Naproxen /nəˈprɒksən/ (INN; brand names: Aleve, Naprosyn and many others) is a nonselective COX inhibitor; usually sold as the sodium salt, naproxen is a nonsteroidal anti-inflammatory drug (NSAID) of the propionic acid class (which puts it in the same class as ibuprofen) commonly used for relief of a wide variety of pain, fever, swelling and stiffness.[2][3]:665,673
Starting at
(+)-(S)-2-(6-methoxynaphthalen-2-yl) propanoic acid |
Trade names | Aleve, Anaprox, Apronax, Naprelan, Naprosyn |
AHFS/Drugs.com | monograph |
MedlinePlus | a681029 |
Licence data | US Daily Med:link |
Pregnancy category |
AU: C US: C (Risk not ruled out) |
Legal status |
AU: S2 (Pharmacy only) CA: OTC UK: Pharmacy medicines US: OTC In Australia it is only Schedule 2 when in preparations containing no more than 15 days’ supply. Otherwise it is schedule 4 (prescription-only).[1] |
Routes of administration |
Oral. |
Bioavailability | 95% (oral) |
Protein binding | 99% |
Metabolism | Hepatic (to 6-desmethylnaproxen) |
Biological half-life | 12–24 hours |
Excretion | Renal |
CAS Number | 22204-53-1 |
ATC code | G02CC02 M01AE02, M02AA12 |
PubChem | CID: 156391 |
DrugBank | DB00788 |
ChemSpider | 137720 |
UNII | 57Y76R9ATQ |
KEGG | D00118 |
ChEBI | CHEBI:7476 |
ChEMBL | CHEMBL154 |
Formula | C14H14O3 |
Molecular mass | 230.259 g/mol |
SMILES[show] |
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InChI[show] |
Melting point | 152–154 °C (306–309 °F) |