naproxen

A drug, C₁₄H₁₄O₃, used to reduce inflammation and pain, especially in the treatment of arthritis.

[Shortening and alteration of methoxynaphthylpropionic acid, one of its chemical names.]

Brand names: Aflaxen™Aleve®Anaprox®Anaprox® DSMediproxen®Naprelan®Naprelan® 375Naprelan® 500Naprosyn®Wal-Proxen

Chemical formula:

Drug Forms:
• Naproxen Gastro-resistant tablet (below)
• Naproxen Oral tablet
• Naproxen Sodium Oral tablet
• Naproxen Sodium Oral tablet, extended-release
• Naproxen Oral suspension
• Naproxen Oral tablet, biphasic release

Español:
• Naproxeno, Tabletas gastrorresistentes
• Naproxeno, Tableta oral
• Naproxeno Sódico, Tableta oral
• Naproxeno Sódico, Tableta oral de liberación prolongada
• Naproxeno, Suspensión oral
• Naproxeno, Tableta oral de liberación bifásica

Naproxen Gastro-resistant tablet

What is this medicine?

NAPROXEN (na PROX en) is a non-steroidal anti-inflammatory drug (NSAID). It is used to reduce swelling and to treat pain. This medicine may be used for dental pain, headache, or painful monthly periods. It is also used for painful joint and muscular problems such as arthritis, tendinitis, bursitis, and gout.
 
This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.

What should I tell my health care provider before I take this medicine?

They need to know if you have any of these conditions:
• asthma
• cigarette smoker
• drink more than 3 alcohol containing drinks a day
• heart disease or circulation problems such as heart failure or leg edema (fluid retention)
• high blood pressure
• kidney disease
• liver disease
• stomach bleeding or ulcers
• an unusual or allergic reaction to naproxen, aspirin, other NSAIDs, other medicines, foods, dyes, or preservatives
• pregnant or trying to get pregnant
• breast-feeding

How should I use this medicine?

Take this medicine by mouth with a glass of water. Follow the directions on the prescription label. Do not cut, crush or chew this medicine. Take it with food if your stomach gets upset. Try to not lie down for at least 10 minutes after you take it. Take your medicine at regular intervals. Do not take your medicine more often than directed. Long-term, continuous use may increase the risk of heart attack or stroke.

A special MedGuide will be given to you by the pharmacist with each prescription and refill. Be sure to read this information carefully each time.

Talk to your pediatrician regarding the use of this medicine in children. Special care may be needed.

Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.

What may interact with this medicine?

• alcohol
• antacids
• aspirin
• cidofovir
• diuretics
• lithium
• medicines for stomach, or intestine problems, like acid reflux or GERD
• methotrexate
• other drugs for inflammation like ketorolac or prednisone
• pemetrexed
• probenecid
• sucralfate
• warfarin

This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.

What should I watch for while using this medicine?

Tell your doctor or health care professional if your pain does not get better. Talk to your doctor before taking another medicine for pain. Do not treat yourself.

This medicine does not prevent heart attack or stroke. In fact, this medicine may increase the chance of a heart attack or stroke. The chance may increase with longer use of this medicine and in people who have heart disease. If you take aspirin to prevent heart attack or stroke, talk with your doctor or health care professional.

Do not take ibuprofen with this medicine. Side effects such as stomach upset, nausea, or ulcers may be more likely to occur. Many medicines available without a prescription should not be taken with this medicine.

This medicine can cause ulcers and bleeding in the stomach and intestines at any time during treatment. Do not smoke cigarettes or drink alcohol. These increase irritation to your stomach and can make it more susceptible to damage from this medicine. Ulcers and bleeding can happen without warning symptoms and can cause death.

You may get drowsy or dizzy. Do not drive, use machinery, or do anything that needs mental alertness until you know how this medicine affects you. Do not stand or sit up quickly, especially if you are an older patient. This reduces the risk of dizzy or fainting spells.

This medicine can cause you to bleed more easily. Try to avoid damage to your teeth and gums when you brush or floss your teeth.

What side effects may I notice from receiving this medicine?

Side effects that you should report to your doctor or health care professional as soon as possible:
• black or bloody stools, blood in the urine or vomit
• blurred vision
• chest pain
• difficulty breathing or wheezing
• nausea or vomiting
• skin rash, skin redness, blistering or peeling skin, hives, or itching
• slurred speech or weakness on one side of the body
• swelling of eyelids, throat, lips
• unexplained weight gain or swelling
• unusually weak or tired
• yellowing of eyes or skin

Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
• constipation
• headache
• heartburn

This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.

