Naproxen

Naproxen

Clinical data
Pronunciation	/nəˈprɒksən/
Trade names	Aleve, Anaprox, Apronax, Naprelan, Naprosyn, Flanax(Belmora USA)
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) CA: OTC UK: Pharmacy medicines US: OTC In Australia it is only Schedule 2 in preparations that contain no more than 15 days' supply. Otherwise it is schedule 4 (prescription-only).
Pharmacokinetic data
Bioavailability	95% (oral)
Protein binding	99%
Metabolism	Hepatic (to 6-desmethylnaproxen)
Biological half-life	12–24 hours
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 Y
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 (Jmol)	Interactive image
Melting point	152–154 °C (306–309 °F)
SMILES C[C@@H](c1ccc2cc(ccc2c1)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,Flanax(Belmora) 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 to 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 is commonly used to reduce pain, fever, inflammation, and stiffness caused by 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.

Naproxen has been used to differentiate between infectious fevers and neoplastic or connective tissue disease-related fevers.