Ibuprofen
Systematic (IUPAC) name
2-[4-(2-methylpropyl)phenyl]propanoic acid
Identifiers
CAS number	15687-27-1
ATC code	M01AE01
PubChem	3672
DrugBank	APRD00372
Chemical data
Formula	C13H18O2
Mol. mass	206.3 g/mol
SMILES	eMolecules & PubChem
Physical data
Melt. point	76 °C (169 °F)
Pharmacokinetic data
Bioavailability	49–73%
Protein binding	99%
Metabolism	Hepatic
Half life	1.8–2 hours
Excretion	Renal
Therapeutic considerations
Licence data	US Image File history File links Download high resolution version (1100x516, 26 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Ibuprofen ... 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. ... 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. ... A chemical formula is an easy way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... This article is about the chemistry of hydrogen. ... This article is about the chemical element and its most stable form, or dioxygen. ... 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). ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... The melting point of a solid is the temperature range at which it changes state from solid to liquid. ... 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 biological half-life of a substance is the time required for half of that substance to be removed from an organism by either a physical or a chemical process. ... The kidneys are important excretory organs in vertebrates. ... The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ...
Pregnancy cat.	C(AU) D(US) 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. ... For other uses, see Australia (disambiguation). ... For other uses of terms redirecting here, see US (disambiguation), USA (disambiguation), and United States (disambiguation) Motto In God We Trust(since 1956) (From Many, One; Latin, traditional) Anthem The Star-Spangled Banner Capital Washington, D.C. Largest city New York City National language English (de facto)1 Demonym American...
Legal status	Unscheduled(AU) GSL(UK) OTC(US) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... For other uses, see Australia (disambiguation). ... Over-the-counter (OTC) drugs are medicines that may be sold without a prescription, in contrast to prescription drugs. ... For other uses of terms redirecting here, see US (disambiguation), USA (disambiguation), and United States (disambiguation) Motto In God We Trust(since 1956) (From Many, One; Latin, traditional) Anthem The Star-Spangled Banner Capital Washington, D.C. Largest city New York City National language English (de facto)1 Demonym American...
Routes	Oral, rectal and topical

Coated 200 mg ibuprofen tablets

Ibuprofen (INN) (IPA: /ˌaɪbjuːˈpɹəʊfɛn/) (from the earlier and no longer correct nomenclature iso-butyl-propanoic-phenolic acid) is a non-steroidal anti-inflammatory drug (NSAID) originally marketed as Brufen, and since then under various other trademarks (see tradenames section), most notably Advil and Motrin. It is used for relief of symptoms of arthritis, primary dysmenorrhea, fever, and as an analgesic, especially where there is an inflammatory component. Ibuprofen is known to have an antiplatelet effect, though it is relatively mild and short-lived when compared to that of aspirin or other more well-known antiplatelet drugs. Ibuprofen is a core medicine in the World Health Organization's "Essential Drugs List", which is a list of minimum medical needs for a basic health care system.^[1] 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. ... 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. ... Non-steroidal anti-inflammatory drugs, usually abbreviated to NSAIDs, are drugs with analgesic, antipyretic and anti-inflammatory effects - they reduce pain, fever and inflammation. ... “(TM)” redirects here. ... It has been suggested that this article or section be merged with ibuprofen. ... Arthritis (from Greek arthro-, joint + -itis, inflammation; plural: arthritides) is a group of conditions where there is damage caused to the joints of the body. ... Dysmenorrhea (or dysmenorrhoea) is a medical condition characterized by severe uterine pain during menstruation. ... An analogue medical thermometer showing the temperature of 38. ... An analgesic (colloquially known as a painkiller) is any member of the diverse group of drugs used to relieve pain (achieve analgesia). ... An abscess on the skin, showing the redness and swelling characteristic of inflammation. ... An antiplatelet drug is a member of a class of pharmaceuticals that decreases platelet aggregation and inhibits thrombus formation. ... This article is about the drug. ... WHO redirects here. ... The World Health Organization (WHO) Model List of Essential Medicines is a guideline for national governments that want to ensure they have an inventory of medicines needed by every health system. ...

