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ibuprofen

 
(ī'byū-prō'fən) pronunciation
n.
A nonsteroidal anti-inflammatory medication, C13H18O2, used especially in the treatment of arthritis and commonly taken for its analgesic and antipyretic properties.

[Alteration of chemical name i(so)bu(tyl)phen(yl) pro(pionic acid).]


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Analgesic, one of the NSAIDs, especially effective against minor pain, fever, and inflammation. It works by inhibiting prostaglandin synthesis. It may irritate the gastrointestinal tract and should not be taken by anyone who has an allergy to aspirin or takes anticoagulants. Brand names include Advil, Motrin, and Nuprin. See also acetaminophen.

For more information on ibuprofen, visit Britannica.com.

Drug Info:

Diphenhydramine; Ibuprofen

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Diphenhydramine; Ibuprofen oral caplets

What are Diphenhydramine; Ibuprofen oral caplets?

DIPHENHYDRAMINE; IBUPROFEN (Advil® PM caplets) is a combination of two medicines used to help with sleeplessness due to minor aches and pains. Diphenhydramine is an antihistamine that causes drowsiness and ibuprofen reduces inflammation and helps relieve minor aches and pains.

What should I tell my health care provider before I take this medicine?

They need to know if you have any of these conditions:
• asthma, especially aspirin sensitive asthma, or chronic obstructive pulmonary disease (COPD)
• bleeding problems or taking medicines that make you bleed easily such as anticoagulants ('blood thinners')
• cigarette smoker
• coronary artery bypass graft (CABG) surgery within the past 2 weeks
• diabetes
• drink more than 3 alcohol-containing beverages a day
• glaucoma
• heart or circulation problems like angina, high blood pressure, heart failure, heart rhythm problems, history of heart attack, history of blood clots, or leg edema (fluid retention)
• kidney disease
• liver disease
• pain or difficulty passing urine
• prostate trouble
• stomach ulcers or pain
• history of stroke
• systemic lupus erythematosus
• thyroid disease
• ulcers or other stomach problems
• an unusual reaction to diphenhydramine, ibuprofen, aspirin, other medicines, foods, dyes, or preservatives
• pregnant or trying to get pregnant
• breast-feeding

How should this medicine be used?

Follow the directions on the label. Do not give more than directed or for a longer time. If diphenhydramine; ibuprofen causes stomach upset, it may be given with food or milk.

Contact your pediatrician or health care professional regarding the use of this medicine in children. Special care may be needed.

What if I miss a dose?

This does not apply. This medicine is only taken at bedtime when needed.

What drug(s) may interact with Diphenhydramine; Ibuprofen?

adefovir
• alcohol
amantadine
• anti-inflammatory drugs (other NSAIDs, prednisone)
• aspirin and aspirin-like medicines
bacitracin
cidofovir
cyclosporine
doxercalciferol
entecavir
foscarnet
ganciclovir
• herbal products that contain feverfew, garlic, ginger, or ginkgo biloba
• levofloxacin or ofloxacin
lithium
• medicines that affect platelets
• medicines for anxiety or sleeping problems, such as diazepam or temazepam
• medicines that treat or prevent blood clots such as warfarin and other 'blood thinners'
• medicines for cancer treatment or nausea/vomiting due to cancer
• medicines for for gastrointestinal problems
• medicines for hay fever and other allergies
• medicines for high blood pressure or irregular heart rate
• medicines for memory problems such as Alzheimer's disease
• medicines for mental depression
• medicines for mental problems and psychotic disturbances
• medicines for motion sickness
• medicines for movement abnormalities as in Parkinson's disease
• medicines for osteoporosis prevention and treatment
• medicines for rheumatoid arthritis
• medicines for seizure prevention
methotrexate
• muscle relaxants
• pain medicines
pemetrexed
pentamidine
• photosensitizing medicines
procarbazine
• stimulants
sulfinpyrazone
tacrolimus
• tenofovir
tretinoin, ATRA
voriconazole
• zoledronic acid

Tell your prescriber or health care professional about all other medicines you are taking, including non-prescription medicines, nutritional supplements, or herbal products. Also tell your prescriber or health care professional if you are a frequent user of drinks with caffeine or alcohol, if you smoke, or if you use illegal drugs. These may affect the way your medicine works. Check with your health care professional before stopping or starting any of your medicines.

What should I watch for while taking Diphenhydramine; Ibuprofen?

Do not take this product for longer than 10 days without consulting your health care provider. Seek medical attention if your pain does not improve or becomes more severe, or if sleeplessness continues for more than 2 weeks.

