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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
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.Naproxen sodium (INN) (pronounced /nəˈprɒksən/) is a non-steroidal anti-inflammatory drug (NSAID) commonly used for the reduction of intense 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.^ Aleve is in a group of drugs called nonsteroidal anti-inflammatory drugs (NSAIDs).

• Aleve - Anti-Inflammatory Drugs 15 September 2009 4:12 UTC www.weight-loss-center.net [Source type: General]

^ Because most episodes of back pain have inflammation as a contributing factor, anti-inflammatory medication such as non-steroidal anti-inflammatory drugs (NSAIDs) is often an effective pain medication treatment option.

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^ Naproxen is a medicine that is commonly used to reduce pain, inflammation, and stiffness.

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.It works by inhibiting both the COX-1 and COX-2 enzymes.^ It works by inhibiting both the COX-1 and COX-2 enzymes.

• About: Naproxen 6 January 2010 10:54 UTC dbpedia.org [Source type: Academic]

^ Nonselective NSAIDs inhibit both COX-1 and COX-2, whereas COX-2-specific inhibitors have a minimal effect on COX-1.

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^ NSAID inhibit the enzyme cyclooxygenase (COX; also referred to as prostaglandin synthetase), blocking the production of prostaglandins (PG).

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.Naproxen and naproxen sodium are marketed under various trade names including: Aleve, Anaprox, Antalgin, Feminax Ultra, Flanax, Inza, Midol Extended Relief, Miranax, Naprelan, Naprogesic, Naprosyn, Narocin, Proxen, Synflex, Xenobid.^ ANAPROX naproxen sodium respectively.

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^ Where Found: Naproxen sodium is sold under a variety of different brand names, including: .

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^ I'm assuming you mean sodium naproxen, brand name Aleve?

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.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.^ Common Name naproxen In this drug factsheet: .

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^ Naproxen is a drug available without any prescription.

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^ ANAPROX naproxen sodium respectively.

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.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.^ Use the prescription and over-the-counter drugs.

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^ Drug more naproxen use .

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^ Naproxen was approved for the named allele!

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.In Australia, packets of 275 mg tablets of naproxen sodium are Schedule 2 Pharmacy Medicines, with a maximum daily dose of 5 tablets/1375 mg.^ In Australia, small packets of lower-strength preparations of naproxen sodium are Schedule 2 Pharmacy Medicines.

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^ Naproxen is taken regularly scheduled, dose.

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^ Naproxen and naproxen sodium are generic medicines.

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.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].^ Naproxen 250 mg-WAT .

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^ Naproxen was approved for the named allele!

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^ Naproxen 250 mg-DAV .

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.Aleve became available over-the-counter in most provinces in Canada on July 14, 2009 with the exception of Quebec, Newfoundland and Labrador.^ Tuesday, July 14, 2009 .

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^ Aleve became available over-the-counter in most provinces in Canada on July 14, 2009 with the exception of British Columbia and Newfoundland and Labrador.

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^ Any most provinces in Canada you may need dosage may cause vision problems.

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^[2] .Although later becoming available behind the counter in the province of Quebec (you need to ask the pharmacist to get it, though you don't need a prescription), Newfoundland and Labrador.^ Ask your pharmacist any questions you have about refilling your prescription.

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^ Ask your pharmacist if you do not have one.

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^ Q. Do I need to have a prescription from a doctor to purchase from you?

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Contents 1 Structure and details 2 Synthesis 3 Adverse effects and warnings 3.1 Drug Interactions 3.2 Naproxen link to Pseudoporphyria 3.3 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.^ Naproxen is a member of the 2-arylpropionic acid (profen) family of NSAIDs.

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^ Naproxen is also not recommended for use with NSAIDs of the salicylate family (drugs may reduce each other's effects), nor with anticoagulants (may increase risk of bleeding).

• Naproxen: Encyclopedia of chemistry, analytics & pharmaceutics with 64,557 entries. 6 January 2010 10:54 UTC www.chemie.de [Source type: Academic]

^ Naproxen is a member of the arylacetic acid group of nonsteroidal anti-inflammatory drugs.The chemical name for naproxen is (S)-6-methoxy--methyl-2-naphthaleneacetic acid.

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.The free acid is an odorless, white to off-white crystalline substance.^ It is an odorless, white to off-white crystalline substance.

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^ It is an odourless, white to off-white crystalline substance.

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^ It is lipid soluble, practically insoluble in water at low pH and freely soluble in water at high pH. Naproxen sodium is a white to creamy white, crystalline solid, freely soluble in water at neutral pH. .