History

Ibuprofen was developed by the research arm of Boots Group during the 1960s^[2]. It was discovered by Stewart Adams, with colleagues John Nicholson and Colin Burrows and was patented in 1961. The drug was launched as a treatment for rheumatoid arthritis in the United Kingdom in 1969, and in the United States in 1974. Famously, it is recorded that Dr. Adams initially tested his drug on a hangover. He was subsequently awarded an OBE in 1987. Boots was awarded the Queen's Award For Technical Achievement for the development of the drug in 1987.^[3] This article is about a former British company which has now merged to form Alliance Boots, as a result, information on this page may be out of date. ... The 1960s decade refers to the years from the beginning of 1960 to the end of 1969. ... For other uses, see Patent (disambiguation). ... Year 1961 (MCMLXI) was a common year starting on Sunday (link will display full calendar) of the Gregorian calendar. ... Rheumatoid arthritis (RA) is traditionally considered a chronic, inflammatory autoimmune disorder that causes the immune system to attack the joints. ... Also: 1969 (number) 1969 (movie) 1969 (Stargate SG-1) episode. ... Year 1974 (MCMLXXIV) was a common year starting on Tuesday (link will display full calendar) of the 1974 Gregorian calendar. ... For other uses, see Hangover (disambiguation). ... The Most Excellent Order of the British Empire is a British order of chivalry established on 4 June 1917 by King George V. The Order includes five classes in civil and military divisions; in decreasing order of seniority, these are Knight Grand Cross or Dame Grand Cross (GBE) Knight Commander... This article is about the year 1987. ...

Typical administration

Low doses of ibuprofen (200 mg, and sometimes 400 mg) are available over the counter (OTC) in most countries. Ibuprofen has a dose-dependent duration of action of approximately 4–8 hours, which is longer than suggested by its short half-life. The recommended dose varies with body mass and indication. Generally, the oral dose is 200–400 mg (5–10 mg/kg in children) every 4–6 hours, adding up to a usual daily dose of 800–1200 mg. 1200 mg is considered the maximum daily dose for over-the-counter use, though under medical direction, a maximum daily dose of 3200 mg may sometimes be used in increments of 600–800 mg. Over-the-counter (OTC) drugs are medicines that may be sold without a prescription, in contrast to prescription drugs. ... The biological half-life of a substance is the time required for half of that substance to be removed from an organism by either a physical or a chemical process. ... Medical Direction, or Online Medical Direction, allows a Paramedic to contact a physician from the field via radio or other means to obtain instructions on further care of a patient. ...

Ibuprofen is also available in topical form, which is absorbed through the skin, and can be used for sports injuries, with less risk of gastrointestinal problems.^{[citation needed]}

Off-label and investigational use

• As with other NSAIDs, ibuprofen may be useful in the treatment of severe orthostatic hypotension.^[4]
• In some studies, ibuprofen showed superior results compared to placebo in the prophylaxis of Alzheimer's disease, when given in low doses over a long time.^[5] Further studies are needed to confirm the results before ibuprofen can be recommended for this indication.
• Ibuprofen has been associated with a lower risk of Parkinson's disease, and may delay or prevent Parkinson's disease. Aspirin, other NSAIDs, and paracetamol had no effect on the risk for Parkinson's.^[6] Further research is warranted before recommending ibuprofen for this use.

Orthostatic hypotension (also known as postural hypotension, orthostatic intolerance and, colloquially, as head rush or a dizzy spell) is a sudden fall in blood pressure, typically greater than 20/10 mm Hg, that occurs when a person assumes a standing position, usually after a prolonged period of rest. ... Prophylaxis refers to any medical or public health procedure whose purpose is to prevent, rather than treat or cure, disease. ... Paracetamol (INN) (IPA: ) or acetaminophen (USAN) is a widely-used analgesic and antipyretic. ...