This product causes drowsiness. Do not drive, use machinery, or do anything that needs mental alertness after taking it. Do not sit or stand up quickly, especially if you are an older patient. This reduces the risk of dizzy or fainting spells.

Do not smoke cigarettes or drink alcohol; these increase irritation to your stomach and can make it more susceptible to damage from ibuprofen.

If you are going to have surgery, tell your prescriber or health care professional that you are taking a product containing ibuprofen. Problems can arise if you need dental work, and in the day to day care of your teeth. Try to avoid damage to your teeth and gums when you brush or floss your teeth.

It is especially important not to use this product during the last 3 months of pregnancy unless specifically directed to do so by your health care provider. Ibuprofen may cause problems in the unborn child or complications during delivery.

Your mouth may get dry. Chewing sugarless gum or sucking hard candy, and drinking plenty of water will help.

This medicine may cause dry eyes and blurred vision. If you wear contact lenses you may feel some discomfort. Lubricating drops may help. See an eye doctor if the problem does not go away or is severe.

Your skin may become more sensitive to the sun. Avoid prolonged sun exposure and use sunscreen while taking this medicine.

What side effects may I notice from receiving Diphenhydramine; Ibuprofen?

Side effects that you should report to your prescriber or health care professional as soon as possible:
• agitation, nervousness, excitability, not able to sleep (these are more likely in children)
• signs of bleeding - pinpoint red spots on the skin, black tarry stools, blood in the urine, unusual tiredness or weakness, vomiting blood or vomit that looks like coffee grounds
• blurred vision
• confusion
• difficulty breathing, wheezing, skin rash, redness, blistering or peeling skin, hives, or itching, swelling of eyelids, throat, lips
• dizziness or fainting spells
• hearing loss
• irregular heartbeat, palpitations, increased blood pressure, or chest pain
• nausea, vomiting, or severe heartburn
• pain or difficulty passing urine
• seizures (convulsions)
• stomach pain or cramps
• swelling of feet or ankles
• yellowing of eyes or skin

Side effects that usually do not require medical attention (report to your prescriber or health care professional if they continue or are bothersome):
• bruising
• change in appetite
• constipation or diarrhea
• dry mouth
• headache
• ringing in ears

Where can I keep my medicine?

Keep out of the reach of children in a container that small children cannot open.

Store at room temperature between 20 and 25 degrees C (68 and 77 degrees F). Keep container tightly closed. Throw away any unused medicine after the expiration date.

Last updated: 1/23/2006 11:12:00 AM

Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.


An non-steroidal anti-inflammatory drug used for the treatment of pain and inflammation in rheumatoid arthritis (including arthritis in children) and other disorders of the muscles or joints. It is also used to treat period pains, pain after surgery, and fever and pain in children. Ibuprofen is applied to the skin to relieve the pain of sprains, strains, bruises, and rheumatic and muscular pain. Ibuprofen has the lowest incidence of gastrointestinal side effects of all the non-steroidal anti-inflammatory drugs, but its anti-inflammatory effects are weaker. It is available as tablets, effervescent granules, modified-release tablets and capsules, a syrup, a gel for topical application, and a solution for injection. Some preparations are prescription only medicines. Some non-prescription preparations are freely available over the counter, but higher dosages and large pack sizes must be bought from pharmacies.

Side effects, precautions, and interactions with other drugs:
see non-steroidal anti-inflammatory drugs.

Proprietary preparations:
Anadin Ibuprofen; Anadin Ultra; Arthrofen; Boots Fever and Pain Relief 6 Months Plus Ibuprofen; Boots Ibuprofen Pain Relief 6 Months Plus; Brufen; Brufen Retard (modified-release tablets); Calprofen; Cuprofen; Cuprofen Gel; Cuprofen Maximum Strength; Ebufac; Fenbid Forte Gel; Fenbid Spansule (modified-release capsules); Hedex Ibuprofen; Ibrufhalal; Ibuderm; Ibufem; Ibugel (gel); Ibuleve (gel and spray); Ibumousse (foam); Ibuspray; Motrin; Nurofen; Nurofen for Children (suspension); Pedea (solution for injection); Proflex (tablets and cream); Radian B Ibuprofen Gel; Relcofen; Rimafen; Deep Relief (combined with menthol); Lemsip Flu 12 Hr (combined with pseudoephedrine); Non-Drowsy Sudafed Dual Relief Max (combined with pseudoephedrine); Nurofen Plus (combined with codeine); Solpadeine Migraine Ibuprofen & Codeine (combined with codeine).