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.It is lipid-soluble and practically insoluble in water.^ It is lipid -soluble and practically insoluble in water.

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^ It is lipid soluble, practically insoluble in water at low pH and freely soluble in water at high pH. Naproxen sodium is a white to creamy white, crystalline solid, freely soluble in water at neutral pH. .

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.It has a melting point of 153 °C.^ It has a melting point of 153 °C .

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Synthesis

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

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

Adverse effects and warnings

.Precautions should be used with the use of Naproxen (and other NSAIDs) in patients with a past medical history of asthma, blood clotting, GI ulcers, GI bleeding, GI perforation, liver disease, kidney disease, hypertension or heart failure because Naproxen may worsen these conditions.^ Naproxen should be used for.

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^ These medications may cause constipation.

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^ This medication may be on your medical condition.

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.Discretion should be used in late-term pregnant women, anemic, dehydrated or elderly patients.^ What other drugs used in elderly patients?

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^ Patients should not consume alcoholic beverages or use prescription or non-prescription medications containing alcohol while on naproxen tramadol therapy.

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^ Patients with initial hemoglobin values of 10 g or less who are to receive long-term therapy should have hemoglobin values determined frequently.

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^[4] .The most common system to be affected by adverse reactions to naproxen is the gastrointestinal tract.^ Naproxen may diminish the gastrointestinal tract.

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^ Adverse Reactions: The most common adverse reactions encountered with NSAIDs are gastrointestinal, of which peptic ulcer, with or without bleeding, is the most severe.

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^ Gastrointestinal System: There is no definitive evidence that the concomitant administration of histamine H 2 -receptor antagonists and/or antacids will either prevent the occurrence of gastrointestinal side effects or allow the continuation of naproxen therapy when and if these adverse reactions appear.

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.As mentioned above, these adverse events includes GI bleeding and GI ulceration, and incidence of these reactions show a direct relationship both to dose as well as to duration of use.^ The incidence of these complications increases with increasing dose.

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^ These serious adverse events are idiosyncratic and are independent of dose or duration of use.

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^ A low incidence of adverse events was found but these were poorly reported.

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^[5][6] .In addition, when taking Naproxen, an individual may also experience blurred vision, confusion and drowsiness.^ Alcohol Naproxen may cause drowsiness, dizziness, or blurred vision.

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^ Naproxen may cause drowsiness, dizziness, or blurred vision.

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^ Naproxen EC tablets may cause dizziness, drowsiness or affect your vision.

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.It is advised that patients on Naproxen use caution when driving or doing activities that require alertness.^ Use with caution, in patients.

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^ Nonprescription naproxen may require the use.

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^ CAUTION IS ADVISED WHEN USING Naproxen IN THE ELDERLY because they may be more sensitive to the effects of Naproxen, especially stomach bleeding and kidney effects.

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^[7]

.In August 2006, the Journal Birth Defects Research Part B 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.^ Heart attack and stroke: People who take NSAIDs have a higher risk of experiencing a heart attack or stroke.

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^ In August 2006, the journal Birth Defects Research Part B published results in the September issue 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.

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^ Other NSAIDs including naproxen in adults.

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^[8]

Drug Interactions

.When Naproxen is used in combination with methotrexate or aminoglycosides (for example, gentamicin) the blood levels of the methotrexate or aminoglycoside may increase, presumably because the elimination from the body is reduced.^ Naproxen may reduce the removal of the following medicines from the body and so may increase the blood levels and risk of side effects of these medicines.

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^ Warfarin's INRs may be increased by naproxen.

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^ Nonprescription naproxen may require the use.

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.This may lead to more methotrexate or aminoglycoside-related side effects.^ More results for 'naproxen side effects' .

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^ Dosage Side effects What it is used for more...

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^ CAUTION IS ADVISED WHEN USING Naproxen IN THE ELDERLY because they may be more sensitive to the effects of Naproxen, especially stomach bleeding and kidney effects.

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^[9]

.Like other NSAIDs, naproxen can inhibit the excretion of sodium and lithium.^ Other NSAIDs including naproxen in adults.

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^ Also like other NSAIDs, naproxen can inhibit the excretion of sodium and lithium.

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^ Its naproxen sodium,similar to the other anti inflammitories like ...

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.Extreme care must be taken by those who use this drug along with lithium supplements.^ The drugs should not be used by those who are allergic to aspirin .

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^ Lithium Lithium is a mineral that may be present in some supplements and is also used in large amounts to treat mood disorders such as manic-depression ( bipolar disorder ).

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^ Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use.

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.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).^ (NSAIDs) such as Aspirin, Ibuprofen and Naproxen .

