Drug/Small Molecule:
naproxen

2D structure

Overview

Trade Names: Aleve; Anaprox; Bonyl; DL Naproxen; DL-Naproxen; Diocodal; Dysmenalgit; Ec-naprosyn; Equiproxen; Floginax; Laraflex; Laser; Mnpa; Naixan; Naprelan; Napren; Naprium; Naprius; Naprosine; Naprosyn; Naprosyne; Naproxen Sodium; Naprux; Naxen; Naxyn; Niaxan; Nycopren; Panoxen; Pranoxen; Prexan; Proxen; Proxine; Reuxen; Veradol; Xenar
PharmGKB Accession Id: PA450595

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 (source: Drug Bank)

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. (source: Drug Bank)

ATC Therapeutic Categories

  • G02CC:Antiinflammatory products for vaginal administration
  • M01AE:Propionic acid derivatives
  • M02AA:Antiinflammatory preparations, non-steroids for topical use

Pharmacology, Interactions, and Contraindications

Mechanism Of Action

The mechanism of action of naproxen, like that of other NSAIDs, is believed to be associated with the inhibition of cyclooxygenase activity. Two unique cyclooxygenases have been described in mammals. The constitutive cyclooxygenase, COX-1, synthesizes prostaglandins necessary for normal gastrointestinal and renal function. The inducible cyclooxygenase, COX-2, generates prostaglandins involved in inflammation. Inhibition of COX-1 is thought to be associated with gastrointestinal and renal toxicity while inhibition of COX-2 provides anti-inflammatory activity. (source: Drug Bank)

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. (source: Drug Bank)

Food Interactions

Avoid alcohol.
Take with a full glass of water.
Take with food. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Naproxen is extensively metabolized to 6-0-desmethyl naproxen and both parent and metabolites do not induce metabolizing enzymes. (source: Drug Bank)

Protein Binding

At therapeutic levels naproxen is greater than 99% albumin-bound. (source: Drug Bank)

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. (source: Drug Bank)

Toxicity

ORAL (LD<sub>50</sub>): Acute: 248 mg/kg Rat. 360 mg/kg Mouse. Symptoms of overdose include drowsiness, heartburn, indigestion, nausea, and vomiting. (source: Drug Bank)

Isomeric SMILES Code:

C[C@@H](c1ccc2cc(ccc2c1)OC)C(=O)O (source: Drug Bank)

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
No phenotype data Genotype Data Available Literature annotations available Not annotated
CYP1A2
  •   
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  • PK
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Publications
Phenotype data available Genotype Data Available Literature annotations available Not annotated
CYP2C8
  •   
  •   
  • PK
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  •   
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP2C9
  • CO
  •   
  • PK
  •   
  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Not annotated
UGT1A6
  •   
  •   
  • PK
  •   
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Publications

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Gene Description
PTGS1 Uncurated Annotation (source: Drug Bank)
PTGS2 Uncurated Annotation (source: Drug Bank)

PharmGKB Curated Pathways

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

Drug Description
acenocoumarol Uncurated Annotation The NSAID increases the anticoagulant effect (source: Drug Bank)
alendronate Uncurated Annotation Increased risk of gastric toxicity (source: Drug Bank)
cyclosporine Uncurated Annotation Monitor for nephrotoxicity (source: Drug Bank)
dicumarol Uncurated Annotation The NSAID increases the anticoagulant effect (source: Drug Bank)
lithium Uncurated Annotation The NSAID increases serum levels of lithium (source: Drug Bank)
methotrexate Uncurated Annotation The NSAID increases the effect and toxicity of methotrexate (source: Drug Bank)
warfarin Uncurated Annotation The NSAID increases the anticoagulant effect (source: Drug Bank)

Curated Information

The following diseases are in curated knowledge about this drug.

  Disease Relationship Evidence
No phenotype data No genotype data Literature annotations available Not annotated
Hemorrhage
  • CO
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  •   
  •   
  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Not annotated
Myocardial Infarction
  •   
  • PD
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  •   
  •   
Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Curated Phenotype Datasets

These datasets are sorted alphabetically by title.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

  1. The Connectivity Map: using gene-expression signatures to connect small molecules, genes, and disease

Downloads

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LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00788
KEGG Compound ID:
C01517
KEGG Drug ID:
D00118
PubChem Compound ID:
1302
PubChem Substance ID:
4682

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

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