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An analgesic drug derived from propionic acid. Ibuprofen is commonly used in sport as a non-steroidal anti-inflammatory drug (NSAID) to reduce swelling and pain, and accelerate recovery from soft tissue injuries.

Columbia Encyclopedia:

ibuprofen

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ibuprofen (ī'byūprō'fən), nonsteroidal anti-inflammatory drug (NSAID) that reduces pain, fever, and inflammation. Along with naproxen and ketoprofen, ibuprofen belongs to the propionic acid class of NSAIDs. It was first made available in 1967. Like other NSAIDs, it acts by inhibiting the body's production of prostaglandins. Available over the counter in a variety of preparations (e.g., Advil, Motrin, Nuprin), it is commonly used to treat rheumatoid arthritis, gout, and painful menstruation. Side effects include rash, alteration of platelet function and bleeding, and intestinal upset, which can lead to gastritis. Like other NSAIDS, it appears to have no potential for abuse or physical dependence. It should not be used by those who are allergic to aspirin.



2-(4-isobutylphenyl)propionic acid; a nonsteroidal anti-inflammatory agent of the substituted propionic acid type; others of this type are flurbiprofen, ketoprofen, and naproxen. They inhibit the cyclooxygenase activity of prostaglandin-endoperoxide synthase, reversibly over short time intervals, followed by time-dependent irreversible inactivation, due probably to conformational rather than covalent changes. The racemic mixture is present in many over-the-counter drugs, but the (S)-enantiomer is the active form. Proprietary names include: Advil; Brufen; Motrin.





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A nonsteroidal anti-inflammatory agent that possesses analgesic and antipyretic activities; used for symptomatic relief of rheumatoid arthritis and osteoarthritis in humans, but its use in dogs is limited by the occurrence of undesirable side-effects such as gastrointestinal hemorrhage.


n

trade names: Advil, Excedrin-IB, Midol-IB, Motrin IB; drug class: nonsteroidal antiinflammatory; action: inhibits prostaglandin synthesis by interfering with cycloox-genase needed for biosynthesis; possesses analgesic, antiinflammatory, antipyretic properties; uses: rheumatoid arthritis, osteoarthritis, mild-to-moderate pain. Ibuprofen is useful for the temporary relief of minor aches and pains associated with the common cold, toothache, muscular aches, minor arthritic pain, and menstrual cramps, and for the reduction of fever.

Random House Word Menu:

categories related to 'ibuprofen'

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Random House Word Menu by Stephen Glazier
For a list of words related to ibuprofen, see:
  • PHARMACOLOGY - ibuprofen: nonaspirin analgesic agent, esp. used to treat inflammation


Ibuprofen
Systematic (IUPAC) name
(RS)-2-(4-(2-methylpropyl)phenyl)propanoic acid
Clinical data
Trade names Advil, Brufen, Motrin, etc.
AHFS/Drugs.com monograph
MedlinePlus a682159
Licence data US FDA:link
Pregnancy cat. C(AU) D(US)
Legal status Unscheduled (AU) GSL (UK) OTC (US)
Routes Oral, rectal, topical, and intravenous
Pharmacokinetic data
Bioavailability 49–73%
Protein binding 99%
Metabolism Hepatic (CYP2C9)
Half-life 1.8–2 h
Excretion Renal
Identifiers
CAS number 15687-27-1 YesY
ATC code C01EB16 G02CC01 M01AE01 M02AA13
PubChem CID 3672
DrugBank DB01050
ChemSpider 3544 YesY
UNII WK2XYI10QM YesY
KEGG D00126 YesY
ChEBI CHEBI:5855 YesY
ChEMBL CHEMBL521 YesY
Chemical data
Formula C13H18O2 
Mol. mass 206.29 g/mol
SMILES eMolecules & PubChem
Physical data
Melt. point 76 °C (169 °F)
 YesY(what is this?)  (verify)
Coated 200 mg ibuprofen tablets

Ibuprofen (INN) (play /ˈbjuːprfɛn/ or /bjuːˈprfən/ eye-bew-proh-fən; from the nomenclature iso-butyl-propanoic-phenolic acid) is a nonsteroidal anti-inflammatory drug (NSAID) used for relief of symptoms of arthritis, constipation, fever,[1] as an analgesic (pain reliever), especially where there is an inflammatory component, and dysmenorrhea.

