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QuickView for Naproxen (compound)

Summary
General Info

PubChem

PubChem Compound 10263296

PubChem Compound 10263296

Name:	Naproxen
PubChem Compound ID:	10263296
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.
Molecular formula:	C₁₄H₁₄O₃
Molecular weight:	231.265 g/mol

DrugBank

Identification

Name:	Naproxen
Name (isomeric):	DB00788
Drug Type:	small molecule
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.
Brand:	Reuxen, Nycopren, Floginax, Laser, Diocodal, Naprosyne, Proxen, Veradol, Napren, Xenar, Prexan, Laraflex, Naprelan, Naprosine, DL-Naproxen, Bonyl, Equiproxen, Naprius, Pranoxen, DL Naproxen, Proxine, Aleve, Naproxen Sodium, Panoxen, Ec-naprosyn, Naxen, Naprosyn, Anaprox, Naixan, Naxyn, Dysmenalgit, Niaxan, Mnpa, Naprium, Naprux
Category:	Cyclooxygenase Inhibitors, Gout Suppressants
CAS number:	22204-53-1

Pharmacology

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.
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 cyclooxygen... show more » 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. show less «
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.
Protein binding:	At therapeutic levels naproxen is greater than 99% albumin-bound.
Biotransformation:	Naproxen is extensively metabolized to 6-0-desmethyl naproxen and both parent and metabolites do not induce metabolizing enzymes.
Half Life:	The observed terminal elimination half-life is approximately 15 hours.
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

Interactions

Food interaction:

Avoid alcohol.

Take with a full glass of water.

Take with food.

Drug interaction:

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.
Timolol	The NSAID, Naproxen, may antagonize the antihypertensive effect of Timolol.
Anisindione	The NSAID, naproxen, may increase the anticoagulant effect of anisindione.
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.

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.
Timolol	The NSAID, Naproxen, may antagonize the antihypertensive effect of Timolol.
Anisindione	The NSAID, naproxen, may increase the anticoagulant effect of anisindione.
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.
Dicumarol	The NSAID, naproxen, may increase the anticoagulant effect of dicumarol.
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.
Vilazodone	Increased risk of bleeding with concomitant use of NSAIDs with vilazodone.
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.
Acenocoumarol	The NSAID, naproxen, may increase the anticoagulant effect of acenocoumarol.
Methotrexate	The NSAID, naproxen, may decrease the renal excretion of methotrexate. Increased risk of methotrexate toxicity.
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.
Ginkgo biloba	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Alendronate	Increased risk of gastric toxicity
Lithium	The NSAID, naproxen, may decrease the renal excretion of lithium. Increased risk of lithium toxicity.
Cyclosporine	Monitor for nephrotoxicity

Targets

Prostaglandin G/H synthase 2

Prostaglandin G/H synthase 1

Enzymes

Cytochrome P450 2C9

Cytochrome P450 1A2

Cytochrome P450 2C8

UDP-glucuronosyltransferase 1-1

UDP-glucuronosyltransferase 2B7

Transporters

Solute carrier organic anion transporter family member 1A2

Solute carrier family 22 member 6

Carriers