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Naproxen
From Wikipedia, the free encyclopedia

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

1224 hours

Excretion

Renal

Identifiers

CAS number

22204-53-1

ATC code

G02CC02 M01AE02, M02AA12

PubChem

CID 156391

DrugBank

APRD01135

ChemSpider

137720

UNII

57Y76R9ATQ

KEGG

D00118

ChEBI

[1]

ChEMBL

CHEMBL154

Chemical data

Formula

C14H14O3

Mol. mass

230.259 g/mol

SMILES

eMolecules & PubChem

InChI[show]

(what is this?) (verify)

Naproxen sodium (INN) (

/nprksn/) is a nonsteroidal anti-inflammatory drug (NSAID)

commonly used for the reduction of pain, fever, inflammationand 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 COX1 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 Xenobi d. Naproxen was originally marketed as the prescription drug Naprosyn by Syntex in 1976, and naproxen sodium was first marketed under the trade nameAnaprox in 1980. It remains a prescriptiononly 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, with the exception of Quebec. It most recently became available in British Columbia in March 2011. [2]
Contents
[hide]

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

[edit]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 asmyocardial infarctions and stroke. A 2011 metaanalysis 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.

[edit]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.

[edit]Synthesis
Naproxen has been industrially produced by Syntex as follows:[4]

Other synthetic routes have also been discussed.[4]

[edit]See

also
Aspirin Paracetamol Ibuprofen

[edit]References

1. 2. 3.

^ Pocock, Nicola (2006). "MHRA approves availability of OTC naproxen (Feminax

Ultra)". NHS Press Release. ^ http://www.bayer.ca/files/Aleve%20Release.July14.FINAL_.pdf ^ Trelle S, Reichenbach S, Wandel S, Hildebrand P, Tschannen B, Villiger PM, Egger M,

Jni P. (2011). "Cardiovascular safety of non-steroidal anti-inflammatory drugs: network metaanalysis". BMJ 342: c7086. doi:10.1136/bmj.c7086. PMC 3019238. PMID 21224324.

4.

^ a b Peter J. Harrington and Eric Lodewijk (1997). "Twenty Years of Naproxen

Technology". Org. Process Res. Dev. 1 (1): 7276. doi:10.1021/op960009e.

[edit]External
Look

links

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

[show]v d eNon-steroidal anti-inflammatory drug (NSAID) products (prim

[show]v d eAnti-inflammatory products (M

[show]v d eTopical products for joint and muscula

[show]v d eAnalgesics (N02A, N02B)

[show]v d eProlactin inhibitors and anti-inflammatory products for vagin

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