Ibuprofen is known to have an antiplatelet effect, though it is relatively mild and somewhat short-lived when compared with aspirin or other better-known antiplatelet drugs. In general, ibuprofen also acts as a vasodilator, having been shown to dilate coronary arteries and some other blood vessels. Ibuprofen is a core medicine in the World Health Organization's "WHO Model List of Essential Medicines", which is a list of minimum medical needs for a basic healthcare system.[2][3][4][5]

Ibuprofen was derived from propionic acid by the research arm of Boots Group during the 1960s.[6] It was discovered by Andrew RM Dunlop, with colleagues Stewart Adams, John Nicholson, Vonleigh Simmons, Jeff Wilson and Colin Burrows, and was patented in 1961. Originally marketed as Brufen, ibuprofen is available under a variety of popular trademarks, including Motrin, Nurofen, Advil, and Nuprin.[7]

Contents

Medical uses

Ibuprofen is used primarily for fever, pain, dysmenorrhea and inflammatory diseases such as rheumatoid arthritis.[8] It is also used for pericarditis and patent ductus arteriosus.[8]

Dosage

Ibuprofen has a dose-dependent duration of action of approximately four to eight hours, which is longer than suggested by its short half-life. The recommended dose varies with body mass and indication. 1,200 mg is considered the maximum daily dose for OTC (Over The Counter) use,[9] though, under medical direction, the maximum amount of ibuprofen for adults is 800 milligrams per dose or 3200 mg per day.[10]

Unlike aspirin, which breaks down in solution, ibuprofen is stable, and, thus, ibuprofen can be available in topical gel form, which is absorbed through the skin, and can be used for sports injuries, with less risk of digestive problems.[11]

Ibuprofen lysine

In Europe, Australia, and New Zealand, ibuprofen lysine (the lysine salt of ibuprofen, sometimes called "ibuprofen lysinate" even though the lysine is in cationic form) is licensed for treatment of the same conditions as ibuprofen. The lysine salt increases water solubility, allowing the medication to be administered intravenously. Ibuprofen lysine is indicated for closure of a patent ductus arteriosus in premature infants weighing between 500 and 1,500 grams (1 and 3 lb), who are no more than 32 weeks gestational age when usual medical management (e.g., fluid restriction, diuretics, respiratory support, etc.) is ineffective.[12]

With regard to this indication, ibuprofen lysine is an effective alternative to intravenous indomethacin, and may be advantageous in terms of kidney function.[13] Ibuprofen lysine has been shown to have a more rapid onset of action compared to acid ibuprofen.[14]

Adverse effects

Common adverse effects include: nausea, dyspepsia, gastrointestinal ulceration/bleeding, raised liver enzymes, diarrhea, constipation, epistaxis, headache, dizziness, priapism, rash, salt and fluid retention, and hypertension.[15][citation needed] A study from 2010 has shown regular use of NSAIDs was associated with an increase in hearing loss.[16]

Infrequent adverse effects include: esophageal ulceration, heart failure, hyperkalemia, renal impairment, confusion, and bronchospasm.[15]

Ibuprofen appears to have the lowest incidence of digestive adverse drug reactions (ADRs) of all the nonselective NSAIDs. However, this holds true only at lower doses of ibuprofen, so OTC preparations of ibuprofen are, in general, labeled to advise a maximum daily dose of 1,200 mg.[9]

Photosensitivity

As with other NSAIDs, ibuprofen has been reported to be a photosensitising agent.[17]

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.[citation needed]

Cardiovascular risk

Along with several other NSAIDs, ibuprofen has been implicated in elevating the risk of myocardial infarction (heart attack), in particular, among those chronically using high doses.[18]

Skin

Along with other NSAIDs, ibuprofen has been associated with the onset of bullous pemphigoid or pemphigoid-like blistering.[19]

Interactions

Drinking alcohol when taking ibuprofen increases risk of stomach bleeding.[10]

According to the U.S. Food and Drug Administration, "ibuprofen can interfere with the antiplatelet effect of low-dose aspirin (81 mg per day), potentially rendering aspirin less effective when used for cardioprotection and stroke prevention." Allowing sufficient time between doses of ibuprofen and immediate release aspirin can avoid this problem. The recommended elapsed time between a 400 mg 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 immediate release aspirin, and 8 hours or more for ibuprofen taken before immediate release 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.[20]

Erectile dysfunction risk

A 2005 study linked long term (over 3 months) use of NSAIDs, including ibuprofen, with a 1.4 times increased risk of erectile dysfunction.[21][22] The report by Kaiser Permanente and published in the Journal of Urology, considered that "regular non-steroidal anti-inflammatory drug use is associated with erectile dysfunction beyond what would be expected due to age and other condition".[23] The director of research for Kaiser Permanente added that "There are many proven benefits of non steroidals in preventing heart disease and for other conditions. People shouldn't stop taking them based on this observational study. However, if a man is taking this class of drugs and has ED, it's worth a discussion with his doctor".[22]

Overdose

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.[24] 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.[25] 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.

