File:Naproxen2DACS.svg · Wikimedia Commons · See Wikimedia Commons
naproxen
Sign in to saveAlso known as (S)-naproxen, 2-(6-methoxy-2-naphthyl)propionic acid, (+)-2-(methoxy-2-naphthyl)-propionsäure, (+)-(S)-6-methoxy-α-methyl-2-naphthaleneacetic acid, (S)-2-(6-methoxy-2-naphthyl)propionic acid, (S)-(+)-2-(6-methoxy-2-naphthyl)propionic acid, (S)-6-methoxy-alpha-methyl-2-naphthaleneacetic acid, (S)-2-(6-methoxy-2-naphthyl)propanoic acid
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.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 464372587
- Drug.image
- Naproxen2DACS.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200
- Drug.image2
- (S)-naproxen-from-xtal-3D-bs-17.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Aleve, Naprosyn, others
- Drug.MedlinePlus
- a681029
- Drug.DailyMedID
- Naproxen
- Drug.pregnancy_AU
- C
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- G02
- Drug.ATC_suffix
- CC02
- Drug.ATC_supplemental
- , , ,
- Drug.legal_AU
- S2
- Drug.legal_AU_comment
- when in preparations that contain no more than 15 days' supply. Otherwise it is Schedule 4 (Prescription only).
- Drug.legal_CA
- OTC / Rx-only
via Wikipedia infobox
Chemical data
- Formula
- C14H14O3
- Molecular weight
- 230.26 g/mol
- IUPAC name
- (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
- SMILES
- C[C@@H](C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)O
- InChIKey
- CMWTZPSULFXXJA-VIFPVBQESA-N
- XLogP
- 3.3
- Polar surface area
- 46.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
8,350 papers- Clinical pharmacokinetics of naproxen.Clinical pharmacokinetics · 1997
- Recent Advances in the Synthesis of Ibuprofen and Naproxen.Molecules (Basel, Switzerland) · 2021
- Naproxen sodium.Journal of the American Pharmaceutical Association (Washington, D.C. : 1996) · 1996
- Naproxen in the environment: its occurrence, toxicity to nontarget organisms and biodegradation.Applied microbiology and biotechnology · 2020
- Simultaneous separation of naproxen and 6-O-desmethylnaproxen metabolite in saliva samples by liquid chromatography-tandem mass spectrometry: Pharmacokinetic study of naproxen alone and associated with esomeprazol-Results.PloS one · 2022
via PubMed
Wikidata facts
- Mass
- 230.094
Show 8 more facts
- chemical formula
- C₁₄H₁₄O₃
- Commons category
- Naproxen
- canonical SMILES
- CC(C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)O
- isomeric SMILES
- C[C@@H](C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)O
- World Health Organisation international non-proprietary name
- naproxen
- MCN code
- 2918.99.40
- melting point
- 155
- start time
- 1976-00-00
Sources (6)
via Wikidata · CC0
~13 min read
Article
22 sectionsContents
- Medical uses
- Available formulations
- Pregnancy and lactation
- Adverse effects
- Gastrointestinal
- Cardiovascular
- Drug-drug interactions
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Pharmacogenetics
- Chemistry
- Synthesis
- Society and culture
- Brand names
- Access restrictions
- Ecological effects
- Research
- Veterinary use
- Horses
- References
- External links
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.