Naproxen
- Atc Codes:G02CC02#M01AE02#M02AA12
- CAS Codes:22204-53-1#26159-34-2
- PHARMGKB ID:22204-53-1#26159-34-2
Table of contents
- Brand Names
- Drug Combinations
- Chemistry
- Pharmacologic Category
- Mechanism of Action
- Therapeutic Use
- Pregnancy and Lactation Implications
- Contraindications
- Warnings and Precautions
- Adverse Reactions
- Caution and personalized dose adjustment in patients with the following genotypes
- Other genes that may be involved
- Substrate of
- Inhibits
- Drug Interactions
- Nutrition/Nutraceutical Interactions
- Dosage
- Pharmacokinetics and Pharmacodynamics
- Special Considerations
Brand Names
Europe
Austria: Naprobene, Naproxen, Proxen; Belgium: Aleve, Apranax, Naproflam, Naprosyne, Naproxen, Naproxene; Bulgaria: Momendol, Nalgesin, Naproxen; Cyprus: Naprorex, Priaxen; Czech Republic: Aleve, Emoxen, Nalgesin S; Denmark: Bonyl, Naproxen; Estonia: Nalgesin S, Naxenol; Finland: Alpoxen, Eox, Miranax, Naprometin, Napromex, Naproxen, Pronaxen; France: Aleve, Apranax, Naprosyne, Naproxene; Germany: Alacetan NNA, Aleve, Dolorsan Femina, Dysmenalgit, Momendol, Naprocutan, Naproxen, Proxen; Greece: Anaprox, Naprosyn; Hungary: Aleve, Apranax, Napmel; Ireland: Genoxen, Gerinap E.C., Momendol, Naprosyn; Italy: Akudol, Aleve, Dropsen, Floginax, Gynestrel, Laser R, Momendol, Napreben, Naprius, Naprocet, Naprossene, Naprosyn, Naproxen, Naproxene, Neoeblimon, Nitens, Prexan, Proxagol, Synflex, Uninapro, Xenar; Latvia: Aleve, Emox; Lithuania: Aleve, Emox, Momendol, Nalgesin S; Malta: Momendol, Naprorex, Naprosyn, Naproxen, Priaxen; Netherlands: Aleve, Naprelan, Naprovite, Naproxen; Poland: Aleve, Anapran, Apo-Napro, Apranax, Boloxen, Naprosyn, Naproxen, Tarproxen, Vero; Portugal: Naprocet, Momendol, Naprosyn, Naproxeno, Reuxen; Romania: Aleve, Momendol, Reuxen; Slovakia: Aleve, Emoxen, Nalgesin S, Napsyn; Slovenia: Nalgesin, Naprosyn; Spain: Aleve, Anaprox, Antalgin, Lundiran, Naprosyn, Naproxeno; Sweden: Alpoxen, Eox, Naprosyn, Naproxen, Pronaxen; UK: Feminax Ultra, Naprosyn, Naproxen, Synflex.
North America
Canada: Aleve, Anaprox, Apo-Napro-Na, Naprelan, Naprosyn, Naproxen, Novo-Naprox, Nu Naprox; USA: Aleve, Anaprox, Naprelan, Naprosyn.
Latin America
Argentina: Alidase, Bumaflex N-S, Congex 24, Debril, Fabralgina, Melgar, Mox 12 HS, Naprogen, Naprontag, Naproxeno, Naprux, Tundra; Brazil: Flanax-Bayer, Napronax, Naprosyn, Naprox, Naproxeno; Mexico: Actiquim, Analgen, Arsenal, Arxen, Bioxan, Bixen, Dafloxen, Diferbest, Dolxen, Donaprox, Edem, Fagofen, Faraxen, Flanax-Bayer, Flavoxen, Flaxendol, Flogen, Fuxen, Inflanox, Iqfasol, Luzapren, Messelxen, Naflapen, Napoxol, Naproxen, Naproxeno, Naxen, Naxopaar, Neonaxil, Novaxen, Pactens-Merck, Praxedol, Profaxen, Pronat, Pronaxil, Pronoxen, Propional, Proxalin, Sertrixen, Sodixen, Tandax, Tanizona, Velsay.
