naproxen

(nə-prŏk'sən)

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

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Brand names: Aflaxen™, Aleve®, Anaprox®, Anaprox® DS, Mediproxen®, Naprelan®, Naprelan® 375, Naprelan® 500, Naprosyn®, 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
• Naproxen Oral tablet, extended-release, Naproxen Oral tablet, extended-release
• Naproxen Sodium Oral capsule, liquid filled

Espa�ol:
• Naproxeno, Tableta oral de liberación retardada
• Naproxeno, Tableta oral
• Naproxeno Sódico, Tableta oral
• Naproxeno Sódico, Tableta oral de liberación prolongada
• Naproxeno, Suspensión oral
• Naproxeno, Tableta oral de liberación prolongada
• Naproxeno, Tableta oral de liberación prolongada
• Naproxeno Sódico, Cápsula oral llena de líquido

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 other medicines that contain aspirin, ibuprofen, or naproxen 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
Clinical data
Pregnancy cat.	C(AU) B(US)
Legal status	Pharmacy Only (S2) (AU) P (UK) OTC (US) OTC(Ca)
Routes	Oral
Pharmacokinetic data
Bioavailability	95% (oral)
Protein binding	99%
Metabolism	Hepatic (to 6-desmethylnaproxen)
Half-life	12–24 hours
Excretion	Renal
Identifiers
CAS number	22204-53-1 Y
ATC code	G02CC02 M01AE02, M02AA12
PubChem	CID 156391
DrugBank	APRD01135
ChemSpider	137720 Y
UNII	57Y76R9ATQ Y
KEGG	D00118 Y
ChEBI	CHEBI:7476 Y
ChEMBL	CHEMBL154 Y
Chemical data
Formula	C14H14O3
Mol. mass	230.259 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)/t9-/m0/s1 Y Key:CMWTZPSULFXXJA-VIFPVBQESA-N Y
N(what is this?)  (verify)

Naproxen sodium (INN) ( /nəˈprɒksən/) is a nonsteroidal anti-inflammatory drug (NSAID) commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as:

osteoarthritis kidney stones rheumatoid arthritis psoriatic arthritis

gout ankylosing spondylitis menstrual cramps tendinitis bursitis

It is also used for 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, Midol Extended Relief, Nalgesin, Naposin, Naprelan, Naprogesic, Naprosyn, Narocin, Proxen, Synflex and Xenobid.

Naproxen was originally marketed as the prescription drug Naprosyn by Syntex 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. In the United States, the Food and Drug Administration (FDA) approved its use as an over-the-counter (OTC) drug in 1994; OTC preparations in the U.S. are mainly marketed by Bayer HealthCare under the trade name Aleve and generic store brand formulations. In Australia, packets of 275 mg tablets of naproxen sodium are Schedule 2 pharmacy medicines, with a maximum daily dose of 5 tablets or 1375 mg. In the United Kingdom, 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 14 July 2009, it became available in Quebec during the summer of 2010 but can only be dispensed by a pharmacy employee after an assessment of the patient's needs. It most recently became available in British Columbia in March 2011. ^[2]

Contents 1 Risks and adverse effects 2 Structure and details 3 Synthesis 4 See also 5 References 6 External links

Risks and adverse effects

COX-2 selective and non-selective NSAIDs have been linked to increases in the number of serious and potentially fatal cardiovascular events such as myocardial infarctions and stroke. A 2011 meta-analysis published in the British Medical Journal states that, of all NSAIDs evaluated, naproxen was associated with the smallest overall cardiovascular risks.^[3] The drug had roughly 50% of the associated risk of stroke as compared with ibuprofen and was also associated with a reduced number of myocardial infarctions as compared to control groups.

As with other NSAIDs, naproxen can cause gastrointestinal problems such as heartburn, constipation, diarrhea, ulcers, and stomach bleeding ^[4], and those with a history of ulcers or inflammatory bowel disease should consult a doctor before taking naproxen. Consumption of alcohol may increase the risk of gastrointestinal complications.