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 (around 150 tablets of 200 mg units for an average man);[26] however, large doses do not indicate the clinical course is likely to be lethal.[27] It is not possible to determine a precise lethal dose, as this may vary with age, weight, and concomitant diseases of the individual patient.

Therapy is largely symptomatic. In cases presenting early, gastric decontamination is recommended. This is achieved using activated charcoal; charcoal adsorbs 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.[28] 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.[26] Since ibuprofen has acidic properties and is also excreted in the urine, forced alkaline diuresis is theoretically beneficial. However, because ibuprofen is highly protein-bound in the blood, there is minimal renal excretion of unchanged drug. Forced alkaline diuresis is, therefore, of limited benefit.[29] Symptomatic therapy for hypotension, GI bleeding, acidosis, and renal toxicity may be indicated. On occasion, close monitoring in an intensive care unit for several days is necessary. If a patient survives the acute intoxication, he or she will usually experience no late sequelae.

Detection in body fluids

Ibuprofen may be quantitated 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 hospitalized patients, or assist in a medicolegal death investigation. A nomogram that relates the ibuprofen plasma concentration, time since ingestion, and risk of developing renal toxicity in overdose patients has been published.[30]

Miscarriage

A Canadian study published in the Canadian Medical Association Journal of thousands of pregnant woman suggests that those taking any type or amount of non-steroidal anti-inflammatory drugs (including ibuprofen, diclofenac and naproxen) were 2.4 times more likely to miscarry than those not taking the drugs.[31]

Mechanism of action

Nonsteroidal anti-inflammatory drugs such as ibuprofen work by inhibiting the enzyme cyclooxygenase (COX), which converts arachidonic acid to prostaglandin H2 (PGH2). PGH2, in turn, is converted by other enzymes to several other prostaglandins (which are mediators of pain, inflammation, and fever) and to thromboxane A2 (which stimulates platelet aggregation, leading to the formation of blood clots).

Like aspirin, indomethacin, and all other NSAIDs,[citation needed] ibuprofen is considered a nonselective COX inhibitor; that is, it inhibits two isoforms of cyclooxygenase, COX-1 and COX-2. The analgesic, antipyretic, and anti-inflammatory activity of NSAIDs appears to be achieved mainly through inhibition of COX-2, whereas inhibition of COX-1 would be responsible for unwanted effects on platelet aggregation and the gastrointestinal tract.[32] However, 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.[33]

In order to achieve the beneficial effects of ibuprofen and other NSAIDS without gastrointestinal ulceration and bleeding, selective COX-2 inhibitors were developed to inhibit the COX-2 isoform without inhibition of COX-1.[34]

Chemistry

Ibuprofen is only very slightly soluble in water. Less than 1 mg of ibuprofen dissolves in 1 ml water (< 1 mg/mL).[35]

Stereochemistry

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. As such, there are two possible enantiomers of ibuprofen, with the potential for different biological effects and metabolism for each enantiomer.

Indeed, the (S)-(+)-ibuprofen (dexibuprofen) was found to be the active form both in vitro and in vivo.

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 (alpha-methylacyl-CoA racemase), which converted (R)-ibuprofen to the active (S)-enantiomer.[36][37][38]

R-ibuprofen-B-2D-skeletal.png
S-ibuprofen-A-2D-skeletal.png
R-ibuprofen-A-2D-skeletal.png
S-ibuprofen-B-2D-skeletal.png
Ibuprofen-3D-balls.png
(S)-ibuprofen-3D-balls.png
(R)-ibuprofen
(S)-ibuprofen

Synthesis

The synthesis of this compound is a popular case study in green chemistry. The original Boots synthesis of ibuprofen consisted of six steps, started with the Friedel-Crafts acetylation of isobutylbenzene. Reaction with ethyl chloroacetate (Darzens reaction) gave the α,β-epoxy ester, which was hydrolyzed and decarboxylated to the aldehyde. Reaction with hydroxylamine gave the oxime, which was converted to the nitrile, then hydrolyzed to the desired acid:[39][40]

