Aleve;Anaprox;Bonyl;Diocodal;DL Naproxen;DL-Naproxen;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;

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]

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Synthesis Reference

Not Available

General Reference

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

Type	small molecule

Classes

Not Available

Substructures

Not Available

ANTIINFLAMMATORY AND ANTIRHEUMATIC 消炎抗风湿;

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.
Pharmacodynamics	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.
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.
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.
Volume of distribution	Not Available
Protein binding	At therapeutic levels naproxen is greater than 99% albumin-bound.
Metabolism	Naproxen is extensively metabolized to 6-0-desmethyl naproxen and both parent and metabolites do not induce metabolizing enzymes. Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us. Substrate Enzymes Product Naproxen Cytochrome P450 2C9 Cytochrome P450 2C8 Cytochrome P450 1A2 O-Desmethylnaproxen Details Naproxen UDP-glucuronosyltransferase 1-1 UDP-glucuronosyltransferase 2B7 Naproxen O-glucuronide Details
Route of elimination	Not Available
Half life	The observed terminal elimination half-life is approximately 15 hours.
Clearance	Not Available
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
Pathways	Pathway Name SMPDB ID Naproxen Pathway SMP00120

Properties
State	solid
Experimental Properties	Property Value Source melting point 153 °C PhysProp water solubility 15.9 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 3.18 HANSCH,C ET AL. (1995) logS -4.16 ADME Research, USCD Caco2 permeability -4.83 ADME Research, USCD pKa 4.15 SANGSTER (1994)
Predicted Properties	Property Value Source water solubility 5.11e-02 g/l ALOGPS logP 3.29 ALOGPS logP 2.99 ChemAxon logS -3.6 ALOGPS pKa (strongest acidic) 4.19 ChemAxon pKa (strongest basic) -4.8 ChemAxon physiological charge -1 ChemAxon hydrogen acceptor count 3 ChemAxon hydrogen donor count 1 ChemAxon polar surface area 46.53 ChemAxon rotatable bond count 3 ChemAxon refractivity 64.85 ChemAxon polarizability 24.81 ChemAxon

Drug	Interaction
Acenocoumarol	The NSAID, naproxen, may increase the anticoagulant effect of acenocoumarol.
Alendronate	Increased risk of gastric toxicity
Anisindione	The NSAID, naproxen, may increase the anticoagulant effect of anisindione.
Apixaban	Due to pharmacodynamic interaction, a 50-60% increase in anti-Factor Xa activity may be observed with concomitant therapy.
Azilsartan medoxomil	Increases toxicity of each. May deteriorate renal function, particularly in volume depleted or elderly patients. Decreases effects of azilsartan by antagonism.
Colesevelam	Bile acid sequestrants may decrease the absorption of Nonsteroidal Anti-Inflammatory Agents. Monitor for decreased serum concentrations/therapeutic effects of nonsteroidal anti-inflammatory agents (NSAID) if coadministered with bile acid sequestrants. Separating the administration of doses by 2 or more hours may reduce (but not eliminate) the risk of interaction. The manufacturer of colesevelam recommends that drugs should be administered at least 1 hour before or 4 hours after colesevelam.
Cyclosporine	Monitor for nephrotoxicity
Dicumarol	The NSAID, naproxen, may increase the anticoagulant effect of dicumarol.
Ginkgo biloba	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Lithium	The NSAID, naproxen, may decrease the renal excretion of lithium. Increased risk of lithium toxicity.
Methotrexate	The NSAID, naproxen, may decrease the renal excretion of methotrexate. Increased risk of methotrexate toxicity.
Pralatrexate	NSAIDs increase the risk of toxicity due to impairment of renal clearance of pralatrexate thus increasing exposure. Monitor for adverse effects or adjust dose of pralatrexate.
Tapentadol	Increases the AUC of tapentadol by 17%. These changes are not considered clinically relevant and no change in dose is required.
Telmisartan	Concomitant use of Telmisartan and Naproxen may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Timolol	The NSAID, Naproxen, may antagonize the antihypertensive effect of Timolol.
Trandolapril	The NSAID, Naproxen, may reduce the antihypertensive effect of Trandolapril. Consider alternate therapy or monitor for changes in Trandolapril efficacy if Naproxen is initiated, discontinued or dose changed.
Treprostinil	The prostacyclin analogue, Treprostinil, may increase the risk of bleeding when combined with the NSAID, Naproxen. Monitor for increased bleeding during concomitant thearpy.
Triflusal	The metabolite of triflusal, 2-hydroxy-4-trifluoro-methyl-benzoic acid (HTB), impairs the serum protein binding of naproxen to the same extent as acetylsalisylic acid. Thus, the free fraction of glisentide may be increased. A dosage reduction may be required if used in combination.
Vilazodone	Increased risk of bleeding with concomitant use of NSAIDs with vilazodone.
Warfarin	The antiplatelet effects of naproxen may increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for signs and symptoms of bleeding during concomitant therapy.

• Avoid alcohol.
• Take with a full glass of water.
• Take with food.