Naproxen

• Catalog No.: DB00788
• CAS Number: 22204-53-1
• M. F.: C14H14O3
• M. W.: 230.25916

SYNONYMS

• IUPAC name: 2-(6-methoxynaphthalen-2-yl)propanoic acid
• IUPAC Traditional name: naprosyn
• Brand Name: Napren; Nycopren; Panoxen; Naprosyne; Naixan; DL Naproxen; Aleve; Anaprox; Bonyl; Dysmenalgit; Ec-naprosyn; Floginax; Naprosine; Naprux; Naxen; Naxyn; Pranoxen; Reuxen; DL-Naproxen; Diocodal; Equiproxen; Laraflex; Laser; Mnpa; Naprelan; Naprium; Naprius; Naprosyn; Naproxen Sodium; Niaxan; Prexan; Proxen; Proxine; Veradol; Xenar

DATABASE IDS

• CAS Number: 22204-53-1

PROPERTIES

• Hydrophobicity(logP): 2.8
• Solubility: 15.9 mg/L

DETAILS

Description (English)

• Drug Groups: approved
• Description: An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout. [PubChem]
• Indication: For the treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, tendinitis, bursitis, and acute gout. Also for the relief of mild to moderate pain and the treatment of primary dysmenorrhea.
• Pharmacology: Naproxen is a member of the arylacetic acid group of nonsteroidal anti-inflammatory drugs (NSAIDs). Naproxen has analgesic and antipyretic properties. As with other NSAIDs, its mode of action is not fully understood; however, its ability to inhibit prostaglandin synthesis may be involved in the anti-inflammatory effect.
• Toxicity: ORAL (LD₅₀): Acute: 248 mg/kg [Rat]. 360 mg/kg [Mouse]. Symptoms of overdose include drowsiness, heartburn, indigestion, nausea, and vomiting.
• Affected Organisms: Humans and other mammals
• Biotransformation: Naproxen is extensively metabolized to 6-0-desmethyl naproxen and both parent and metabolites do not induce metabolizing enzymes.
• Absorption: Naproxen itself is rapidly and completely absorbed from the GI tract with an in vivo bioavailability of 95%. Although naproxen itself is well absorbed, the sodium salt form is more rapidly absorbed resulting in higher peak plasma levels for a given dose. Food causes a slight decrease in the rate absorption.
• Half Life: The observed terminal elimination half-life is approximately 15 hours.
• Protein Binding: At therapeutic levels naproxen is greater than 99% albumin-bound.
• References: Kearney PM, Baigent C, Godwin J, Halls H, Emberson JR, Patrono C: Do selective cyclo-oxygenase-2 inhibitors and traditional non-steroidal anti-inflammatory drugs increase the risk of atherothrombosis? Meta-analysis of randomised trials. BMJ. 2006 Jun 3;332(7553):1302-8. [Pubmed] ; Zhang J, Ding EL, Song Y: Adverse effects of cyclooxygenase 2 inhibitors on renal and arrhythmia events: meta-analysis of randomized trials. JAMA. 2006 Oct 4;296(13):1619-32. Epub 2006 Sep 12. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

REFERENCES

• Kearney PM, Baigent C, Godwin J, Halls H, Emberson JR, Patrono C: Do selective cyclo-oxygenase-2 inhibitors and traditional non-steroidal anti-inflammatory drugs increase the risk of atherothrombosis? Meta-analysis of randomised trials. BMJ. 2006 Jun 3;332(7553):1302-8. Pubmed
• Zhang J, Ding EL, Song Y: Adverse effects of cyclooxygenase 2 inhibitors on renal and arrhythmia events: meta-analysis of randomized trials. JAMA. 2006 Oct 4;296(13):1619-32. Epub 2006 Sep 12. Pubmed