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
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	12–15 hours
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	C(AU) B(US) Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... A section of the Anatomical Therapeutic Chemical Classification System. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... This article or section does not cite any references or sources. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... BIC pen cap, about 1 gram. ... The mole (symbol: mol) is the SI base unit that measures an amount of substance. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... A drugs efficacy may be affected by the degree to which it binds to the proteins within blood plasma. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The liver is an organ in vertebrates including humans. ... It has been suggested that Effective half-life be merged into this article or section. ... The hour (symbol: h) is a unit of time. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... Kidneys viewed from behind with spine removed The kidneys are bean-shaped excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... Anthem Advance Australia Fair Royal anthem: God Save the Queen Capital Canberra Largest city Sydney Official languages English (de facto 1) Government Federal constitutional monarchy and parliamentary democracy  -  Queen Elizabeth II  -  Governor-General Michael Jeffery  -  Prime Minister John Howard Independence from the United Kingdom   -  Constitution 1 January 1901   -  Statute of... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...
Legal status	Pharmacy Only (S2)(AU) POM(UK) OTC(US) ℞-only(Ca) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... The Standard for the Uniform Scheduling of Drugs and Poisons, abbreviated SUSDP, is a document used in the regulation of drugs and poisons in Australia. ... Anthem Advance Australia Fair Royal anthem: God Save the Queen Capital Canberra Largest city Sydney Official languages English (de facto 1) Government Federal constitutional monarchy and parliamentary democracy  -  Queen Elizabeth II  -  Governor-General Michael Jeffery  -  Prime Minister John Howard Independence from the United Kingdom   -  Constitution 1 January 1901   -  Statute of... A prescription drug is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained. ... Over-the-counter (OTC) drugs are medicines that may be sold without a prescription and without a visit to a medical professional, in contrast to prescription drugs. ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from... Motto (Latin for From Sea to Sea) Anthem O Canada Royal anthem: God Save the Queen Capital Ottawa Largest city Toronto Official languages English, French Government Parliamentary democracy and federal constitutional monarchy  -  Monarch Queen Elizabeth II  -  Governor General Michaëlle Jean  -  Prime Minister Stephen Harper Establishment  -  Act of Union February...
Routes	Oral

Naproxen (INN) (IPA: [nəˈprɒksən]) is a non-steroidal anti-inflammatory drug (NSAID) 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, injury (like fractures), menstrual cramps, tendonitis, bursitis, and the treatment of primary dysmenorrhea. Naproxen and naproxen sodium are marketed under various trade names including: Aleve, Anaprox, Naprogesic, Naprosyn, Naprelan, Synflex. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... Articles with similar titles include the NATO phonetic alphabet, which has also informally been called the “International Phonetic Alphabet”. For information on how to read IPA transcriptions of English words, see IPA chart for English. ... Non-steroidal anti-inflammatory drugs, usually abbreviated to NSAIDs, are drugs with analgesic, antipyretic and anti-inflammatory effects - they reduce pain, fever and inflammation. ... “Hurting” redirects here. ... An analogue medical thermometer showing the temperature of 38. ... An abscess on the skin, showing the redness and swelling characteristic of inflammation. ... Osteoarthritis / Osteoarthrosis (OA, also known as degenerative arthritis, degenerative joint disease, arthrosis or in more colloquial terms wear and tear), is a condition in which low-grade inflammation results in pain in the joints, caused by wearing of the cartilage that covers and acts as a cushion inside joints. ... Rheumatoid arthritis (RA) is traditionally considered a chronic, inflammatory autoimmune disorder that causes the immune system to attack the joints. ... Psoriatic arthritis (or Arthropathic psoriasis) is a type of inflammatory arthritis that affects around 20% of people suffering from the chronic skin condition Psoriasis. ... Menstrual cramps are spasmodic pains felt in the low abdomen, lower back and the upper thighs during the bleeding phase of a womans menstrual period. ... Tendonitis (also tenonitis or tendinitis) is an inflammation of a tendon. ... Bursitis is the inflammation of one or more bursae, or small sacs of synovial fluid, in the body. ... Dysmenorrhea (or dysmenorrhoea), cramps or painful menstruation, involves menstrual periods that are accompanied by either sharp, intermittent pain or dull, aching pain, usually in the pelvis or lower abdomen. ...

Naproxen was first and 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, small packets of lower-strength preparations of naproxen sodium are Schedule 2 Pharmacy Medicines. A prescription drug is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained. ... Year 1976 (MCMLXXVI) was a leap year starting on Thursday (link will display full calendar) of the 1976 Gregorian calendar. ... Year 1980 (MCMLXXX) was a leap year starting on Tuesday (link displays the 1980 Gregorian calendar). ... FDA logo The Food and Drug Administration (FDA) is an agency of the United States Department of Health and Human Services and is responsible for regulating food, dietary supplements, drugs, biological medical products, blood products, medical devices, radiation-emitting devices, veterinary products, and cosmetics in the United States. ... Over-the-counter substances, also abbreviated OTC, are drugs and other medical remedies that may be sold without a prescription and without a visit to a medical professional, in contrast to prescription only medicines (POM). ... Year 1994 (MCMXCIV) was a common year starting on Saturday (link will display full 1994 Gregorian calendar). ... The Standard for the Uniform Scheduling of Drugs and Poisons, abbreviated SUSDP, is a document used in the regulation of drugs and poisons in Australia. ...

