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Ibuprofen is a medication in the nonsteroidal anti-inflammatory drug (NSAID) class that is used for treating pain, fever, and inflammation.
Common side effects include heartburn and a rash.
Ibuprofen was discovered in 1961 by Stewart Adams and initially marketed as Brufen.
Contents
1 Medical uses
1.1 Ibuprofen lysine
2 Adverse effects
2.1 Cardiovascular risk
2.2 Skin
2.3 Interactions
2.4 Overdose
2.5 Miscarriage
3 Pharmacology
4 Chemistry
4.1 Stereochemistry
5 History
6 Society and culture
6.1 Marketing
6.2 North America
7 Research
8 References
9 External links
Medical uses
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Ibuprofen is used primarily to treat fever (including post-vaccination fever), mild to moderate pain (including pain relief after surgery ), painful menstruation, osteoarthritis, dental pain, headaches, and pain from kidney stones. About 60% of people respond to any NSAID; those who do not respond well to a particular one may respond to another.
It is used for inflammatory diseases such as juvenile idiopathic arthritis and rheumatoid arthritis.
Ibuprofen lysine
In some countries, ibuprofen lysine (the lysine salt of ibuprofen, sometimes called “ibuprofen lysinate”) is licensed for treatment of the same conditions as ibuprofen; the lysine salt is used because it is more water-soluble.
Adverse effects
See also: Nonsteroidal anti-inflammatory drug
Adverse effects include nausea, dyspepsia, diarrhea, constipation, gastrointestinal ulceration/bleeding, headache, dizziness, rash, salt and fluid retention, and high blood pressure.
Infrequent adverse effects include esophageal ulceration, heart failure, high blood levels of potassium, kidney impairment, confusion, and bronchospasm.
Ibuprofen may be quantified in blood, plasma, or serum to demonstrate the presence of the drug in a person having experienced an anaphylactic reaction, confirm a diagnosis of poisoning in people who are hospitalized, or assist in a medicolegal death investigation. A monograph relating ibuprofen plasma concentration, time since ingestion, and risk of developing renal toxicity in people who have overdosed has been published.
Cardiovascular risk
Along with several other NSAIDs, chronic ibuprofen use has been found correlated with risk of hypertension
Skin
Along with other NSAIDs, ibuprofen has been associated with the onset of bullous pemphigoid or pemphigoid-like blistering.
Interactions
Drinking alcohol when taking ibuprofen may increase the risk of stomach bleeding.
According to the US Food and Drug Administration (FDA), “ibuprofen can interfere with the antiplatelet effect of low-dose aspirin, potentially rendering aspirin less effective when used for cardioprotection and stroke prevention.” Allowing sufficient time between doses of ibuprofen and immediate-release (IR) aspirin can avoid this problem. The recommended elapsed time between a dose of ibuprofen and a dose of aspirin depends on which is taken first. It would be 30 minutes or more for ibuprofen taken after IR aspirin, and eight hours or more for ibuprofen taken before IR aspirin. However, this timing cannot be recommended for enteric-coated aspirin. But, if ibuprofen is taken only occasionally without the recommended timing, the reduction of the cardioprotection and stroke prevention of a daily aspirin regimen is minimal.
Overdose
Ibuprofen overdose has become common since it was licensed for OTC use. Many overdose experiences are reported in the medical literature, although the frequency of life-threatening complications from ibuprofen overdose is low. The severity of symptoms varies with the ingested dose and the time elapsed; however, individual sensitivity also plays an important role. Generally, the symptoms observed with an overdose of ibuprofen are similar to the symptoms caused by overdoses of other NSAIDs.
Correlation between severity of symptoms and measured ibuprofen plasma levels is weak. Toxic effects are unlikely at doses below 100 mg/kg, but can be severe above 400 mg/kg (around 150 tablets of 200 mg units for an average man); A precise lethal dose is difficult to determine, as it may vary with age, weight, and concomitant conditions of the individual person.
