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Ibuprofen

From Wikipedia, the free encyclopedia
Nonsteroidal anti-inflammatory drug

Pharmaceutical compound
Ibuprofen
(R/S)-ibuprofen
(R)-ibuprofen
(R)-ibuprofen
Clinical data
Pronunciation/ˈaɪbjuːproʊfɛn/ ⓘ,/aɪbjuːˈproʊfən/,eye-bew-PROH-fən
Trade namesBrufen,others
Other namesIsobutylphenylpropionic acid
AHFS/Drugs.comMonograph
MedlinePlusa682159
License data
Pregnancy
category
Routes of
administration		By mouth,rectal,topical,intravenous
Drug classNonsteroidal anti-inflammatory drug (NSAID)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability80–100% (oral),[2] 87% (rectal)
Protein binding98%[3]
MetabolismLiver (CYP2C9)[3]
MetabolitesIbuprofen glucuronide, 2-hydroxyibuprofen, 3-hydroxyibuprofen, carboxy-ibuprofen, 1-hydroxyibuprofen
Onset of action30 minutes[4]
Eliminationhalf-life2–4 hours[5]
ExcretionUrine (95%)[3][6]
Identifiers
  • (RS)-2-(4-(2-Methylpropyl)phenyl)propanoic acid
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard(EPA)
ECHA InfoCard100.036.152Edit this at Wikidata
Chemical and physical data
FormulaC13H18O2
Molar mass206.285 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Density1.03 g/cm3
Melting point75 to 78 °C (167 to 172 °F)
Boiling point157 °C (315 °F) at 4 mmHg
Solubility in water0.021g/L
  • CC(C)Cc1ccc(cc1)[C@@H](C)C(=O)O
  • InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15) checkY
  • Key:HEFNNWSXXWATRW-UHFFFAOYSA-N checkY
  (verify)

Ibuprofen is anonsteroidal anti-inflammatory drug (NSAID) that is used to relievepain,fever, andinflammation.[7] This includespainful menstrual periods,migraines, andrheumatoid arthritis.[7] It can be takenorally (by mouth) orintravenously.[7] It typically begins working within an hour.[7]

Commonside effects includeheartburn,nausea,indigestion, andabdominal pain.[7] Potential side effects includegastrointestinal bleeding.[8] Long-term use has been associated withkidney failure, and rarelyliver failure, and it can exacerbate the condition of people withheart failure.[7] At low doses, it does not appear to increase the risk ofmyocardial infarction (heart attack); however, at higher doses it may.[8] Ibuprofen can also worsenasthma.[8] While its safety in earlypregnancy is unclear,[7] it appears to be harmful in later pregnancy, so it is not recommended during that period.[9] It works by inhibiting the production ofprostaglandins by decreasing the activity of the enzymecyclooxygenase (COX).[7] Ibuprofen is a weaker anti-inflammatory agent than other NSAIDs.[8]

Ibuprofen was discovered in 1961 byStewart Adams and John Nicholson[10] while working atBoots the Chemists and initially sold as Brufen.[11] It is available under a number of brand names includingAdvil,Brufen,Motrin, andNurofen.[7][12] Ibuprofen was first sold in 1969 in the United Kingdom and in 1974 in the United States.[7][11] It is on theWorld Health Organization's List of Essential Medicines.[13] It is available as ageneric medication.[7] In 2023, it was the 32nd most commonly prescribed medication in the United States, with more than 17 million prescriptions.[14][15]

Medical uses

[edit]
Example of some 200 mg ibuprofen tablets
A 150 ml bottle (100 mg/5 ml dosage) of ibuprofen, sold in Greece

Ibuprofen is used primarily to treatfever (including post-vaccination fever), mild to moderatepain (including pain relief aftersurgery),painful menstruation,osteoarthritis, dental pain,headaches, andpain 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.[16] A Cochrane medical review of 51 trials of NSAIDs for the treatment oflower back pain found that "NSAIDs are effective for short-term symptomatic relief in patients with acute low back pain".[17]

It is used for inflammatory diseases such asjuvenile idiopathic arthritis andrheumatoid arthritis.[18][19] It is also used forpericarditis and to close apatent ductus arteriosus in apremature baby.[20][7][21][22]

Ibuprofen lysine

[edit]

In some countries, ibuprofenlysine (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.[23] However, subsequent studies have shown no statistical differences between the lysine salt and standalone ibuprofen.[24][25]

In 2006, ibuprofen lysine was approved in the United States by theFood and Drug Administration (FDA) for closure of patent ductus arteriosus in premature infants weighing between 500 and 1,500 g (1 and 3 lb), who are no more than 32 weeks gestational age when usual medical management (such as fluid restriction, diuretics, and respiratory support) is not effective.[26]

