Naproxen
Clinical data | |
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Pronunciation | /nəˈprɒksən/ |
Trade names | Aleve, Naprosyn, others[1][2] |
AHFS/Drugs.com | Monograph |
MedlinePlus | a681029 |
License data | |
Pregnancy category |
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Routes of administration | By mouth |
ATC code | |
Legal status | |
Legal status | |
Pharmacokinetic data | |
Bioavailability | 95% (by mouth) |
Protein binding | 99% |
Metabolism | Liver (to 6-desmethylnaproxen) |
Elimination half-life | 12–17 hours (adults)[7] |
Excretion | Kidney |
Identifiers | |
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JSmol) | |
Melting point | 152–154 °C (306–309 °F) |
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Naproxen, sold under the brand name Aleve among others, is a
Common side effects include dizziness,
Naproxen is a nonselective
Naproxen was patented in 1967, and approved for medical use in the United States in 1976.
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]
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250 mg tablet of naproxen
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220 mg tablet of naproxen sodium. Imprint L490 (upside-down). Round, light blue tablet.[16]
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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.
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-
Cardiovascular
A study found that high-dose naproxen induced near-complete suppression of platelet
Interactions
Drug–drug interactions
Naproxen may
NSAIDs such as naproxen may interfere with and reduce the efficacy of
Pharmacology
Mechanism of action
Naproxen works by
Pharmacokinetics
Naproxen is a minor substrate of
Pharmacogenetics
The
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
Society and culture
Brand names
Naproxen and naproxen sodium are marketed under various
Access restrictions
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).
References
- ^ a b c d e f "Naproxen". Drugs.com. 2017. Retrieved 7 February 2017.
- ^ a b c "Naproxen international". Drugs.com. 7 December 2020. Retrieved 3 January 2021.
- ^ "Naproxen Use During Pregnancy". Drugs.com. 13 August 2019. Retrieved 27 December 2019.
- FDA. Retrieved 22 October 2023.
- ISBN 978-1-74241-895-7.
- ^ "Boots Period Pain Relief 250 mg Gastro-Resistant Tablets - Summary of Product Characteristics (SmPC)". (emc). 4 February 2013. Retrieved 12 February 2023.
- ^ PMID 27826802.
- ^ a b c d e f g h i j k l m "Naproxen Monograph for Professionals". Drugs.com. AHFS. Retrieved 19 December 2018.
- ISBN 9781585280049.
- ^ 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.
- ISBN 9783527607495.
- ^ "Medicines A to Z - Naproxen". NHS. National Health Service. 24 October 2018. Retrieved 11 March 2020.
- ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
- ^ "Naproxen - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
- PMID 20352585. Retrieved 17 May 2017.
- ^ a b "L490 (Naproxen 220 mg)". drugs.com. Retrieved 17 May 2017.
- ^ "LACTMED: NAPROXEN". TOXNET. NIH. Retrieved 21 July 2017.
- PMID 7969358.
- PMID 22963024.
- ^ 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. This article incorporates text from this source, which is in the public domain.
- ^ a b "NSAIDs may cause rare kidney problems in unborn babies". U.S. Food and Drug Administration. 21 July 2017. Retrieved 15 October 2020. This article incorporates text from this source, which is in the public domain.
- ^ "Naproxen". PubMed Health. 1 September 2008. Archived from the original on 22 July 2010.
- ^ a b "How to take it". NHS.Gov. 20 January 2022.
- PMID 15194568.
- ISBN 978-0-9805790-9-3.
- ISBN 978-0-85711-084-8.
- PMID 27959716.
- ^ PMID 21224324. c7086.
- ^ PMID 23726390.
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- ^ S2CID 41772614.
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- S2CID 24736336. Archived from the originalon 23 February 2020. Retrieved 23 February 2020.
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- PMID 11566042.
- S2CID 35920001.
- ^ S2CID 5754183.
- PMID 2893700.
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- ^ "Vimovo- naproxen and esomeprazole magnesium tablet, delayed release". DailyMed. 2 August 2019. Retrieved 27 December 2019.
- ^ "Aleve- naproxen sodium tablet". DailyMed. 4 November 2019. Retrieved 27 December 2019.
- ^ "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.
- ^ "Aleve products released in Canada".
- ^ "Aleve – Welcome to Canada, Eh!" (PDF) (Press release). Bayer Health Care. 14 July 2009. Retrieved 24 March 2012.
- ^ "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.
- ^ "Industry Documents Library".
- . EurekAlert!.
- ISSN 0065-7182.
- ISBN 0-7216-5135-6.