Ibuprofen lysine

In Europe, Australia, and New Zealand, ibuprofen lysine (ibuprofen lysinate, the lysine salt of ibuprofen) is licensed for treatment of the same conditions as ibuprofen. The lysine salt increases water solubility, allowing the medication to be administered intravenously.^[7] Ibuprofen lysine has been shown to have a more rapid onset of action compared to base ibuprofen.^[8] Lysine is one of the 20 amino acids normally found in proteins. ...

Ibuprofen lysine is indicated for closure of a patent ductus arteriosus in premature infants weighing between 500 and 1500 grams, who are no more than 32 weeks gestational age when usual medical management (e.g., fluid restriction, diuretics, respiratory support, etc.) is ineffective.^[7] With regard to this indication, ibuprofen lysine is an effective alternative to intravenous indomethacin and may be advantageous in terms of renal function.^[9] Patent ductus arteriosus (PDA) is a congenital heart defect wherein a childs ductus arteriosus fails to close after birth. ... Indomethacin (USAN) or indometacin (INN) is a non-steroidal anti-inflammatory drug commonly used to reduce fever, pain, stiffness, and swelling. ...

Mechanism of action

Ibuprofen is an NSAID which is believed to work through inhibition of cyclooxygenase (COX), thus inhibiting prostaglandin synthesis. There are at least 2 variants of cyclooxygenase (COX-1 and COX-2). Ibuprofen inhibits both COX-1 and COX-2. It appears that its analgesic, antipyretic, and anti-inflammatory activity are achieved principally through COX-2 inhibition; whereas COX-1 inhibition is responsible for its unwanted effects on platelet aggregation and the GI mucosa. The role of the individual COX isoforms in the analgesic, anti-inflammatory and gastric damage effects of NSAIDs is uncertain and different compounds cause different degrees of analgesia and gastric damage.^[10] Cyclooxygenase (COX) is an enzyme (EC 1. ... E1 - Alprostadil I2 - Prostacyclin A prostaglandin is any member of a group of lipid compounds that are derived enzymatically from fatty acids and have important functions in the animal body. ... An analgesic (colloquially known as a painkiller) is any member of the diverse group of drugs used to relieve pain (achieve analgesia). ... Antipyretics are drugs that prevent or reduce fever by lowering the body temperature from a raised state. ... Inflammation is the first response of the immune system to infection or irritation and may be referred to as the innate cascade. ... A 250 ml bag of newly collected platelets. ...

Adverse effects

Main article: Non-steroidal anti-inflammatory drug

Ibuprofen appears to have the lowest incidence of gastrointestinal adverse drug reactions (ADRs) of all the non-selective NSAIDs. However, this only holds true at lower doses of ibuprofen, so over-the-counter preparations of ibuprofen are generally labeled to advise a maximum daily dose of 1,200 mg. Non-steroidal anti-inflammatory drugs, usually abbreviated to NSAIDs, are drugs with analgesic, antipyretic and anti-inflammatory effects - they reduce pain, fever and inflammation. ... An adverse drug reaction (abbreviated ADR) or adverse drug event (abbreviated ADE) is an expression that describes the unwanted, negative consequences associated with the use of given medications. ...

Common adverse effects include: nausea, dyspepsia, gastrointestinal ulceration/bleeding, raised liver enzymes, diarrhea, epistaxis, headache, dizziness, unexplained rash, salt and fluid retention, and hypertension.^[11] For other uses, see Nausea (disambiguation). ... Liver function tests (LFTs or LFs), which include liver enzymes, are groups of clinical biochemistry laboratory blood assays designed to give information about the state of a patients liver. ... In medicine, diarrhea, also spelled diarrhoea (see spelling differences), refers to frequent loose or liquid bowel movements. ... For the plant referred to as nosebleed plant, see Yarrow. ... A headache (cephalgia in medical terminology) is a condition of pain in the head; sometimes neck or upper back pain may also be interpreted as a headache. ... Many different terms are often used to describe what is collectively known as dizziness. ... For other forms of hypertension, see Hypertension (disambiguation). ...