Adverse effects

[edit]

Adverse effects includenausea,heartburn,indigestion,diarrhea,constipation,gastrointestinal ulceration,headache,dizziness, rash, salt and fluid retention, andhigh blood pressure.[7][19][27]

Infrequent adverse effects include esophageal ulceration,heart failure,high blood levels of potassium,kidney impairment, confusion, andbronchospasm.[19] Ibuprofen can exacerbate asthma, sometimes fatally.[28]

Allergic reactions, includinganaphylaxis, may occur.[29] 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. Amonograph relating ibuprofen plasma concentration, time since ingestion, and risk of developing renal toxicity in people who have overdosed has been published.[30]

In October 2020, the USFood and Drug Administration (FDA) required theprescribing information to be updated for all NSAID medications to describe the risk of kidney problems in unborn babies that result in low amniotic fluid.[31][32]

Cardiovascular risk

[edit]

Along with several other NSAIDs, chronic ibuprofen use is correlated with the risk of progression tohypertension in women, though less than forparacetamol (acetaminophen),[33] andmyocardial infarction (heart attack),[34] particularly among those chronically using higher doses. On 9 July 2015, the FDA toughened warnings of increasedheart attack andstroke risk associated with ibuprofen and related NSAIDs; the NSAIDaspirin is not included in this warning.[35] TheEuropean Medicines Agency (EMA) issued similar warnings in 2015.[36][37]

Skin

[edit]

Along with other NSAIDs, ibuprofen has been associated with the onset ofbullous pemphigoid or pemphigoid-like blistering.[38] As with other NSAIDs, ibuprofen has been reported to be aphotosensitizing agent,[39] but it is considered a weak photosensitizing agent compared to other members of the2-arylpropionic acid class. Like other NSAIDs, ibuprofen is an extremely rare cause of theautoimmune diseasesStevens–Johnson syndrome (SJS) andtoxic epidermal necrolysis.[40][41][42]

Pregnancy

[edit]

TheNational Health Service recommends against the use of ibuprofen for more than 3 days in pregnancy as it can affect the fetus' kidneys and circulatory system. Paracetamol is considered a safer alternative.[43]

A 2012 Canadian study of pregnant women suggested that those taking any type or amount of NSAIDs (including ibuprofen,diclofenac, andnaproxen) were 2.4 times more likely tomiscarry than those not taking the medications.[44] However, a 2014 Israeli study found no increased risk of miscarriage in the group of mothers using NSAIDs and noted that two previous studies, including the 2012 Canadian study, "did not adjust for important known risk factors" which may have exposed those results to residualconfounding.[45]

Interactions

[edit]

Alcohol

[edit]

Drinkingalcohol when taking ibuprofen may increase the risk ofstomach bleeding.[46]

Aspirin

[edit]

According to the FDA, "ibuprofen can interfere with theantiplatelet effect of low-doseaspirin, potentially rendering aspirin less effective when used forcardioprotection andstroke 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 8 hours or more for ibuprofen taken before IR aspirin. However, this timing cannot be recommended forenteric-coated aspirin. If ibuprofen is taken only occasionally without the recommended timing, though, the reduction of the cardioprotection and stroke prevention of a daily aspirin regimen is minimal.[47]

Paracetamol (acetaminophen)

[edit]

Ibuprofen combined withparacetamol is considered generally safe in children for short-term usage.[48]

Overdose

[edit]

Ibuprofen overdose has become common since it was licensed forover-the-counter (OTC) use. Many overdose experiences are reported in themedical literature, although the frequency of life-threatening complications from ibuprofen overdose is low.[49] Human responses in cases of overdose range from an absence of symptoms to a fatal outcome despite intensive-care treatment. Most symptoms are an excess of the pharmacological action of ibuprofen and include abdominal pain, nausea,vomiting, drowsiness, dizziness, headache,ear ringing, andnystagmus. Rarely, more severe symptoms such asgastrointestinal bleeding,seizures,metabolic acidosis,hyperkalemia,low blood pressure,slow heart rate,fast heart rate,atrial fibrillation,coma, liver dysfunction,acute kidney failure,cyanosis,respiratory depression, andcardiac arrest have been reported.[50] 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.

The correlation between the 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 adult male);[51] however, large doses do not indicate the clinical course is likely to be lethal.[52] A preciselethal dose is difficult to determine, as it may vary with age, weight, and concomitant conditions of the person.