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, practically insoluble in water with a low pH (below pH 4), while freely soluble in water at 6 pH and above. It has a melting point of 153 °C. A polyunsaturated triglyceride. ... The correct title of this article is . ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... Celsius is, or relates to, the Celsius temperature scale (previously known as the centigrade scale). ...

Adverse effects and warnings

Like other NSAIDs, naproxen is capable of producing disturbances in the gastrointestinal tract. Addition of a proton pump inhibitor such as esomeprazole will prevent this adverse effect. Naproxen in combination with a proton pump inhibitor is the safest NSAID combination. Upper and Lower gastrointestinal tract The gastrointestinal tract (GI tract), also called the digestive tract, or the alimentary canal, is the system of organs within multicellular animals that takes in food, digests it to extract energy and nutrients, and expels the remaining waste. ... Proton pump inhibitors (or PPIs) are a group of drugs whose main action is pronounced and long-lasting reduction of gastric acid production. ... Esomeprazole is a proton pump inhibitor used in the treatment of dyspepsia, peptic ulcer disease (PUD), GERD and Zollinger-Ellison syndrome. ... An adverse drug reaction (abbreviated ADR) is a term to describe the unwanted, negative consequences sometimes associated with the use of medications. ...

Also 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 (drugs may reduce each other's effects), nor with anticoagulants (may increase risk of bleeding). Certain preparations of naproxen are not recommended for use in patients with hypertension, as they contain sodium, worsening the effects of hypertension. General Name, Symbol, Number sodium, Na, 11 Chemical series alkali metals Group, Period, Block 1, 3, s Appearance silvery white Standard atomic weight 22. ... Lithium salts are chemical salts of lithium used as mood stabilizing drugs, primarily in the treatment of bipolar disorder, depression, and mania; but also in treating schizophrenia. ... Salicylic acid is a colorless, crystalline organic carboxylic acid. ... An anticoagulant is a substance that prevents coagulation; that is, it stops blood from clotting. ... This article or section does not cite any references or sources. ...

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.

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 an increased risk of major cardiovascular events, such as heart attack or stroke, in patients taking naproxen. However, recent meta-analyses which took into account all data from significant clinical trials of naproxen, including randomized clinical trials and observational trials concluded that naproxen carries no increased risk of heart attack or stroke at any commonly used dose. This stands in contrast to other NSAIDS, such as rofecoxib (Vioxx), celecoxib (Celebrex), and diclofenac, which did show significantly increased risk at some or all dosages. In February of 2007, the American Heart Association released a scientific statement advising that, when possible, physicians should avoid using NSAIDs in patients at high risk for heart disease. When pain relief is necessary, the AHA advises that doctors should preferentially use acetaminophen or certain older, non-COX-2 selective NSAIDs. The National Institutes of Health (NIH) is the primary agency of the United States government responsible for medical research. ... Celecoxib (INN) (IPA: ) is a non-steroidal anti-inflammatory drug (NSAID) used in the treatment of osteoarthritis, rheumatoid arthritis, acute pain, painful menstruation and menstrual symptoms, and to reduce numbers of colon and rectum polyps in patients with familial adenomatous polyposis. ... Acute myocardial infarction (AMI or MI), more commonly known as a heart attack, is a disease state that occurs when the blood supply to a part of the heart is interrupted. ... Stroke is the clinical designation for a rapidly developing loss of brain function due to an interruption in the blood supply to all or part of the brain. ... A meta-analysis is a statistical practice of combining the results of a number of studies. ... Rofecoxib (IPA: ) is a nonsteroidal anti-inflammatory drug (NSAID) developed by Merck & Co. ... Celecoxib (INN) (IPA: ) is a non-steroidal anti-inflammatory drug (NSAID) used in the treatment of osteoarthritis, rheumatoid arthritis, acute pain, painful menstruation and menstrual symptoms, and to reduce numbers of colon and rectum polyps in patients with familial adenomatous polyposis. ... Diclofenac (marketed as Voltaren®, Voltarol®, Diclon®, Dicloflex® Difen and Cataflam®) is a non-steroidal anti-inflammatory drug (NSAID) taken to reduce inflammation and an analgesic reducing pain in conditions such as in arthritis or acute injury. ... The American Heart Association (AHA) is a non-profit organization in the United States that fosters appropriate cardiac care in an effort to reduce disability and deaths caused by cardiovascular disease and stroke. ... Acetaminophen (USAN) or paracetamol (INN), is a popular analgesic and antipyretic drug that is used for the relief of fever, headaches, and other minor aches and pains. ...

External links

• CID 1302 from PubChem
• EINECS number 244-838-7
• MedlinePlus Information on naproxen
• FDA Statement on Naproxen, released December 20, 2004
• Alzheimer's Disease Anti-Inflammatory Prevention Trial