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.
OverviewAI-generated
Naproxen is a chemical compound with the formula C₁₄H₁₄O₃. Its IUPAC name is (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid. The substance has a mass of 230.094 and a melting point of 155. It carries a charge of 0 and features one hydrogen bond donor and three hydrogen bond acceptors. The xlogp value is 3.3, while the topological polar surface area is 46.5.
The compound was introduced in 1976. It is associated with an MCN code of 2918.99.40. Naproxen has been the subject of 8350 publications indexed in PubMed. Additionally, it is referenced by 688 other encyclopedia articles.
Synthesized by Vinony from 21 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
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
~13 min read
Encyclopedic overview
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.
Excerpted from Wikipedia’s “naproxen” article, available under the CC BY-SA 4.0 licence.