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^ The concurrent use of aspirin and NSAIDs also increase the risk of serious gastrointestinal adverse effects.

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^ Take other drugs contain an NSAID (aspirin, ibuprofen, naproxen, or others).

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.Naproxen preparations containing sodium (e.g., Anaprox, Aleve, etc.^ Generic and brand names: naproxen sodium, oral; naproxen, oral; Aleve; Anaprox; Anaprox DS; EC-Naprosyn; Naprelan; Naprosyn; Pamprin Maximum Strength All Day Relief .

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^ Aleve, Aleve Caplet, Aleve Easy Open Arthritis, Aleve Gelcap, Anaprox, Anaprox-DS, Comfort Pac with Naproxen, EC-Naprosyn, Leader Naproxen Sodium, Midol Extended Relief, Naprelan '375', Naprelan '500', Naprosyn .

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^ V-R Naproxen Sodium contains salt (sodium).

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) 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.^ High blood pressure (hypertension) .

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^ Naproxen may reduce the blood pressure lowering effects of blood pressure medications.

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^ As explained above, this could be a key differentiating factor in the anti-inflammatory market, due to the growing recognition that current treatments can raise blood pressure.

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Naproxen link to Pseudoporphyria

.Naproxen has also been linked to cases of pseudoporphyria, specifically in those with skin type II or lower, especially with blue or green eyes.^ Click on one of the links below if you are concerned about a specific type of dog poisoning.

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^ In these cases, utilization of lower doses of naproxen should be considered and patients carefully monitored.

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Risk of heart attack or stroke

.The National Institutes of Health prematurely terminated a randomized clinical trial of naproxen and celecoxib for prevention of Alzheimer's disease, after preliminary data suggested similar effects to Vioxx, such as heart attack or stroke, in patients taking naproxen.^ This medicine does not prevent heart attack or stroke.

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^ National Institutes of health status.

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^ The National Institutes of Health (NIH) announced the suspension of an Alzheimer's disease prevention trial which used celecoxib, naproxen, or placebo.

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^[10]

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. ^ Naproxen. In: DrugPoints® System [Internet database]. Greenwood Village, Colo: Thomson Reuters (Healthcare) Inc. Updated periodically.
5. ^ RxList Internet Drug Index. "Naprosyn, Anaprox, Anaprox DS". http://www.rxlist.com/naprosyn-drug.htm
6. ^ WebMD. Naproxen Oral. http://www.webmd.com/drugs/mono-1289-NAPROXEN+-+ORAL.aspx?drugid=5173&drugname=Naproxen+Oral
7. ^ Marion, DW. Naproxen: Drug Information. In: UpToDate, Basow, DS (Ed). Waltham, MA, 2009.
8. ^ 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. 
9. ^ Jay Marks. MD. Medication and Drugs. http://www.medicinenet.com/naproxen/article.htm
10. ^ 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

.

• 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?^ Online NewsHour: Painkiller Naproxen May Increase Heart Attack and Stroke -- December 21, 2004 .
  • Online NewsHour: Painkiller Naproxen May Increase Heart Attack and Stroke -- December 21, 2004 6 January 2010 10:54 UTC www.pbs.org [Source type: FILTERED WITH BAYES]
  
  ^ Risk of heart attack of these naproxen findings.
  • NSAA : National Ski Areas Association : The GREENROOM 6 January 2010 10:54 UTC www.nsaa.org [Source type: Academic]
  
  ^ Naproxen is in a group of drugs called nonsteroidal anti-inflammatory drugs (NSAIDs).
  • Aleve (naproxen) medical facts from Drugs.com 15 September 2009 4:12 UTC www.drugs.com [Source type: FILTERED WITH BAYES]
  
  - Medscape
• U.S. National Library of Medicine: Drug Information Portal - Naproxen

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.

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 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

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

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, adjunct and potentiators, miscellaneous Befiradol · Bicifadine · Camphor · Clonidine · Cyclobenzaprine · Duloxetine · Esreboxetine · Flupirtine · Gabapentin · Glafenine · Hydroxyzine · Menthol · Nefopam · Orphenadrine · Pregabalin · Scopolamine · Tebanicline · Trazodone · Ziconotide

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

Categories: Non-steroidal anti-inflammatory drugs | Carboxylic acids | Equine medications | Naphthalenes | Phenol ethers

Hidden categories: Articles to be expanded from December 2009 | All articles to be expanded

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Alzheimer's Disease Anti-Inflammatory Prevention Trial - Alzheimer's Disease Anti-Inflammatory Prevention Trial (ADAPT) - Full Text View - ClinicalTrials.gov

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