Molecular structure of Naproxen
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Anaprox

Naproxen (trade names: Aleve, Anaprox, Naprogesic, Naprosyn, Naprelan) 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, menstrual cramps, tendinitis, bursitis, and the treatment of primary dysmenorrhea. It works by reducing hormones that cause inflammation and pain in the body. more...

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Although naproxen typically requires a higher dosage than other NSAIDs — a minimal dose is about 200 mg — it binds very well to albumin and thus achieves a longer half-life in the blood than other drugs, lasting up to 12 hours per dose.

Naproxen is also available as a sodium salt, naproxen sodium, which is more rapidly absorbed from the gastrointestinal tract.

Naproxen was first sold as the prescription drug Naprosyn in 1976; naproxen sodium was first sold under the trade name Anaprox in 1980. The Food and Drug Administration (FDA) approved naproxen sodium's use as an over-the-counter drug in 1991 , and it is sold in the United States as Aleve. Naproxen is still a prescription drug in much of the world, including Canada.

Structure and details

Naproxen is a member of the arylacetic acid family of NSAIDs. It is an odorless, white to off-white crystalline substance with a molecular weight of 230.2628. 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. Naproxen has a melting point of 153 °C.

Side effects and warnings

Like other NSAIDs, naproxen is capable of producing disturbances in the gastrointestinal tract. Taking the medication with food may help to alleviate this most commonly reported side-effect.

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).

In December 2004, the FDA issued a press release following the decision by the National Institutes of Health to halt a five-year study, called the Alzheimer's Disease Anti-Inflammatory Prevention Trial. That study aimed to test both Aleve and Celebrex as preventatives for Alzheimer's disease. Preliminary information from the study showed naproxen elevated the risk of heart attack and stroke by 50%. The FDA advised patients taking over-the-counter naproxen products to:

  • carefully follow the instructions on the label,
  • avoid exceeding the recommended doses for naproxen (220 milligrams twice daily), and
  • take naproxen for no longer than ten days unless a physician directs otherwise.

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Nonsteroidal anti-inflammatory drugs
From Gale Encyclopedia of Medicine, 4/6/01 by Nancy Ross-Flanigan

Definition

Nonsteroidal anti-inflammatory drugs are medicines that relieve pain, swelling, stiffness, and inflammation.

Purpose

Nonsteroidal anti-inflammatory drugs (NSAIDs) are prescribed for a variety of painful conditions, including arthritis, bursitis, tendinitis, gout, menstrual cramps, sprains, strains, and other injuries.

Description

Nonsteroidal anti-inflammatory drugs relieve pain, stiffness, swelling, and inflammation, but they do not cure the diseases or injuries responsible for these problems. Two drugs in this category, ibuprofen and naproxen, also reduce fever. Some nonsteroidal anti-inflammatory drugs can be bought over the counter; others are available only with a prescription from a physician or dentist.

Among the drugs in this group are diclofenac (Voltaren), etodolac (Lodine), flurbiprofen (Ansaid), ibuprofen (Motrin, Advil, Rufen), ketorolac (Toradol), nabumetone (Relafen), naproxen (Naprosyn); naproxen sodium (Aleve, Anaprox, Naprelan); and oxaprozin (Daypro). They are sold as tablets, capsules, caplets, liquids, and rectal suppositories and some are available in chewable, extended-release, or delayed-release forms.

Recommended dosage

Recommended doses vary, depending on the patient, the type of nonsteroidal anti-inflammatory drug prescribed, the condition for which the drug is prescribed, and the form in which it is used. Always take nonsteroidal anti-inflammatory drugs exactly as directed. If using non-prescription (over-the-counter) types, follow the directions on the package label. For prescription types, check with the physician who prescribed the medicine or the pharmacist who filled the prescription. Never take larger or more frequent doses, and do not take the drug for longer than directed. Patients who take nonsteroidal anti-inflammatory drugs for severe arthritis must take them regularly over a long time. Several weeks may be needed to feel the results, so it is important to keep taking the medicine, even if it does not seem to be working at first.

