Naproxen  

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	1224 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 /nprksn/) 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]

Structure and details

Naproxen is a member of the 2-arylpropionic acid (profen) family of NSAIDs. It 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.

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^[3] 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^[4] 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

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

Recent Naproxen Forums  View All  

Is This Naproxen? 93/149 pink oblong pill with 93 on one side 149 on other side Tuesday, 11/10/2009 11:03:52 PM  2 Replies

Naproxen I took a 500mg Naproxen yesterday, it took it a second to kick in. I was having a real bad headache and a friend gave me one. When I got to work I started feeling really relaxed and dizzy. It was like my body felt like puddy or I had no bones in my body. Is it suppose to make me feel this way? True enough the headache was gone and I felt like a totally different person but I didn't like the side affects it caused. Friday, 11/6/2009 10:25:53 AM  4 Replies

Naproxen Taking naproxen long term. I now have ITP which I am told the purpura in thnis drug side effect is low blood platelets. Monday, 8/31/2009 8:38:52 AM  Post a Reply

Naproxen I have just been diagnosed with ITP; I am told it could be caused from the medication Naproxin because of purpura ingredient. We have been seeing several doctors and on 9/20/09 we have consultation for treatment. My platelets keep dropping and are around 60,000. I am sick almost all day, no energy, red spots, head ache I also have a condition in my legs that is called Lumpadema, swelling and has been being treated along with the arthritis. No one told us of this side effect and what could happen. Is this tempoary or now long term with treatment? Thursday, 8/20/2009 7:52:34 PM  3 Replies

What Is Naproxen WHAT IS IT USED FOR, PAIN PILL OR ANTI INFLAMATORY Thursday, 8/6/2009 2:46:37 PM  1 Reply

Naproxen Does naproxen make you tired? Monday, 7/6/2009 7:02:24 PM  2 Replies

Blue Pill G.... so i found a pill in my room, i have never seen it before, wanted to know what it's used for and what it actually is....Blue oval pill with a big G on left and and O or a 0 on the right? is it Naproxen? Monday, 6/22/2009 7:37:11 PM  Post a Reply

Naproxen Pill? I'm wondering if my pharmacy has given me the correct prescription. The pills are light orange, one side says 149, other side 93, oval in shape. The prescription is supposed to be for naproxen, 500mg Monday, 3/2/2009 3:51:05 PM  8 Replies

Mova 500 - Naproxen I found this pill in my kids room...just wondering do people use this as a drug for getting high..? Please let me know Thursday, 12/18/2008 7:29:59 AM  2 Replies

Naproxin Regular Use? My pediotrist put me on 375 mg. of naproxin....it has relieved my arthritic pain 90%...can one stay on this drug very long???? I would like to stay on it forever!! since they took vioxx off the mkt. I am in constant pain. Thanks Addie Wednesday, 8/20/2008 8:28:23 AM  2 Replies