Asia
Japan: Naixan.
Drug combinations
Naproxen and Carisprodol
Naproxen and Esomeprazole
Naproxen and Lansoprazole
Naproxen and Misoprostol
Naproxen and Pseudoephedrine
Naproxen and Sumatriptan
Naproxen and Tetracycline
Chemistry
Naproxen: C~14~H~14~O~3~. Mw: 230.26. (+)-(S)-6-Methoxy-α-methyl-2-naphthaleneacetic acid. CAS-22204-53-1 (1970).
Naproxen Sodium: C~14~H~13~NaO~3~. Mw: 252.24. 2-Naphthaleneacetic acid, 6-methoxy-α-methyl-, sodium salt, (S). CAS-26159-34-2 (1973).
Pharmacologic Category
Analgesics and Antipyretics; Other Nonsteroidal Anti-inflammatory Agents. Antigout Agents. (ATC-Code: G02CC02; M01AE02; M02AA12).
Mechanism of action
Inhibits prostaglandin synthesis by decreasing activity of enzyme cyclooxygenase (COX-1/PTGS1 and COX-2/PTGS2), which results in decreased formation of prostaglandin precursors. Exhibits anti-inflammatory, analgesic, and antipyretic activity.
Therapeutic use
Management of ankylosing spondylitis, osteoarthritis, and rheumatoid disorders (including juvenile rheumatoid arthritis in children ≥2 years of age), acute gout, mild-to-moderate pain, tendonitis, bursitis, dysmenorrhea, fever in children ≥12 years of age and adults.
Pregnancy and lactiation implications
Use should be avoided in 3^rd^ trimester (possible premature closure of ductus arteriosus). Not recommended in nursing women.
Unlabeled use
Contraindications
Hypersensitivity to naproxen, aspirin, other NSAIDs, or any component of the formulation. Perioperative pain in setting of coronary artery bypass graft surgery.
Warnings and precautions
Even in patients without prior exposure, anaphylactoid reactions may occur (patients with «aspirin triad» (bronchial asthma, aspirin intolerance, rhinitis) may be at increased risk). Do not use in patients who experience bronchospasm, asthma, rhinitis, or urticaria with NSAID or aspirin therapy. May increase risk of aseptic meningitis, especially in systemic lupus erythematosus and mixed connective tissue disorders. Platelet adhesion and aggregation may be decreased (may prolong bleeding time). Anemia may occur. NSAIDs associated with increased risk of adverse cardiovascular events, including MI, stroke, and new onset or worsening of pre-existing hypertension. Risk may be increased with duration of use or pre-existing cardiovascular risk factors or disease (use caution with fluid retention, heart failure, or hypertension). Concurrent administration of ibuprofen, and potentially other nonselective NSAIDs, may interfere with aspirin’s cardioprotective effect. NSAIDs may increase risk of gastrointestinal irritation, inflammation, ulceration, bleeding, and perforation (use caution with history of GI disease (bleeding or ulcers), concurrent therapy with aspirin, anticoagulants and/or corticosteroids, smoking, use of alcohol, elderly or debilitated patients). NSAIDs may cause serious skin adverse events including exfoliative dermatitis, Stevens-Johnson syndrome, and toxic epidermal necrolysis. Use contraindicated for treatment of perioperative pain in setting of coronary artery bypass graft surgery. Risk of MI and stroke may be increased with use following coronary artery bypass graft surgery. Use with caution in decreased hepatic function (rarely severe hepatic reactions occurred with NSAID use). NSAID use may compromise existing renal function (patients with impaired renal function, dehydration, heart failure, liver dysfunction, those taking diuretics, and ACEIs, and the elderly are at greater risk of renal toxicity). Not recommended for use in advanced renal disease. Long-term NSAID use may result in renal papillary necrosis. The elderly are at increased risk for adverse effects (especially peptic ulceration, CNS effects, renal toxicity) from NSAIDs even at low doses. Not for self-medication in children <12 years of age. Consuming ≥3 alcoholic beverages/day or taking longer than recommended may increase risk of GI bleeding. Withhold prior to surgical or dental procedures.