Naprosyn

Naproxen

Clinical data
Pronunciation	/nəˈprɒksən/
Trade names	Aleve, Naprosyn, Anaprox, Naprelan, Flanax, Aflaxen, others
AHFS/Drugs.com	Monograph
MedlinePlus	a681029
License data	US DailyMed: 43871
Pregnancy category	AU: C US: C (Risk not ruled out)
Routes of administration	Oral
ATC code	G02CC02 (WHO) M01AE02 (WHO), M02AA12 (WHO)
Legal status
Legal status	AU: S2 (Pharmacy only) when in preparations that contain no more than 15 days' supply. Otherwise it is Schedule 4 (Prescription only). CA: OTC UK: POM (Prescription only) Pharmacy medicine (P) only for treatment of primary dysmenorrhoea in women aged 15-50 years subject to a maximum single dose of 500mg, maximum daily dose of 750mg for a maximum of 3 days, and max pack size of 9x250mg tablets US: OTC
Pharmacokinetic data
Bioavailability	95% (oral)
Protein binding	99%
Metabolism	Hepatic (to 6-desmethylnaproxen)
Biological half-life	12-17 hours (adults)
Excretion	Renal
Identifiers
IUPAC name (+)-(S)-2-(6-Methoxynaphthalen-2-yl)propanoic acid
CAS Number	22204-53-1 Y
PubChem CID	156391
DrugBank	DB00788 Y
ChemSpider	137720 Y
UNII	57Y76R9ATQ
KEGG	D00118 Y
ChEBI	CHEBI:7476 Y
ChEMBL	CHEMBL154 Y
ECHA InfoCard	100.040.747
Chemical and physical data
Formula	C14H14O3
Molar mass	230.259 g/mol
3D model (JSmol)	Interactive image
Melting point	152–154 °C (306–309 °F)
SMILES C[C@@H](C1=CC2=C(C=C1)C=C(C=C2)OC)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 Y Key:CMWTZPSULFXXJA-VIFPVBQESA-N Y

Naproxen (brand names: Aleve, Naprosyn, and many others) is a nonsteroidal anti-inflammatory drug (NSAID) of the propionic acid class (the same class as ibuprofen) that relieves pain, fever, swelling, and stiffness. It is a nonselective COX inhibitor, usually sold as the sodium salt.

Naproxen poses an intermediate risk of stomach ulcers compared with ibuprofen, which is low-risk, and indometacin, which is high-risk. To reduce stomach ulceration risk, it is often combined with a proton-pump inhibitor (a medication that reduces stomach acid production) during long-term treatment of those with pre-existing stomach ulcers or a history of developing stomach ulcers while on NSAIDs.

Naproxen's medical uses are related to its mechanism of action as an anti-inflammatory compound. Naproxen is used to treat a variety of inflammatory conditions and symptoms that are due to excessive inflammation, such as pain and fever (naproxen has fever-reducing, or antipyretic, properties in addition to its anti-inflammatory activity). Notably, not all medications that reduce fever are anti-inflammatory compounds (such as paracetamol). Inflammatory sources of pain that may respond to naproxen's anti-inflammatory activity are conditions such as migraine, osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis and bursitis. It is also used to treat primary dysmenorrhea.