Treatment to address an ibuprofen overdose is based on how the symptoms present. In cases presenting early, decontamination of the stomach is recommended. This is achieved usingactivated charcoal; charcoal absorbs the drug before it can enter thebloodstream.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.[53] Most ibuprofen ingestions produce only mild effects, and the management of overdose is straightforward. Standard measures to maintain normal urine output should be instituted andkidney function monitored.[51] 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, the kidneys' excretion of the unchanged drug is minimal. Forced alkaline diuresis is, therefore, of limited benefit.[54]

Pharmacology

[edit]

Ibuprofen works by inhibitingcyclooxygenase (COX) enzymes, which convertarachidonic acid toprostaglandin H2 (PGH2). PGH2, in turn, is converted by other enzymes into variousprostaglandins (which mediate pain,inflammation, and fever) andthromboxane A2 (which stimulatesplatelet aggregation and promotesblood clot formation).

Like aspirin andindomethacin, ibuprofen is a nonselective COX inhibitor, in that it inhibits twoisoforms of cyclooxygenase,COX-1 andCOX-2. Theanalgesic,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.[55] 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.[56]

IC50 of ibuprofen[57]
EnzymeIC50 [μM]
COX-113
COX-2370

Ibuprofen is administered as aracemic mixture. TheR-enantiomer undergoes extensive interconversion to theS-enantiomerin vivo. TheS-enantiomer is believed to be the more pharmacologically active enantiomer.[58] TheR-enantiomer is converted through a series of three main enzymes. These enzymes includeacyl-CoA-synthetase, which converts theR-enantiomer to (−)-R-ibuprofen I-CoA; 2-arylpropionyl-CoA epimerase, which converts (−)-R-ibuprofen I-CoA to (+)-S-ibuprofen I-CoA; and hydrolase, which converts (+)-S-ibuprofen I-CoA to theS-enantiomer.[42] In addition to the conversion of ibuprofen to theS-enantiomer, the body can metabolize ibuprofen to several other compounds, including numerous hydroxyl, carboxyl and glucuronyl metabolites. Virtually all of these have no pharmacological effects.[42]

Unlike most other NSAIDs, ibuprofen also acts as an inhibitor ofRho kinase and may be useful in recovery from spinal cord injury.[59][60] Another unusual activity is inhibition of the sweet taste receptor.[61]

Pharmacokinetics

[edit]

After oral administration,peak serum concentration is reached after 1–2 hours, and up to 99% of the drug isbound to plasma proteins.[62] The majority of ibuprofen is metabolized and eliminated within 24 hours in the urine; however, 1% of the unchanged drug is removed throughbiliary excretion.[58]

Metabolism

[edit]

Ibuprofen mainly undergoeshepatic metabolism. The following table shows potential pathways of ibuprofen metabolism. Both hydroxymetabolites and carboxyl-ibuprofen are inactive.[63]

Hepatic metabolism of ibuprofen[64][65][66]
Drug substrateOther substratesEnzymesProductsSide products
ibuprofenn/dn/d1-hydroxyibuprofen
ibuprofenoxygen, protons, NADPHCYP3A4,CYP2C19,CYP2C8,CYP2C92-hydroxyibuprofenNADP, water
ibuprofenoxygen, protons, NADPHCYP2C8, CYP2C9, CYP2C193-hydroxyibuprofenNADP, water
3-hydroxyibuprofenwater, oxygenCYP2C9carboxyl-ibuprofenhydrogen peroxide
ibuprofenuridine diphosphate glucuronic acidUDP-glucuronosyltransferase (1-1, 1-3, 1-9, 1-10, 2B4, 2B7)ibuprofen glucuronideuridine 5'-diphosphate

Chemistry

[edit]

Ibuprofen is practically insoluble in water, but very soluble in most organic solvents likeethanol (66.18 g/100 mL at 40 °C for 90% EtOH),methanol,acetone anddichloromethane.[67]

The original synthesis of ibuprofen by theBoots Group started with the compoundisobutylbenzene. The synthesis took six steps. Firstly, isobutylbenzene undergoesFriedel-Crafts acylation withacetic anhydride, yieldingp-isobuthylphenyl methylketone. Then, throughDarzens reaction withethyl chloroacetate, a α,β-epoxyester is obtained. Then, in acidic environment, it undergoesdecarboxylation andhydrolysis, yielding analdehyde bearing one more carbon atom than the initial ketone. Then, it goes through a reaction withhydroxylamine, yielding a correspondingoxime. Later, it is converted into anitrile and hydrolyzed into ibuprofen.[68]