Where should I keep my medicine?

Keep out of the reach of children.

Store at room temperature between 15 and 30 degrees C (59 and 86 degrees F). Keep container tightly closed. Throw away any unused medicine after the expiration date.

Last updated: 7/1/2002

Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.

A non-steroidal anti-inflammatory drug used to treat chronic inflammatory conditions, such as arthritis. Its use for treating soft-tissue sports injuries has been advocated.

A propionic acid derivative with analgesic, antipyretic and anti-inflammatory activity (a nonsteroidal anti-inflammatory agent); its use is associated with gastroduodenal ulceration in dogs.

Naproxen
Systematic (IUPAC) name
(+)-(S)-2-(6-methoxynaphthalen-2-yl) propanoic acid
Identifiers
CAS number	22204-53-1
ATC code	G02CC02 M01AE02, M02AA12
PubChem	1302
DrugBank	APRD01135
ChemSpider	137720
Chemical data
Formula	C14H14O3
Mol. mass	230.259 g/mol
Pharmacokinetic data
Bioavailability	95% (oral)
Protein binding	99%
Metabolism	Hepatic (to 6-desmethylnaproxen)
Half life	12–24 hours
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	C(AU) B(US)
Legal status	Pharmacy Only (S2)(AU) P(UK) OTC(US) OTC(Ca)
Routes	Oral
Y(what is this?)  (verify)

Naproxen Sodium (INN) (pronounced /nəˈprɒksən/) is a non-steroidal anti-inflammatory drug (N-SAID) commonly used for the reduction of mild to moderate pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes. Naproxen and naproxen sodium are marketed under various trade names including: Aleve, Anaprox, Antalgin, Feminax Ultra, Flanax, Inza, Miranax, Naprelan, Naprogesic, Naprosyn, Narocin, Proxen, Synflex, Xenobid.

Naproxen was originally marketed as the prescription drug Naprosyn in 1976, and naproxen sodium was first marketed under the trade name Anaprox in 1980. It remains a prescription-only drug in much of the world. The U.S. Food and Drug Administration (FDA) approved the use of naproxen sodium as an over-the-counter (OTC) drug in 1994, where OTC preparations are sold under the trade name Aleve. In Australia, packets of 275mg tablets of naproxen sodium are Schedule 2 Pharmacy Medicines, with a maximum daily dose of 5 tablets/1375mg. In the UK, 250 mg tablets of naproxen were approved for OTC sale under the brand name Feminax Ultra in 2008, for the treatment of primary dysmenorrhoea in women aged 15 to 50.^[1]. Aleve became available over-the-counter in most provinces in Canada on July 14, 2009 with the exception of British Columbia, Quebec and Newfoundland and Labrador.^[2]

Contents 1 Structure and details 2 Synthesis 3 Adverse effects and warnings 3.1 IP110-Naproxen link to Pseudoporphyria 3.2 Risk of heart attack or stroke 4 See also 5 References 6 External links

Structure and details

Naproxen is a member of the 2-arylpropionic acid (profen) family of NSAIDs. The free acid is an odorless, white to off-white crystalline substance. It is lipid-soluble and practically insoluble in water. It has a melting point of 153 °C.

Synthesis

Naproxen has been produced by Syntex industrially as follows:^[3]

Other synthetic routes have also been discussed.^[3]

Adverse effects and warnings

IP110 Naproxen Tablets: Like other NSAIDs, naproxen can inhibit the excretion of sodium and lithium. Extreme care must be taken by those who use this drug along with lithium supplements. Naproxen is also not recommended for use with NSAIDs of the salicylate family (Aspirin) (drugs may reduce each other's effects) or with anticoagulants (may increase risk of bleeding). Naproxen preparations containing sodium (e.g., Anaprox, Aleve, etc.) are not recommended for use in patients with sodium-sensitive hypertension, due to potential adverse effects on blood pressure in this small subset of hypertensive patients.

In August 2006, the Journal Birth Defects Research Part B^[4] published results indicating that pregnant women who take NSAIDs including naproxen in the first trimester run an increased risk of having a child with congenital birth defects, particularly heart anomalies.

IP110-Naproxen link to Pseudoporphyria

Naproxen IP110 has also been linked to cases of Pseudoporphyria, specifically in those with skin type II or lower, especially with blue or green eyes.

Risk of heart attack or stroke

This section requires expansion.