Infrequent adverse effects include: oesophageal ulceration, heart failure, hyperkalaemia, renal impairment, confusion, bronchospasm, and rash.^[11] Congestive heart failure (CHF), also called congestive cardiac failure (CCF) or just heart failure, is a condition that can result from any structural or functional cardiac disorder that impairs the ability of the heart to fill with or pump a sufficient amount of blood throughout the body. ... Hyperkalemia (hyper is high, kalium is the Latin name for potassium) is an elevated blood level (above 5. ... Renal failure or kidney failure is a situation in which the kidneys fail to function adequately. ... Bronchospasm is a difficulty in breathing caused by a sudden constriction of the muscles in the walls of the bronchioles. ...

Very infrequent adverse effects include Stevens-Johnson syndrome. Stevens-Johnson syndrome (SJS) is a severe and life-threatening condition. ...

Photosensitivity

As with other NSAIDs, ibuprofen has been reported to be a photosensitising agent.^[12][13] However, this only rarely occurs with ibuprofen and it is considered to be a very weak photosensitising agent when compared with other members of the 2-arylpropionic acid class. This is because the ibuprofen molecule contains only a single phenyl moiety and no bond conjugation, resulting in a very weak chromophore system and a very weak absorption spectrum which does not reach into the solar spectrum. Photosensitivity is the amount to which an object reacts upon receiving photons of light. ... In chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the functional group with the formula -C6H5 Picture where the six carbon atoms are arranged in a cyclic manner. ... Look up moiety in Wiktionary, the free dictionary. ... A chemically conjugated system, is a system of atoms covalently bonded with alternating single and double bonds (e. ... A chromophore is part (or moiety) of a molecule responsible for its color. ...

Cardiovascular risk

Along with several other NSAIDs, ibuprofen has been implicated in elevating the risk of myocardial infarction, particularly among those chronically using high doses.^[14] Heart attack redirects here. ...

Risks in pregnancy

Two studies have found an increased risk of miscarriage with the use of NSAIDs such as ibuprofen early in pregnancy^{[citation needed]}; however, several other studies did not find this association.^{[citation needed]} There are also concerns that drugs such as ibuprofen may interfere with implantation of the early fetus, although a clear risk has not been established. Miscarriage or spontaneous abortion is the natural or spontaneous end of a pregnancy at a stage where the embryo or the fetus is incapable of surviving, generally defined in humans at a gestation of prior to 20 weeks. ... Implantation is a phenomenon in prenatal development, i. ...

When ibuprofen is used as directed in the first and second trimester of pregnancy, it is not associated with an increased risk for birth defects. However, ibuprofen is generally not the pain reliever of choice during pregnancy because there are concerns with the use of ibuprofen during the third trimester. The human gestation period of approximately 40 weeks between the time of the last menstrual cycle and delivery is traditionally divided into three periods of three months, or trimesters. ... A congenital disorder is a medical condition or defect that is present at or before birth (for example, congenital heart disease). ...

Risks in Inflammatory Bowel Disease (IBD)

Ibuprofen is never to be used in individuals with Inflammatory Bowel Disease (IBD-Crohn's Disease and Ulcerative Colitis) due to its ability to cause gastric bleeding and form ulceration in the gastric lining. Drugs such as Advil should be avoided in persons afflicted with IBD. Pain relievers such as Tylenol (containing acetaminophen) or drugs containing Codeine (which slows down bowel activity) are safer methods than Ibuprofen for pain relief in IBD. Ibuprofen is also known to cause worsening of IBD during times of a flare-up, thus should be avoided completely. In medicine, inflammatory bowel disease (IBD) is a group of inflammatory conditions of the large intestine and, in some cases, the small intestine. ... Crohns disease (also known as regional enteritis) is a chronic, episodic, inflammatory bowel disease (IBD) and is generally classified as an autoimmune disease. ... Ulcerative colitis (Colitis ulcerosa, UC) is a form of inflammatory bowel disease (IBD). ...