When taking nonsteroidal anti-inflammatory drugs in tablet, capsule, or caplet form, always take them with a full, 8-ounce glass of water or milk. Taking these drugs with food or an antacid will help prevent stomach irritation.

Precautions

Nonsteroidal anti-inflammatory drugs can cause a number of side effects, some of which may be very serious (See Side effects). These side effects are more likely when the drugs are taken in large doses or for a long time or when two or more nonsteroidal anti-inflammatory drugs are taken together. Health care professionals can help patients weigh the risks of benefits of taking these medicines for long periods.

Do not take acetaminophen, aspirin, or other salicylates along with other nonsteroidal anti-inflammatory drugs for more than a few days unless directed to do so by a physician. Do not take ketorolac (Toradol) while taking other nonsteroidal anti-inflammatory drugs unless directed to do so by a physician.

Because older people are more sensitive than younger adults to nonsteroidal anti-inflammatory drugs, they may be more likely to have side effects. Some side effects, such as stomach problems, may also be more serious in older people.

Serious side effects are especially likely with one nonsteroidal anti-inflammatory drug, phenylbutazone. Patients age 40 and over are especially at risk of side effects from this drug, and the likelihood of serious side effects increases with age. Because of these potential problems, it is especially important to check with a physician before taking this medicine. Never take it for anything other than the condition for which it was prescribed, and never share it -- or any other prescription drug -- with another person.

Some nonsteroidal anti-inflammatory drugs can increase the chance of bleeding after surgery (including dental surgery), so anyone who is taking the drugs should alert the physician or dentist before surgery. Avoiding the medicine or switching to another type in the days prior to surgery may be necessary.

Some people feel drowsy, dizzy, confused, lightheaded, or less alert when using these drugs. Blurred vision or other vision problems also are possible side effects. For these reasons, anyone who takes these drugs should not drive, use machines or do anything else that might be dangerous until they have found out how the drugs affect them.

Nonsteroidal anti-inflammatory drugs make some people more sensitive to sunlight. Even brief exposure to sunlight can cause severe sunburn, rashes, redness, itching, blisters, or discoloration. Vision changes also may occur. To reduce the chance of these problems, avoid direct sunlight, especially from mid-morning to mid-afternoon; wear protective clothing, a hat, and sunglasses; and use a sunscreen with a skin protection factor (SPF) rating of at least 15. Do not use sunlamps, tanning booths or tanning beds while taking these drugs.

Special conditions

People with certain medical conditions and people who are taking some other medicines can have problems if they take nonsteroidal anti-inflammatory drugs. Before taking these drugs, be sure to let the physician know about any of these conditions:

Allergies

Let the physician know about any allergies to foods, dyes, preservatives, or other substances. Anyone who has had reactions to nonsteroidal anti-inflammatory drugs in the past should also check with a physician before taking them again.

Pregnancy

Women who are pregnant or who plan to become pregnant should check with their physicians before taking these medicines. Whether nonsteroidal anti-inflammatory drugs cause birth defects in people is unknown, but some do cause birth defects in laboratory animals. If taken late in pregnancy, these drugs may prolong pregnancy, lengthen labor time, cause problems during delivery, or affect the heart or blood flow of the fetus.

Breastfeeding

Some nonsteroidal anti-inflammatory drugs pass into breast milk. Women who are breastfeeding should check with their physicians before taking these drugs.

Other medical conditions

A number of medical conditions may influence the effects of nonsteroidal anti-inflammatory drugs. Anyone who has any of the conditions listed below should tell his or her physician about the condition before taking nonsteroidal anti-inflammatory drugs.

People who have sores or white spots in the mouth should tell the physician about them before starting to take nonsteroidal anti-inflammatory drugs. Sores or white spots that appear while taking the drug can be a sign of serious side effects.