The National Institutes of Health prematurely terminated a randomized clinical trial^[5] of naproxen and celecoxib for prevention of Alzheimer's disease, after preliminary data suggested similar effects to Viagra, such as heart attack or stroke, in patients taking naproxen.

See also

• Aspirin
• Paracetamol (acetaminophen)
• Ibuprofen

References

1. ^ Pocock, Nicola (2006). "MHRA approves availability of OTC naproxen (Feminax Ultra)". NHS Press Release. http://www.druginfozone.nhs.uk/Record%20Viewing/viewRecord.aspx?id=591725. 
2. ^ http://www.bayer.ca/files/Aleve%20Release.July14.FINAL_.pdf
3. ^ ^{a b} Peter J. Harrington and Eric Lodewijk (1997). "Twenty Years of Naproxen Technology". Org. Process Res. Dev. 1 (1): 72-76. doi:10.1021/op960009e. 
4. ^ Ofori, et al. (August 2006). "Risk of congenital anomalies in pregnant users of non-steroidal anti-inflammatory drugs: a nested case-control study". Birth Defects Research Part B: Developmental and Reproductive Toxicology. http://www3.interscience.wiley.com/journal/112752202/abstract. 
5. ^ ADAPT Research Group (2006). "Cardiovascular and Cerebrovascular Events in the Randomized, Controlled Alzheimer's Disease Anti-Inflammatory Prevention Trial (ADAPT)". PLoS Clinical Trials. http://clinicaltrials.plosjournals.org/perlserv/?request=get-document&doi=10.1371/journal.pctr.0010033. 

External links

Look up naproxen in Wiktionary, the free dictionary.

• CID 1302 from PubChem
• EINECS number 244-838-7
• MedlinePlus Information on naproxen
• FDA Statement on Naproxen, released 20 December 2004
• Alzheimer's Disease Anti-Inflammatory Prevention Trial
• Forbes article (expressing the point of view that the risk of heart attack or stroke was overstated)
• Which NSAID for Heart Disease Patients? - Medscape

v • d • e Non-steroidal anti-inflammatory drug (NSAID) products (primarily M01A and M02A, also N02BA) Salicylates Aspirin (acetylsalicylic acid) · Aloxiprin · Benorylate · Diflunisal · Ethenzamide · Magnesium salicylate · Methyl salicylate · Salsalate · Salicin · Salicylamide · Sodium salicylate Arylalkanoic acids Diclofenac · Aceclofenac · Acemetacin · Alclofenac · Bromfenac · Etodolac · Indometacin · Indometacin farnesil · Nabumetone · Oxametacin · Proglumetacin · Sulindac · Tolmetin 2-Arylpropionic acids (profens) Ibuprofen · Alminoprofen · Benoxaprofen · Carprofen · Dexibuprofen · Dexketoprofen · Fenbufen · Fenoprofen · Flunoxaprofen · Flurbiprofen · Ibuproxam · Indoprofen† · Ketoprofen · Ketorolac · Loxoprofen · Miroprofen · Naproxen · Oxaprozin · Pirprofen · Suprofen · Tarenflurbil · Tiaprofenic acid N-Arylanthranilic acids (fenamic acids) Mefenamic acid · Flufenamic acid · Meclofenamic acid · Tolfenamic acid Pyrazolidine derivatives Phenylbutazone · Ampyrone · Azapropazone · Clofezone · Kebuzone · Metamizole† · Mofebutazone · Oxyphenbutazone · Phenazone · Sulfinpyrazone Oxicams Piroxicam · Droxicam · Lornoxicam · Meloxicam · Tenoxicam · Ampiroxicam COX-2 inhibitors Celecoxib · Deracoxib‡ · Etoricoxib · Firocoxib‡ · Lumiracoxib† · Parecoxib · Rofecoxib† · Valdecoxib† Sulfonanilides Nimesulide Topically used products Bendazac · Diclofenac · Etofenamate · Felbinac · Flurbiprofen · Ibuprofen · Indometacin · Ketoprofen · Naproxen · Piroxicam · Suprofen COX-inhibiting nitric oxide donators Naproxcinod Others Fluproquazone Items listed in bold indicate initially developed compounds of specific groups. †Withdrawn drugs. ‡Veterinary use medications.