Stereochemistry

Ibuprofen, like other 2-arylpropionate derivatives (including ketoprofen, flurbiprofen, naproxen, etc), contains a chiral carbon in the α-position of the propionate moiety. As such, there are two possible enantiomers of ibuprofen, with the potential for different biological effects and metabolism for each enantiomer. Ketoprofen, (RS)2-(3-benzoylphenyl)-propionic acid (chemical formula C16H14O3) is one of the propionic acid class of non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic effects. ... Flurbiprofen is an NSAID (non-steroidal anti-inflammatory drug) used to treat the inflammation and pain of arthritis. ... Naproxen (INN) (IPA: ) 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... The propionate (also propanoate) ion is C2H5COO− (propionic acid minus one hydrogen ion). ... In chemistry, enantiomers (from the Greek ἐνάντιος, opposite, and μέρος, part or portion) are stereoisomers that are nonsuperimposable complete mirror images of each other, much as ones left and right hands are the same but opposite. ...

Indeed it was found that (S)-(+)-ibuprofen (dexibuprofen) was the active form both in vitro and in vivo. Dexibuprofen is a non-steroidal anti-inflammatory drug. ...

It was logical, then, that there was the potential for improving the selectivity and potency of ibuprofen formulations by marketing ibuprofen as a single-enantiomer product (as occurs with naproxen, another NSAID).

Further in vivo testing, however, revealed the existence of an isomerase (2-arylpropionyl-CoA epimerase) which converted (R)-ibuprofen to the active (S)-enantiomer.^[15][16][17] Thus, due to the expense and futility that might be involved in making a pure enantiomer, most ibuprofen formulations currently marketed are racemic mixtures. In biochemistry, an isomerase is an enzyme that catalyses the interconversion of polymers. ... In chemistry, enantiomers (from the Greek ἐνάντιος, opposite, and μέρος, part or portion) are stereoisomers that are nonsuperimposable complete mirror images of each other, much as ones left and right hands are the same but opposite. ... In chemistry, a racemate is a mixture of equal amounts of left- and right-handed stereoisomers of a chiral molecule. ...

(R)-ibuprofen	(S)-ibuprofen

Human toxicology

Ibuprofen overdose has become common since it was licensed for over-the-counter use. There are many overdose experiences reported in the medical literature, although the frequency of life-threatening complications from ibuprofen overdose is low.^[18] Human response in cases of overdose ranges from absence of symptoms to fatal outcome in spite of intensive care treatment. Most symptoms are an excess of the pharmacological action of ibuprofen and include abdominal pain, nausea, vomiting, drowsiness, dizziness, headache, tinnitus, and nystagmus. Rarely more severe symptoms such as gastrointestinal bleeding, seizures, metabolic acidosis, hyperkalaemia, hypotension, bradycardia, tachycardia, atrial fibrillation, coma, hepatic dysfunction, acute renal failure, cyanosis, respiratory depression, and cardiac arrest have been reported.^[19] 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. A medical journal is a scientific journal devoted to the field of medicine. ... Abdominal pain can be one of the symptoms associated with transient disorders or serious disease. ... Heaving redirects here. ... Tinnitus (pronounced or ,[1] from the Latin word for ringing[2]) is the perception of sound in the human ear in the absence of corresponding external sound(s). ... Nystagmus is involuntary eye movement that can be part of the vestibulo-ocular reflex (VOR), with the eyes moving first in the direction of the lesioned side (slow phase) followed by a quick correction (fast phase) to the opposite side or away from the lesioned side. ... Gastrointestinal bleeding describes every form of hemorrhage (blood loss) in the gastrointestinal tract, from the pharynx to the rectum. ... This article is about the medical condition. ... In medicine, metabolic acidosis is a state in which the blood pH is low (under 7. ... Hyperkalemia (hyper is high, kalium is the Latin name for potassium) is an elevated blood level (above 5. ... In physiology and medicine, hypotension refers to an abnormally low blood pressure. ... Bradycardia, as applied to adult medicine, is defined as a resting heart rate of under 60 beats per minute, though it is seldom symptomatic until the rate drops below 50 beat/min. ... This article or section does not cite any references or sources. ... Atrial fibrillation (AF or afib) is a cardiac arrhythmia (abnormal heart rhythm) that involves the two upper chambers (atria) of the heart. ... For other uses, see Coma (disambiguation). ... Cyanosis refers to the bluish coloration of the skin due to the presence of deoxygenated hemoglobin in blood vessels near the skin surface. ... In medicine, hypoventilation (also known as respiratory depression) occurs when ventilation is inadequate (hypo means below) to perform needed gas exchange. ... Wikipedia does not yet have an article with this exact name. ...

