Naproxen

Naproxen
Clinical data
Pronunciation	/nəˈprɒksən/
Trade names	Aleve, Naprosyn, others
AHFS/Drugs.com	Monograph
MedlinePlus	a681029
License data	US DailyMed: Naproxen;
Pregnancy; category	AU: C; ;
Routes of; administration	By mouth
ATC code	G02CC02 (WHO) M01AE02 (WHO), M02AA12 (WHO), M01AE56 (WHO), M01AE52 (WHO);
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).; CA: OTC; UK: POM (Prescription only) / P; US: WARNINGOTC / Rx-only;
Pharmacokinetic data
Bioavailability	95% (by mouth)
Protein binding	99%
Metabolism	Liver (to 6-desmethylnaproxen)
Elimination half-life	12–17 hours (adults)
Excretion	Kidney
Identifiers
	IUPAC name (+)-(S)-2-(6-Methoxynaphthalen-2-yl)propanoic acid;
CAS Number	22204-53-1 ;
PubChem CID	156391;
DrugBank	DB00788 ;
ChemSpider	137720 ;
UNII	57Y76R9ATQ;
KEGG	D00118 ; as salt: D00970 ;
ChEBI	CHEBI:7476 ;
ChEMBL	ChEMBL154 ;
PDB ligand	NPX (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID4040686 ;
ECHA InfoCard	100.040.747
Chemical and physical data
Formula	C14H14O3
Molar mass	230.263 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	152–154 °C (306–309 °F)
	SMILES COc1cc2ccc(cc2cc1)[C@H](C)C(=O)O;
	InChI 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 ; Key:CMWTZPSULFXXJA-VIFPVBQESA-N ;
	(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]

^ Cite error: The named reference drugs was invoked but never defined (see the help page).
^ Cite error: The named reference Naproxen international was invoked but never defined (see the help page).
^ "Naproxen Use During Pregnancy". Drugs.com. 13 August 2019. Retrieved 27 December 2019.
^ "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.
^ 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.
^ "Boots Period Pain Relief 250 mg Gastro-Resistant Tablets - Summary of Product Characteristics (SmPC)". (emc). 4 February 2013. Retrieved 12 February 2023.
^ Cite error: The named reference CV Safety Review Article was invoked but never defined (see the help page).
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m "Naproxen Monograph for Professionals". Drugs.com. AHFS. Retrieved 19 December 2018.
^ Mason L, Edwards JE, Moore RA, McQuay HJ (October 2004). Mason L (ed.). "Single dose oral naproxen and naproxen sodium for acute postoperative pain". The Cochrane Database of Systematic Reviews (4): CD004234. doi:10.1002/14651858.CD004234.pub2. PMC 4164452. PMID 15495091.
^ McEvoy GK (2000). AHFS Drug Information, 2000. American Society of Health-System Pharmacists. p. 1854. ISBN 9781585280049.
^ "Naprosyn- naproxen tablet EC-Naprosyn- naproxen tablet, delayed release Anaprox DS- naproxen sodium tablet". DailyMed. 1 July 2019. Retrieved 27 December 2019.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 520. ISBN 9783527607495.
^ "Medicines A to Z - Naproxen". NHS. National Health Service. 24 October 2018. Retrieved 11 March 2020.
^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
^ "Naproxen Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.

[drugs-1] Cite error: The named reference drugs was invoked but never defined (see the help page).

[Naproxen_international-2] Cite error: The named reference Naproxen international was invoked but never defined (see the help page).

[Drugs.com_pregnancy-3] "Naproxen Use During Pregnancy". Drugs.com. 13 August 2019. Retrieved 27 December 2019.

[FDA-AllBoxedWarnings-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.

[CV_Safety_Review_Article-7] Cite error: The named reference CV Safety Review Article was invoked but never defined (see the help page).

[AHFS2018-8] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m "Naproxen Monograph for Professionals". Drugs.com. AHFS. Retrieved 19 December 2018.

[Mason-9] Mason L, Edwards JE, Moore RA, McQuay HJ (October 2004). Mason L (ed.). "Single dose oral naproxen and naproxen sodium for acute postoperative pain". The Cochrane Database of Systematic Reviews (4): CD004234. doi:10.1002/14651858.CD004234.pub2. PMC 4164452. PMID 15495091.

[10] McEvoy GK (2000). AHFS Drug Information, 2000. American Society of Health-System Pharmacists. p. 1854. ISBN 9781585280049.

[Naprosyn_label-11] "Naprosyn- naproxen tablet EC-Naprosyn- naproxen tablet, delayed release Anaprox DS- naproxen sodium tablet". DailyMed. 1 July 2019. Retrieved 27 December 2019.

[Fis2006-12] 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.

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Naproxen

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