NSAID Painkillers, such as Naproxen, may interfere and reduce efficiency of SSRI antidepressants ^[5][6]

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 152-154 °C.

Synthesis

Naproxen has been industrially produced by Syntex as follows:^[7]

Other synthetic routes have also been discussed.^[7]

See also

• Aspirin
• Paracetamol
• 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. ^ Trelle S, Reichenbach S, Wandel S, Hildebrand P, Tschannen B, Villiger PM, Egger M, Jüni P. (2011). "Cardiovascular safety of non-steroidal anti-inflammatory drugs: network meta-analysis". BMJ 342: c7086. doi:10.1136/bmj.c7086. PMC 3019238. PMID 21224324. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3019238. 
4. ^ Naproxen - PubMed Health
5. ^ Why Painkillers Interfere with Anti-depressants
6. ^ J.L. Warner-Schmidt et.al "Antidepressant effects of selective serotonin reuptake inhibitors (SSRIs) are attenuated by antiinflammatory drugs in mice and humans" PNAS 2011
7. ^ ^{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. 

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
• U.S. National Library of Medicine: Drug Information Portal - Naproxen

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 • Feprazone • Acetic acid derivatives and related substances Aceclofenac • Acemetacin • Alclofenac • Bromfenac • Bumadizone • Bufexamac • Diclofenac • Difenpiramide • Etodolac • Fentiazac • Indometacin • Ketorolac • Lonazolac • Oxametacin • Proglumetacin • Sulindac • Tolmetin • Zomepirac • Amfenac 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 • Niflumic acid • Morniflumate • Azapropazone • Coxibs Celecoxib • Etoricoxib • Lumiracoxib • Parecoxib • Rofecoxib • Valdecoxib Other Nabumetone • Glucosamine • Benzydamine • Glycosaminoglycan • Magnesium salicylate • Proquazone • Superoxide dismutase/Orgotein • Nimesulide • Diacerein • Tenidap • Oxaceprol • Chondroitin sulfate M: MUS, DF+DRCT anat (h/n, u, t/d, a/p, l)/phys/devp/hist noco(m, s, c)/cong(d)/tumr, sysi/epon, injr proc, drug (M1A/3)

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 • Idrocilamide

v d e Analgesics (N02A, N02B) Opioids See also: Opioids template Opium & alkaloids thereof Codeine# • Morphine# • Opium • Laudanum • Paregoric Semi-synthetic opium derivatives Acetyldihydrocodeine • Benzylmorphine • Buprenorphine • Desomorphine • Dihydrocodeine • Dihydromorphine • Ethylmorphine • Diamorphine • Hydrocodone • Hydromorphinol • Hydromorphone • Nicocodeine • Nicodicodeine • Nicomorphine • Oxycodone • Oxymorphone 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 • Nabiximols • 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, adjuvant and potentiators, Metabolic agents and miscellaneous Amitryptiline  • Befiradol • Bicifadine • Carisoprodol  • Camphor • Cimetidine • Clonidine • Chlorzoxazone • Cyclobenzaprine • Duloxetine • Esreboxetine • Flupirtine • Gabapentin • Glafenine • Hydroxyzine • Ketamine  • Menthol • Mephenoxalone • Methocarbamol • Nefopam • Orphenadrine • Pregabalin • Proglumide • Scopolamine • Tebanicline • Trazodone • Gabapentin enacarbil • Ziconotide #WHO-EM ‡Withdrawn from market Clinical trials: †Phase III §Never to phase III M: CNS anat(n/s/m/p/4/e/b/d/c/a/f/l/g)/phys/devp noco(m/d/e/h/v/s)/cong/tumr, sysi/epon, injr proc, drug(N1A/2AB/C/3/4/7A/B/C/D)

v d e Prolactin inhibitors and anti-inflammatory products for vaginal administration (G02CB–G02CC) Prolactin inhibitors Bromocriptine • Lisuride • Cabergoline • Quinagolide • Metergoline • Terguride Anti-inflammatory products for vaginal administration Ibuprofen • Naproxen • Benzydamine • Flunoxaprofen

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