There is little correlation between severity of symptoms and measured ibuprofen plasma levels. Toxic effects are unlikely at doses below 100 mg/kg but can be severe above 400 mg/kg;^[20] however, large doses do not indicate that the clinical course is likely to be lethal.^[21] It is not possible to determine a precise lethal dose, as this may vary with age, weight, and concomitant diseases of the individual patient. A lethal dose (LD) is an indication of the lethality of a given substance or type of radiation. ...

Therapy is largely symptomatic. In cases presenting early, gastric decontamination is recommended. This is achieved using activated charcoal; charcoal absorbs the drug before it can enter the systemic circulation. 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. Emesis is not recommended.^[22] The majority of ibuprofen ingestions produce only mild effects and the management of overdose is straightforward. Standard measures to maintain normal urine output should be instituted and renal function monitored.^[20] Since ibuprofen has acidic properties and is also excreted in the urine, forced alkaline diuresis is theoretically beneficial. However, due to the fact ibuprofen is highly protein bound in the blood, there is minimal renal excretion of unchanged drug. Forced alkaline diuresis is therefore of limited benefit.^[23] Symptomatic therapy for hypotension, GI bleeding, acidosis, and renal toxicity may be indicated. Occasionally, close monitoring in an intensive care unit for several days is necessary. If a patient survives the acute intoxication, he/she will usually experience no late sequelae. Activated carbon (also called activated charcoal) is the more general term which includes material mostly derived from charcoal. ... Systemic circulation is the portion of the cardiovascular system which carries oxygenated blood away from the heart, to the body, and returns deoxygenated blood back to the heart. ... Gastric lavage, also commonly called a stomach pump, is the process of cleaning out the contents of the stomach. ... Heaving redirects here. ... In medicine (nephrology) renal function is an indication of the state of the kidney and its role in physiology. ... Forced diuresis (increased urine formation by diuretics and fluid) may enhance the excretion of certain drugs in urine and is used to treat drug overdose or poisoning of these drugs and hemorrhagic cystitis. ... ICU room An Intensive Care Unit (ICU) or Critical Care Unit (CCU) is a specialised department in a hospital that provides intensive care medicine. ... A sequela (plural sequelae) is a pathological condition resulting from a disease. ...

Availability

Ibuprofen was made available under prescription in the United Kingdom in 1969, and in the United States in 1974. In the years since, the good tolerability profile along with extensive experience in the community (otherwise known as Phase IV trials), has resulted in the rescheduling of small packs of ibuprofen to allow availability over-the-counter in pharmacies worldwide, as well as in supermarkets and other general retailers. Also: 1969 (number) 1969 (movie) 1969 (Stargate SG-1) episode. ... Year 1974 (MCMLXXIV) was a common year starting on Tuesday (link will display full calendar) of the 1974 Gregorian calendar. ... This box:      In health care, a clinical trial is a comparison test of a medication or other medical treatment (such as a medical device), versus a placebo (inactive look-a-like), other medications or devices, or the standard medical treatment for a patients condition. ... Over-the-counter (OTC) drugs are medicines that may be sold without a prescription, in contrast to prescription drugs. ... Supermarket produce section A supermarket is a store that sells a wide variety of goods including food and alcohol, medicine, clothes, and other household products that are consumed regularly. ...

