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: OTC / Rx-only;
Pharmacokinetic data
Bioavailability	95% (by mouth)
Protein binding	99%
Metabolism	Liver (to 6-desmethylnaproxen)
Onset of action	1 hour
Elimination half-life	12–17 hours (adults)
Duration of action	12 hours
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 ;
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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. It is taken orally. It is available in immediate and delayed release formulations. Onset of effects is within an hour and lasts for up to twelve hours. Naproxen is also available in salt form, naproxen sodium, which has better solubility when taken orally.

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

Naproxen is a nonselective COX inhibitor. As an NSAID, naproxen appears to exert its anti-inflammatory action by reducing the production of inflammatory mediators called prostaglandins. It is metabolized by the liver to inactive metabolites.

Naproxen was patented in 1967 and approved for medical use in the United States in 1976. In the United States it is available over-the-counter and as a generic medication. In 2022, it was the 88th most commonly prescribed medication in the United States, with more than 7 million prescriptions.