Naproxen

Source: Wikipedia, the free encyclopedia.

Naproxen
Clinical data
Pronunciation/nəˈprɒksən/
Trade namesAleve, Naprosyn, others[1][2]
AHFS/Drugs.comMonograph
MedlinePlusa681029
License data
Pregnancy
category
Routes of
administration
By mouth
ATC code
Legal status
Legal status
  • AU: S2 (Pharmacy medicine) when in preparations that contain no more than 15 days' supply. Otherwise it is Schedule 4 (Prescription only).[5]
  • CA: OTC
  • UK: POM (Prescription only) / P[6]
  • US: WARNING[4]OTC / Rx-only
Pharmacokinetic data
Bioavailability95% (by mouth)
Protein binding99%
MetabolismLiver (to 6-desmethylnaproxen)
Elimination half-life12–17 hours (adults)[7]
ExcretionKidney
Identifiers
  • (+)-(S)-2-(6-Methoxynaphthalen-2-yl)propanoic acid
JSmol)
Melting point152–154 °C (306–309 °F)
  • COc1cc2ccc(cc2cc1)[C@H](C)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 checkY
  • Key:CMWTZPSULFXXJA-VIFPVBQESA-N checkY
  (verify)

Naproxen, sold under the brand name Aleve among others, is a

inflammatory diseases such as rheumatoid arthritis, gout and fever.[8] It is taken orally.[8] It is available in immediate and delayed release formulations.[8] Onset of effects is within an hour and lasts for up to twelve hours.[8]

Common side effects include dizziness,

Naproxen is a nonselective

prostaglandins.[9] It is metabolized by the liver to inactive metabolites.[8]

Naproxen was patented in 1967, and approved for medical use in the United States in 1976.

generic medication.[8][12] In 2021, it was the 93rd most commonly prescribed medication in the United States, with more than 7 million prescriptions.[13][14]

Medical uses

Naproxen's medical uses are related to its mechanism of action as an anti-inflammatory compound.

Naproxen sodium is used as a "bridge therapy" in medication-overuse headache to slowly take patients off other medications.[15]

Available formulations

Naproxen sodium is available as both an immediate release and as an extended release tablet. The extended release formulations (sometimes called "sustained release", or "enteric coated") take longer to take effect than the immediate release formulations, and therefore are less useful when immediate pain relief is desired. Extended release formulations are more useful for the treatment of chronic, or long-lasting, conditions, in which long-term pain relief is desirable.[16]

  • 250 mg tablet of naproxen
    250 mg tablet of naproxen
  • 220 mg tablet of naproxen sodium. Imprint L490 (upside-down). Round, light blue tablet.[16]
    220 mg tablet of naproxen sodium. Imprint L490 (upside-down). Round, light blue tablet.[16]
  • Naproxen extended release 500 mg, back and front
    Naproxen extended release 500 mg, back and front

Pregnancy and lactation

As with all non-steroidal anti-inflammatory medications (NSAIDs), naproxen use should be avoided in pregnancy due to the importance of prostaglandins in vascular and renal function in the fetus. NSAIDs should especially be avoided in the third trimester. Small amounts of naproxen are excreted in breast milk.[1] However, adverse effects are uncommon in infants breastfed from a mother taking naproxen.[17]

Adverse effects

Common adverse effects include dizziness, drowsiness, headache, rash, bruising, and gastrointestinal upset.

muscle cramps in the legs in 3% of people.[19]

In October 2020, the U.S. Food and Drug Administration (FDA) required the drug label to be updated for all nonsteroidal anti-inflammatory medications to describe the risk of kidney problems in unborn babies that result in low amniotic fluid.[20][21] They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.[20][21]

Gastrointestinal

As with other non-

stomach acid production) during long-term treatment of those with pre-existing stomach ulcers or a history of developing stomach ulcers while on NSAIDs.[25][26]

Cardiovascular

myocardial infarctions and strokes.[27] Naproxen is, however, associated with the smallest overall cardiovascular risks.[28][29] Cardiovascular risk must be considered when prescribing any nonsteroidal anti-inflammatory drug. The drug had roughly 50% of the associated risk of stroke compared with ibuprofen, and was also associated with a reduced number of myocardial infarctions compared with control groups.[28]

A study found that high-dose naproxen induced near-complete suppression of 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 compared with other NSAIDs.[29]

Interactions

Drug–drug interactions

Naproxen may

blood thinners, heart or blood pressure medications, including diuretics, or steroid medicines such as prednisone.[1]

NSAIDs such as naproxen may interfere with and reduce the efficacy of

SSRI antidepressants,[30] as well as increase the risk of bleeding greater than the individual bleeding risk of either class of agent, when taken together.[31] Naproxen is not contraindicated in the presence of SSRIs, though concomitant use of the medications should be done with caution.[31] Alcohol consumption increases the risk of gastrointestinal bleeding when combined with NSAIDs like naproxen in a dose-dependent manner (that is, the higher the dose of naproxen, the higher the risk of bleeding).[32] The risk is highest for people who are heavy drinkers.[32]

Pharmacology

Mechanism of action

Naproxen works by

Pharmacokinetics

Naproxen is a minor substrate of

clinical trials shows that naproxen's time to peak plasma concentration occurs between 2 and 4 hours after oral administration, though naproxen sodium reaches peak plasma concentrations within 1–2 hours.[7][clarification needed
]