For some time, there has been a limit on the amount that can be bought over the counter in a single transaction in the UK; this being 2 packs of 16 x 200 mg or 1 pack of 8 or 16 x 400 mg, the latter being far less common for over-the-counter sales. In the United States, the Food and Drug Administration approved it for over-the-counter use in 1984. The wider availability has meant that ibuprofen is now almost as commonly used as aspirin and paracetamol (acetaminophen).^{[citation needed]} In other countries, such as Spain, higher dosages of 600 mg are available. In Germany 600mg and 800mg per pill packages have to be prescribed, whereas 400mg is over-the-counter available in pharmacies. Mexico's doses go up to 800 mg per pill. Over-the-counter (OTC) drugs are medicines that may be sold without a prescription, in contrast to prescription drugs. ... FDA redirects here. ... This article is about the year. ... This article is about the drug. ... Paracetamol (INN) (IPA: ) or acetaminophen (USAN) is a widely-used analgesic and antipyretic. ...

Tradenames

Advil Liqui-Gels

• Act-3,
• Advil,
• Algofren (Greece),
• Alivium (Brazil),
• Arthrofen (UK),
• Bonifen by Krka d.d. (Slovenia),
• Brufen (Serbia, India, Pakistan, Portugal, South Korea, UK and New Zealand),
• Brufen Retard (UK),
• Burana (Finland),
• Calprofen (UK),
• Dalsy (Brazil),
• Dolgit (Germany , Czech Republic and Turkey)
• Doloraz (Jordan),
• Dolormin (Germany),
• Dorival,
• Ebufac (UK),
• Espidifen (Spain),
• Eve (Japan),
• Fenbid (UK),
• Fenpaed (Ireland and UK),
• Galprofen (UK),
• Hedex (Kenya and Uganda),
• Herron Blue (Australia),
• i-profen (New Zealand),
• Ibalgin (Czech Republic and Slovakia),
• Íbúfen (Iceland),
• Ibugel (UK),
• IbuHEXAL (Germany),
• Ibuleve (UK),
• Ibumax (Finland),
• Ibumetin (Denmark, Sweden and Latvia),
• Ibuprofen (Austria, Germany and Latvia),
• Ibuprom (Poland),
• IBU-Ratiopharm (Germany),
• Ibusal (Finland),
• Ibu-Vivimed (Austria and Germany)
• Ibux (Norway),
• Ibuxin (Finland),
• Ipren (Denmark and Sweden),
• Moment (Italy),
• Neofen (Croatia),
• Norvectan (Spain),
• Nuprin,
• Nurofen (Germany, France, Bulgaria, Ireland, Israel, Turkey, Australia, Russia, South Africa, Romania, UK and New Zealand, Cyprus),
• Orbifen (UK),
• Panafen,
• Perifar (Uruguay),
• Rimafen (UK),
• Speedpain NANO (South Korea)
• Spidifen (Belgium)