Therapy is largely symptomatic. In cases presenting early, decontamination of the stomach is recommended. This is achieved using activated charcoal ; charcoal adsorbs the drug before it can enter the bloodstream. Gastric lavage is now rarely used, but can be considered if the amount ingested is potentially life-threatening, and it can be performed within 60 minutes of ingestion. Purposeful vomiting is not recommended.
Miscarriage
A study of pregnant women suggests that those taking any type or amount of NSAIDs (including ibuprofen, diclofenac and naproxen ) were 2.4 times more likely to miscarry than those not taking the medications.
Pharmacology
NSAIDs such as ibuprofen work by inhibiting the cyclooxygenase (COX) enzymes, which convert arachidonic acid to prostaglandin H 2 (PGH 2 ). PGH 2, in turn, is converted by other enzymes to several other prostaglandins (which are mediators of pain, inflammation, and fever) and to thromboxane A 2 (which stimulates platelet aggregation, leading to the formation of blood clots ).
Like aspirin and indomethacin, ibuprofen is a nonselective COX inhibitor, in that it inhibits two isoforms of cyclooxygenase, COX-1 and COX-2. The analgesic, antipyretic, and anti-inflammatory activity of NSAIDs appears to operate mainly through inhibition of COX-2, which decreases the synthesis of prostaglandins involved in mediating inflammation, pain, fever, and swelling. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation. Inhibition of COX-1 instead would be responsible for unwanted effects on the gastrointestinal tract.
Ibuprofen is administered as a racemic mixture. The R-enantiomer undergoes extensive interconversion to the S-enantiomer in vivo. The S-enantiomer is believed to be the more pharmacologically active enantiomer.
Chemistry
Ibuprofen is practically insoluble in water, but very soluble in most organic solvents like ethanol (66.18 g/100mL at 40 °C for 90% EtOH), methanol, acetone and dichloromethane.
The original synthesis of ibuprofen by the Boots Group started with the compound 2-methylpropylbenzene. The synthesis took six steps. A modern, greener technique for the synthesis involves only three steps.
Stereochemistry
( R )-ibuprofen
( S )-ibuprofen
It is an optically active compound with both S and R -isomers, of which the S (dextrorotatory) isomer is the more biologically active; this isomer has also been isolated and used medically (see dexibuprofen for details).
Ibuprofen is produced industrially as a racemate. The compound, like other 2-arylpropionate derivatives (including ketoprofen, flurbiprofen, naproxen, etc.), does contain a stereocenter in the α-position of the propionate moiety. So two enantiomers of ibuprofen occur, with the potential for different biological effects and metabolism for each enantiomer.
An isomerase ( alpha-methylacyl-CoA racemase ) converts ( R )-ibuprofen to the active ( S )- enantiomer.
History
Ibuprofen was derived from propionic acid by the research arm of Boots Group during the 1960s.
Society and culture
Marketing
See also: Ibuprofen brand names
A bottle of generic ibuprofen
Ibuprofen was made available under prescription in the United Kingdom in 1969, and in the United States in 1974. Ibuprofen is its INN, BAN, AAN and USAN approved name. Advil is manufactured by Pfizer and has been on the market since 1984.
North America
Ibuprofen is commonly available in the United States up to the FDA’s 1984 dose limit OTC, rarely used higher by prescription.
Research
This section needs to be updated. Please update this article to reflect recent events or newly available information. Last update: PMID   25227314, PMID   25644018 (November 2017)
Ibuprofen is sometimes used for the treatment of acne because of its anti-inflammatory properties, and has been sold in Japan in topical form for adult acne.
Ibuprofen has been associated with a lower risk of Parkinson’s disease, and may delay or prevent it. Aspirin, other NSAIDs, and paracetamol (acetaminophen) had no effect on the risk for Parkinson’s.
Some dietary supplements might be dangerous to take along with ibuprofen and other NSAIDs, but as of 2016

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