Naproxen

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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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.040.747 Edit this at Wikidata
Chemical and physical data
FormulaC14H14O3
Molar mass230.263 g·mol−1
3D model (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 nonsteroidal anti-inflammatory drug (NSAID) used to treat pain, menstrual cramps, and 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] Naproxen is also available in salt form, naproxen sodium, which has better solubility when taken orally.[9]

Common side effects include dizziness, headache, bruising, allergic reactions, heartburn, and stomach pain.[8] Severe side effects include an increased risk of heart disease, stroke, gastrointestinal bleeding, and stomach ulcers.[8] The heart disease risk may be lower than with other NSAIDs.[8] It is not recommended in people with kidney problems.[8] Use is not recommended in the third trimester of pregnancy.[8]

Naproxen is a nonselective COX inhibitor.[8] As an NSAID, naproxen appears to exert its anti-inflammatory action by reducing the production of inflammatory mediators called prostaglandins.[10] 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.[11][8][12] In the United States it is available over the counter and as a generic medication.[8][13] In 2022, it was the 88th most commonly prescribed medication in the United States, with more than 7 million prescriptions.[14][15]

  1. ^ Cite error: The named reference drugs was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference Naproxen international was invoked but never defined (see the help page).
  3. ^ "Naproxen Use During Pregnancy". Drugs.com. 13 August 2019. Retrieved 27 December 2019.
  4. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  5. ^ Gill, A, ed. (July 2013). Standard for the Uniform Scheduling of Medicines and Poisons No. 4 (PDF). Therapeutic Goods Administration. ISBN 978-1-74241-895-7.
  6. ^ "Boots Period Pain Relief 250 mg Gastro-Resistant Tablets - Summary of Product Characteristics (SmPC)". (emc). 4 February 2013. Retrieved 12 February 2023.
  7. ^ Cite error: The named reference CV Safety Review Article was invoked but never defined (see the help page).
  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. ^ Derry C, Derry S, Moore RA, McQuay HJ (January 2009). "Single dose oral naproxen and naproxen sodium for acute postoperative pain in adults". The Cochrane Database of Systematic Reviews. 2009 (1): CD004234. doi:10.1002/14651858.CD004234.pub3. PMC 6483469. PMID 19160232.
  10. ^ McEvoy GK (2000). AHFS Drug Information, 2000. American Society of Health-System Pharmacists. p. 1854. ISBN 9781585280049.
  11. ^ "Naprosyn- naproxen tablet EC-Naprosyn- naproxen tablet, delayed release Anaprox DS- naproxen sodium tablet". DailyMed. 1 July 2019. Retrieved 27 December 2019.
  12. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 520. ISBN 9783527607495.
  13. ^ "Medicines A to Z - Naproxen". NHS. National Health Service. 24 October 2018. Retrieved 11 March 2020.
  14. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  15. ^ "Naproxen Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.