In the UK it is most commonly called Ibuprofen although can be called other trade names when used as an ingredient in decongestants and flu remedies. It has been suggested that this article or section be merged with ibuprofen. ... The United Kingdom of Great Britain and Northern Ireland is a country in western Europe, and member of the Commonwealth of Nations, the G8, the European Union, and NATO. Usually known simply as the United Kingdom, the UK, or (inaccurately) as Great Britain or Britain, the UK has four constituent... Krka d. ... Anthem:  Serbia() on the European continent()  —  [] Capital (and largest city) Belgrade Official languages Serbian Recognised regional languages Hungarian, Slovak, Romanian, Croatian, Rusyn 1 Albanian 2 Demonym Serbian Government Parliamentary Democracy  -  President Boris Tadić  -  Prime Minister Vojislav KoÅ¡tunica    -  First state 7th century   -  Serbian Kingdom3 1217   -  Serbian Empire 1345   -  Independence lost... The United Kingdom of Great Britain and Northern Ireland is a country in western Europe, and member of the Commonwealth of Nations, the G8, the European Union, and NATO. Usually known simply as the United Kingdom, the UK, or (inaccurately) as Great Britain or Britain, the UK has four constituent... The United Kingdom of Great Britain and Northern Ireland is a country in western Europe, and member of the Commonwealth of Nations, the G8, the European Union, and NATO. Usually known simply as the United Kingdom, the UK, or (inaccurately) as Great Britain or Britain, the UK has four constituent... The United Kingdom of Great Britain and Northern Ireland is a country in western Europe, and member of the Commonwealth of Nations, the G8, the European Union, and NATO. Usually known simply as the United Kingdom, the UK, or (inaccurately) as Great Britain or Britain, the UK has four constituent... The United Kingdom of Great Britain and Northern Ireland is a country in western Europe, and member of the Commonwealth of Nations, the G8, the European Union, and NATO. Usually known simply as the United Kingdom, the UK, or (inaccurately) as Great Britain or Britain, the UK has four constituent... The United Kingdom of Great Britain and Northern Ireland is a country in western Europe, and member of the Commonwealth of Nations, the G8, the European Union, and NATO. Usually known simply as the United Kingdom, the UK, or (inaccurately) as Great Britain or Britain, the UK has four constituent... The United Kingdom of Great Britain and Northern Ireland is a country in western Europe, and member of the Commonwealth of Nations, the G8, the European Union, and NATO. Usually known simply as the United Kingdom, the UK, or (inaccurately) as Great Britain or Britain, the UK has four constituent... The United Kingdom of Great Britain and Northern Ireland is a country in western Europe, and member of the Commonwealth of Nations, the G8, the European Union, and NATO. Usually known simply as the United Kingdom, the UK, or (inaccurately) as Great Britain or Britain, the UK has four constituent... The United Kingdom of Great Britain and Northern Ireland is a country in western Europe, and member of the Commonwealth of Nations, the G8, the European Union, and NATO. Usually known simply as the United Kingdom, the UK, or (inaccurately) as Great Britain or Britain, the UK has four constituent... The United Kingdom of Great Britain and Northern Ireland is a country in western Europe, and member of the Commonwealth of Nations, the G8, the European Union, and NATO. Usually known simply as the United Kingdom, the UK, or (inaccurately) as Great Britain or Britain, the UK has four constituent... The United Kingdom of Great Britain and Northern Ireland is a country in western Europe, and member of the Commonwealth of Nations, the G8, the European Union, and NATO. Usually known simply as the United Kingdom, the UK, or (inaccurately) as Great Britain or Britain, the UK has four constituent... The United Kingdom of Great Britain and Northern Ireland is a country in western Europe, and member of the Commonwealth of Nations, the G8, the European Union, and NATO. Usually known simply as the United Kingdom, the UK, or (inaccurately) as Great Britain or Britain, the UK has four constituent... The United Kingdom of Great Britain and Northern Ireland is a country in western Europe, and member of the Commonwealth of Nations, the G8, the European Union, and NATO. Usually known simply as the United Kingdom, the UK, or (inaccurately) as Great Britain or Britain, the UK has four constituent...

See also

• Aspirin
• Paracetamol (acetaminophen)

This article is about the drug. ... Paracetamol (INN) (IPA: ) or acetaminophen (USAN) is a widely-used analgesic and antipyretic. ...

References

Year 2006 (MMVI) was a common year starting on Sunday of the Gregorian calendar. ... is the 71st day of the year (72nd in leap years) in the Gregorian calendar. ... 2008 (MMVIII) is the current year, a leap year that started on Tuesday of the Common Era (or Anno Domini), in accordance with the Gregorian calendar. ... is the 20th day of the year in the Gregorian calendar. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... The Australian Medicines Handbook or AMH is a medical reference text commonly used in practice by health professionals (particularly general practitioners and pharmacists) in Australia. ... The United States National Library of Medicine (NLM), operated by the United States federal government, is the worlds largest medical library. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ...

External links

• U.S. National Library of Medicine: MedlinePlus Drug Information: Ibuprofen
• University of Bristol chemistry department page on Ibuprofen
• Ball and stick model
• Nurofen UK Website
• Over The Counter Drug Info