naproxen /nəˈprɒksən/ (INN; brand names: Aleve, Naprosyn and many others) is a non-selective COX inhibitor; usually sold as the sodium salt, is a nonsteroidal anti-inflammatory drug (NSAID) of the propionic acid class (which puts it in the same class as ibuprofen) and is commonly used for relief of a wide variety of pain, fever, swelling and stiffness.[2][3]:665,673

It is the preferred NSAID for long-term use in people with a high risk of cardiovascular (for example, heart attacks or strokes) complications,[3]:665 due to its relatively low risk of causing such complications. Naproxen has an intermediate risk of causing stomach ulcers as compared with ibuprofen, which is low risk, and indometacin, which is high risk.[4] In order to reduce the risk of stomach ulceration, it is often combined with a proton-pump inhibitor (a medication that reduces the production of stomach acid) during long-term treatment, in those with pre-existing stomach ulcers, or a history of developing stomach ulcers while on NSAIDs.[2][3]:665,673

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, among others. It is also used for the treatment of primary dysmenorrhea.[5]

Diagnostics

Naproxen has been utilized to differentiate between infectious fevers and those with neoplastic or connective tissue disease related fevers.[6]

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. Naproxen is, however, associated with the smallest overall cardiovascular risks.[7][8] Cardiovascular risk needs to be taken into account when prescribing any non-steroidal, anti-inflammatory drug. 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.[7] 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.

It was found that high-dose naproxen induced near-complete suppression of platelet thromboxane throughout the dosing interval and appeared not to increase cardiovascular disease (CVD) risk, whereas other high-dose NSAID regimens had only transient effects on platelet COX-1 and were associated "with a small but definite vascular hazard". Conversely, naproxen was associated with higher rates of upper gastrointestinal bleeding complications in comparison to other NSAIDs.[8]

NSAID painkillers, such as naproxen, may interfere with and reduce the efficacy of SSRI antidepressants.[10]

Mechanism of action

Naproxen works by reversibly inhibiting both the COX-1 and COX-2 enzymes.[11][12][13][14][15]

Compound information

Naproxen is a member of the 2-arylpropionic acid (profen) family of NSAIDs.[16] 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:[17]

Large-Scale Synthesis of S-naproxen.svg

Marketing and brand names

Naproxen and naproxen sodium are marketed under various brand names, including: Aleve, Accord, Anaprox, Antalgin, Apranax, Feminax Ultra, Flanax, Inza, Midol Extended Relief, Nalgesin, Naposin, Naprelan, Naprogesic, Naprosyn, Narocin, Pronaxen, Proxen, Soproxen, Synflex and Xenobid.

It is also available bundled with esomeprazole magnesium in delayed release tablets under the brand name Vimovo.[18]

Access restrictions

Naproxen was originally marketed as the prescription drug Naprosyn by Syntex in 1976, and naproxen sodium was first marketed under the brand 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 brand 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.[19] In the Netherlands, 220 mg and 275 mg tablets are available OTC in drugstores, 550 mg is OTC only at pharmacies. Aleve became available over-the-counter in most provinces in Canada on 14 July 2009, but not British Columbia, Quebec or Newfoundland and Labrador;[20] it subsequently became available OTC in British Columbia in late January 2010.[21]

Research

Naproxen may have anti-viral activity against influenza. Specifically, it blocks the RNA-binding groove of the nucleoprotein of the virus, thereby preventing formation of the ribonucleoprotein complex, thus taking the viral nucleoproteins out of circulation.[22]

Use in horses

Naproxen is given orally to horses at a dose of 10 mg/kg, and has shown to have a wide safety margin (no toxicity when given at 3-times the recommended dose of 42 days).[23] It is more effective for myositis than the commonly-used NSAID phenylbutazone, and has shown especially good results for treatment of equine exertional rhabdomyolysis,[24] but is less commonly used for musculoskeletal disease.

References

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  9. Naproxen. PubMed Health.
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  23. McIlwraith CW, Frisbie DD, Kawcak CE. Nonsteroidal Anti-Inflammatory Drugs. Proc. AAEP 2001 (47): 182-187.
  24. May SA, Lees P. Nonsteroidal anti-inflammatory drugs. In McIlwraith CW, Trotter GW, eds. Joint disease in the horse. Philadelphia: WB Saunders, 1996;223–237.

External links