Pharmacogenetics

The

homozygous defective variants.[39]

Chemistry

Naproxen is a member of the 2-arylpropionic acid (profen) family of NSAIDs.[40] The free acid is an odorless, white to off-white crystalline substance.[citation needed] It is lipid-soluble and practically insoluble in water. It has a melting point of 152–155 °C.[citation needed]

Synthesis

Naproxen has been industrially produced by

2-naphthol as follows:[41]

"Pope-Peach" should read "Pope-Peachey"

Society and culture

Brand names

Naproxen and naproxen sodium are marketed under various

naproxen/esomeprazole magnesium in delayed release tablets under the brand name Vimovo.[2][42]

Access restrictions

dysmenorrhoea in women aged 15 to 50.[44] 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 some provinces in Canada[45] on 14 July 2009, but not British Columbia, Quebec or Newfoundland and Labrador;[46] it subsequently became available OTC in British Columbia in January 2010.[47]

Toxicology scandal

Naproxen was one of the four substances named in the prosecution of Industrial Bio-Test Laboratories (IBT) for fraudulent toxicology testing.[48] Naproxen passed subsequent legitimate toxicology testing.

Research

Naproxen may have antiviral activity against influenza. In laboratory research, it blocks the RNA-binding groove of the nucleoprotein of the virus, preventing formation of the ribonucleoprotein complex—thus taking the viral nucleoproteins out of circulation.[49]

Veterinary use

Horses

Naproxen is given by mouth to horses at a dose of 10 mg/kg, and has shown to have a wide safety margin (no toxicity when given at three times the recommended dose for 42 days).

musculoskeletal disease.[medical citation needed
]

References

  1. ^ a b c d e f "Naproxen". Drugs.com. 2017. Retrieved 7 February 2017.
  2. ^ a b c "Naproxen international". Drugs.com. 7 December 2020. Retrieved 3 January 2021.
  3. ^ "Naproxen Use During Pregnancy". Drugs.com. 13 August 2019. Retrieved 27 December 2019.
  4. FDA
    . Retrieved 22 October 2023.
  5. .
  6. ^ "Boots Period Pain Relief 250 mg Gastro-Resistant Tablets - Summary of Product Characteristics (SmPC)". (emc). 4 February 2013. Retrieved 12 February 2023.
  7. ^
    PMID 27826802
    .
  8. ^ a b c d e f g h i j k l m "Naproxen Monograph for Professionals". Drugs.com. AHFS. Retrieved 19 December 2018.
  9. .
  10. ^ a b c d e "Naprosyn- naproxen tablet EC-Naprosyn- naproxen tablet, delayed release Anaprox DS- naproxen sodium tablet". DailyMed. 1 July 2019. Retrieved 27 December 2019.
  11. .
  12. ^ "Medicines A to Z - Naproxen". NHS. National Health Service. 24 October 2018. Retrieved 11 March 2020.
  13. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  14. ^ "Naproxen - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  15. PMID 20352585
    . Retrieved 17 May 2017.
  16. ^ a b "L490 (Naproxen 220 mg)". drugs.com. Retrieved 17 May 2017.
  17. ^ "LACTMED: NAPROXEN". TOXNET. NIH. Retrieved 21 July 2017.
  18. PMID 7969358
    .
  19. .
  20. ^ a b "FDA Warns that Using a Type of Pain and Fever Medication in Second Half of Pregnancy Could Lead to Complications". U.S. Food and Drug Administration (FDA) (Press release). 15 October 2020. Retrieved 15 October 2020. Public Domain This article incorporates text from this source, which is in the public domain.
  21. ^ a b "NSAIDs may cause rare kidney problems in unborn babies". U.S. Food and Drug Administration. 21 July 2017. Retrieved 15 October 2020. Public Domain This article incorporates text from this source, which is in the public domain.
  22. ^ "Naproxen". PubMed Health. 1 September 2008. Archived from the original on 22 July 2010.
  23. ^ a b "How to take it". NHS.Gov. 20 January 2022.
  24. PMID 15194568
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  35. S2CID 24736336. Archived from the original
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  42. ^ "Vimovo- naproxen and esomeprazole magnesium tablet, delayed release". DailyMed. 2 August 2019. Retrieved 27 December 2019.
  43. ^ "Aleve- naproxen sodium tablet". DailyMed. 4 November 2019. Retrieved 27 December 2019.
  44. ^ "Medicines regulator approves availability of a new OTC medicine for period pain" (Press release). Medicines and Healthcare products Regulatory Agency (MHRA). 1 April 2008. Archived from the original (PDF) on 21 September 2013.
  45. ^ "Aleve products released in Canada".
  46. ^ "Aleve – Welcome to Canada, Eh!" (PDF) (Press release). Bayer Health Care. 14 July 2009. Retrieved 24 March 2012.
  47. ^ "Aleve – Helping British Columbians with Joint and Arthritis Pain Get Back to Doing the Activities They Love". newswire.ca. 28 January 2010. Archived from the original on 21 September 2013. Retrieved 27 September 2012.
  48. ^ "Industry Documents Library".
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External links