v • d • e Anti-inflammatory products (M01A) Pyrazolidine/Butylpyrazolidines Ampyrone · Clofezone · Kebuzone · Metamizole · Mofebutazone · Oxyphenbutazone · Phenazone · Phenylbutazone · Sulfinpyrazone Acetic acid derivatives and related substances Aceclofenac · Acemetacin · Alclofenac · Bromfenac · Bumadizone · Bufexamac · Diclofenac · Difenpiramide · Etodolac · Fentiazac · Indometacin · Ketorolac · Lonazolac · Oxametacin · Proglumetacin · Sulindac · Tolmetin · Zomepirac Oxicams Ampiroxicam · Droxicam · Lornoxicam · Meloxicam · Piroxicam · Tenoxicam Propionic acid derivatives Alminoprofen · Benoxaprofen · Dexibuprofen · Dexketoprofen · Fenbufen · Fenoprofen · Flunoxaprofen · Flurbiprofen · Ibuprofen · Ibuproxam · Indoprofen · Ketoprofen · Naproxen · Oxaprozin · Pirprofen · Suprofen · Tiaprofenic acid Fenamates Flufenamic acid · Meclofenamic acid · Mefenamic acid · Tolfenamic acid Coxibs Celecoxib · Etoricoxib · Lumiracoxib · Parecoxib · Rofecoxib · Valdecoxib Other Nabumetone · Niflumic acid · Azapropazone · Glucosamine · Benzydamine · Glycosaminoglycan · Magnesium salicylate · Proquazone · Superoxide dismutase/Orgotein · Nimesulide · Feprazone · Diacerein · Morniflumate · Tenidap · Oxaceprol · Chondroitin sulfate

v • d • e Topical products for joint and muscular pain (M02) Anti-inflammatory preparations, non-steroids Butylpyrazolidines Phenylbutazone • Mofebutazone • Clofezone • Oxyphenbutazone Acetic acid derivatives Tolmetin • Diclofenac • Fentiazac Other Benzydamine • Etofenamate • Piroxicam • Felbinac • Bufexamac • Ketoprofen • Bendazac • Naproxen • Ibuprofen • Feprazone • Niflumic acid • Meclofenamic acid • Flurbiprofen • Suxibuzone • Indometacin • Nifenazone Capsaicin derivatives Zucapsaicin Other Tolazoline • Dimethyl sulfoxide

v • d • e Analgesic products (N02A, N02B) Opioids See also: Opioids template Opium & alkaloids thereof Codeine · Morphine · Opium · Laudanum · Paregoric Semi-synthetic opium derivatives Acetyldihydrocodeine · Benzylmorphine · Desomorphine · Dihydrocodeine · Dihydromorphine · Ethylmorphine · Diamorphine · Hydrocodone · Hydromorphinol · Hydromorphone · Nicocodeine · Nicodicodeine · Nicomorphine · Oxycodone · Oxymorphone · Dihydrocodeinone  · Buprenorphine · Synthetic opioids Alphaprodine · Anileridine · Butorphanol · Dextromoramide · Dextropropoxyphene · Dezocine · Fentanyl · Ketobemidone · Levorphanol · Methadone · Meptazinol · Nalbuphine · Pentazocine · Propoxyphene · Propiram · Pethidine · Phenazocine · Piminodine · Piritramide · Tapentadol · Tilidine · Tramadol · Pyrazolones Ampyrone/Aminophenazone · Metamizole · Phenazone · Propyphenazone Cannabinoids Ajulemic acid · AM404 · Cannabidiol · Cannabis · Nabilone · Tetrahydrocannabinol Anilides Paracetamol (acetaminophen) · Phenacetin · Propacetamol Non-steroidal anti-inflammatories See also: NSAIDs template Propionic acid class Fenoprofen · Flurbiprofen · Ibuprofen · Ketoprofen · Naproxen · Oxaprozin Oxicam class Meloxicam · Piroxicam Acetic acid class Diclofenac · Indometacin · Ketorolac · Nabumetone · Sulindac · Tolmetin COX-2 inhibitors Celecoxib · Rofecoxib · Valdecoxib · Parecoxib · Lumiracoxib Anthranilic acid (fenamate) class Meclofenamate · Mefenamic acid Salicylates Aspirin (Acetylsalicylic acid) · Benorylate · Diflunisal · Ethenzamide · Magnesium salicylate · Salicin · Salicylamide · Salsalate · Trisalate · Wintergreen (Methyl salicylate) Atypical, adjunct and potentiators, miscellaneous Befiradol · Bicifadine · Camphor · Clonidine · Cyclobenzaprine · Duloxetine · Flupirtine · Gabapentin · Glafenine · Menthol · Nefopam · Orphenadrine · Scopolamine · Tebanicline · Trazodone · Ziconotide

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