  • Stomach or intestinal problems, such as colitis or Crohn's disease
  • Liver disease
  • Current or past kidney disease; current or past kidney stones
  • Heart disease
  • High blood pressure
  • Blood disorders, such as anemia, low platelet count, low white blood cell count
  • Bleeding problems
  • Diabetes mellitus
  • Hemorrhoids, rectal bleeding, or rectal irritation
  • Asthma
  • Parkinson's disease
  • Epilepsy
  • Systemic lupus erythematosus
  • Diseases of the blood vessels, such as polymyalgia rheumatica and temporal arteritis
  • Fluid retention
  • Alcohol abuse
  • Mental illness.
Special diets

Some nonsteroidal anti-inflammatory drugs contain sugar or sodium, so anyone on a low-sugar or low-sodium diet should be sure to tell his or her physician.

Smoking

People who smoke cigarettes may be more likely to have unwanted side effects from this medicine.

Use of certain medicines

Taking nonsteroidal anti-inflammatory drugs with certain other drugs may affect the way the drugs work or increase the risk of unwanted side effects. (See Interactions.)

Side effects

The most common side effects are stomach pain or cramps, nausea, vomiting, indigestion, diarrhea, heartburn, headache, dizziness or lightheadedness, and drowsiness. As the patient's body adjusts to the medicine, these symptoms usually disappear. If they do not, check with the physician who prescribed the medicine.

Serious side effects are rare, but do sometimes occur. If any of the following side effects occur, stop taking the medicine and get emergency medical care immediately:

  • Swelling or puffiness of the face
  • Swelling of the hands, feet, or lower legs
  • Rapid weight gain
  • Fainting
  • Breathing problems
  • Fast or irregular heartbeat
  • Tightness in the chest.

Other side effects do not require emergency medical care, but should have medical attention. If any of the following side effects occur, stop taking the medicine and call the physician who prescribed the medicine as soon as possible:

  • Severe pain, cramps, or burning in the stomach or abdomen
  • Convulsions
  • Fever
  • Severe nausea, heartburn, or indigestion
  • White spots or sores in the mouth or on the lips
  • Rashes or red spots on the skin
  • Any unusual bleeding, including nosebleeds, spitting up or vomiting blood or dark material
  • Black, tarry stool
  • Chest pain
  • Unusual bruising
  • Severe headaches.

A number of less common, temporary side effects are also possible. They usually do not need medical attention and will disappear once the body adjusts to the medicine. If they continue or interfere with normal activity, check with the physician. Among these side effects are:

  • Gas, bloating, or constipation
  • Bitter taste or other taste changes
  • Sweating
  • Restlessness, irritability, anxiety
  • Trembling or twitching.

Interactions

Nonsteroidal anti-inflammatory drugs may interact with a variety of other medicines. When this happens, the effects of the drugs may change, and the risk of side effects may be greater. Anyone who takes these drugs should let the physician know all other medicines he or she is taking. Among the drugs that may interact with nonsteroidal anti-inflammatory drugs are:

  • Blood thinning drugs, such as warfarin (Coumadin)
  • Other nonsteroidal anti-inflammatory drugs
  • Heparin
  • Tetracyclines
  • Cyclosprorine
  • Digitalis drugs
  • Lithium
  • Phenytoin (Dilantin)
  • Zidovudine (AZT, Retrovir).

Key Terms

Anemia
A lack of hemoglobin -- the compound in blood that carries oxygen from the lungs throughout the body and brings waste carbon dioxide from the cells to the lungs, where it is released.
Bursitis
Inflammation of the tissue around a joint
Colitis
Inflammation of the colon (large bowel)
Inflammation
Pain, redness, swelling, and heat that usually develop in response to injury or illness.
Salicylates
A group of drugs that includes aspirin and related compounds. Salicylates are used to relieve pain, reduce inflammation, and lower fever.
Tendinitis
Inflammation of a tendon -- a tough band of tissue that connects muscle to bone.

Further Reading

Gale Encyclopedia of Medicine. Gale Research, 1999.

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