Boots synthesis of ibuprofen.png

An improved synthesis by BHC required only three steps. This improved synthesis won the Presidential Green Chemistry Challenge Greener Synthetic Pathways Award in 1997.[41]

After a similar acetylation, hydrogenation with Raney nickel gave the alcohol, which underwent palladium-catalyzed carbonylation:[39][42]

BHC synthesis of ibuprofen.png

History

Ibuprofen was derived from propionic acid by the research arm of Boots Group during the 1960s.[43] It was discovered by Andrew RM Dunlop, with colleagues Stewart Adams, John Nicholson, Vonleigh Simmons, Jeff Wilson 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. 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.[44]

Availability

A bottle of generic ibuprofen

Ibuprofen was made available under prescription in the United Kingdom in 1969, and in the United States in 1974.[citation needed] In the years since, the good tolerability profile, along with extensive experience in the population, as well as in so-called Phase IV trials (post-approval studies), has resulted in the availability of ibuprofen over the counter in pharmacies worldwide, as well as in supermarkets and other general retailers.[citation needed]

North America

Ibuprofen is commonly available in the United States up to the FDA's 200 mg 1984 dose limit OTC, higher by prescription.[9]

In Canada, the OTC dose limit is 400 mg.[citation needed]

In 2009, the first injectable formulation of ibuprofen was approved in the United States, under the trade name Caldolor.[45][46] Ibuprofen was the only parenteral for both pain and fever available in the country prior to the approval of Ofirmev (acetaminophen) injection by the FDA.[47]

Research

Ibuprofen is sometimes used for the treatment of acne, because of its anti-inflammatory properties,[48] and has been sold in Japan in topical form for adult acne.[49]

As with other NSAIDs, ibuprofen may be useful in the treatment of severe orthostatic hypotension (low blood pressure when standing up).[50]

In some studies, ibuprofen showed superior results compared to a placebo in the prophylaxis of Alzheimer's disease, when given in low doses over a long time.[51] 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 it. Aspirin, other NSAIDs, and paracetamol (acetaminophen) had no effect on the risk for Parkinson's.[52] In March 2011, researchers at Harvard Medical School announced in Neurology that ibuprofen had a neuroprotective effect against the risk of developing Parkinson's disease.[53][54][55] People regularly consuming ibuprofen were reported to have a 38% lower risk of developing Parkinson's disease, but no such effect was found for other pain relievers, such as aspirin and paracetamol. Use of ibuprofen to lower the risk of Parkinson's disease in the general population would not be problem-free, given the possibility of adverse effects on the urinary and digestive systems.[56] Further research is warranted before recommending ibuprofen for this use.

References

  1. ^ Van Esch, A; Van Steensel-Moll, HA; Steyerberg, EW; Offringa, M; Habbema, JD; Derksen-Lubsen, G (1995). "Antipyretic efficacy of ibuprofen and acetaminophen in children with febrile seizures". Archives of pediatrics & adolescent medicine 149 (6): 632–7. PMID 7767417.  edit
  2. ^ WHO Model List of Essential Medicines (16th ed.). World Health Organization (WHO). March 2009. http://www.who.int/entity/medicines/publications/essentialmedicines/Updated_sixteenth_adult_list_en.pdf. Retrieved 2011-03-30. 
  3. ^ WHO Model List of Essential Medicines for Children (2nd ed.). World Health Organization (WHO). March 2010. http://www.who.int/entity/medicines/publications/essentialmedicines/Updated_second_children_list_en.pdf. Retrieved 2011-03-30. 
  4. ^ Stuart MC, Kouimtzi M, Hill SR, ed (2009). WHO Model Formulary 2008 (2nd ed.). World Health Organization (WHO). ISBN 978-92-4-154765-9. http://whqlibdoc.who.int/publications/2009/9789241547659_eng.pdf. Retrieved 2011-03-30. 
  5. ^ WHO Model Formulary for Children 2010 (2nd ed.). World Health Organization (WHO). 2010. ISBN 978-92-4-159932-0. http://www.who.int/entity/selection_medicines/list/WMFc_2010.pdf. Retrieved 2011-03-30. 
  6. ^ Adams, S. S. (1992). "The propionic acids: A personal perspective". Journal of clinical pharmacology 32 (4): 317–323. PMID 1569234.  edit
  7. ^ "PubMed Health - Ibuprofen". U.S. National Library of Medicine. 2010-10-01. http://www.ncbi.nlm.nih.gov/pubmedhealth/PMH0000598. Retrieved 2011-01-20. 
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