Boots synthesis of ibuprofen


A modern,greener technique with fewer waste byproducts (23% of total product mass vs. 60% theoretical value) for the synthesis involves only three steps and was developed in the 1980s by theCelanese Chemical Company.[69][70] The synthesis is initiated with the acylation of isobutylbenzene using the recyclableLewis acid catalysthydrogen fluoride.[71][72] The followingcatalytic hydrogenation of isobutylacetophenone is performed with eitherRaney nickel orpalladium on carbon to lead into the key-step, thecarbonylation of 1-(4-isobutylphenyl)ethanol. This is achieved by aPdCl2(PPh3)2 catalyst, at around 50 bar of CO pressure, in the presence of HCl (10%).[73] The reaction presumably proceeds through the intermediacy of thestyrene derivative (acidic elimination of the alcohol) and (1-chloroethyl)benzene derivative (Markovnikow addition of HCl to the double bond).[74]

Modern synthesis of ibuprofen
Modern synthesis of ibuprofen

Stereochemistry

[edit]
(R)-ibuprofen(S)-ibuprofen

Ibuprofen, like other2-arylpropionate derivatives such asketoprofen,flurbiprofen andnaproxen, contains astereocenter in the α-position of thepropionate moiety. The product sold in pharmacies is aracemic mixture of theS andR-isomers. TheS (dextrorotatory) isomer is the more biologically active; this isomer has been isolated and used medically (seedexibuprofen for details).[67]

Theisomerase enzyme,alpha-methylacyl-CoA racemase, converts (R)-ibuprofen into the (S)-enantiomer.[75][76][77]

(S)-ibuprofen, theeutomer, harbors the desired therapeutic activity. The inactive (R)-enantiomer, thedistomer, undergoes a unidirectionalchiral inversion to offer the active (S)-enantiomer. That is, when the ibuprofen is administered as a racemate the distomer is convertedin vivo into the eutomer while the latter is unaffected.[78][79][80]

History

[edit]
TheRoyal Society of Chemistry blue plaque atBioCity Nottingham

Ibuprofen was derived frompropionic acid by theresearch arm ofBoots Group during the 1960s.[81] The name is derived from the 3 functional groups: isobutyl (ibu) propionic acid (pro) phenyl (fen).[82] Its discovery was the result of research during the 1950s and 1960s to find a safer alternative toaspirin.[11][83] The molecule was discovered and synthesized by a team led byStewart Adams, with a patent application filed in 1961.[11] Adams initially tested the drug as treatment for hishangover.[84] In 1985, Boots's worldwide patent for ibuprofen expired and generic products were launched.[85]

The medication was launched as a treatment forrheumatoid arthritis in the United Kingdom in 1969, and in the United States in 1974. Later, in 1983 and 1984, it became the first NSAID (other than aspirin) to be availableover-the-counter (OTC) in these two countries.[11][83] Boots was awarded theQueen's Award for Technical Achievement in 1985 for the development of the drug.[86]

In November 2013, work on ibuprofen was recognized by the erection of aRoyal Society of Chemistry blue plaque at Boots' Beeston Factory site in Nottingham,[87] which reads:

In recognition of the work during the 1980s by The Boots Company PLC on the development of ibuprofen which resulted in its move from prescription-only status to over-the-counter sale, therefore expanding its use to millions of people worldwide

and another atBioCity Nottingham, the site of the original laboratory,[87] which reads:

In recognition of the pioneering research work, here on Pennyfoot Street, by Dr Stewart Adams and Dr John Nicholson in the Research Department of Boots which led to the discovery of ibuprofen used by millions worldwide for the relief of pain.

Availability and administration

[edit]
See also:Ibuprofen brand names
A bottle of generic ibuprofen

Ibuprofen was made available by prescription in the United Kingdom in 1969 and in the United States in 1974.[88]

Ibuprofen is theinternational nonproprietary name (INN),British Approved Name (BAN),Australian Approved Name (AAN) andUnited States Adopted Name (USAN). In the United States, it has been sold under the brand-names Motrin and Advil since 1974[89] and 1984,[90] respectively.

In 2009, the first injectable formulation of ibuprofen was approved in the United States, under the brand name Caldolor.[91][92]

Ibuprofen can be takenorally (by mouth) andintravenously.[7]

Research

[edit]

Ibuprofen is sometimes used for the treatment ofacne because of itsanti-inflammatory properties, and has been sold in Japan in topical form for adult acne.[93][94] As with other NSAIDs, ibuprofen may be useful in the treatment of severeorthostatic hypotension (low blood pressure when standing up).[95] NSAIDs are of unclear utility in the prevention and treatment ofAlzheimer's disease.[96][97]

Ibuprofen has been associated with a lower risk ofParkinson's disease and may delay or prevent it.Aspirin, other NSAIDs, andparacetamol (acetaminophen) had no effect on the risk for Parkinson's.[98] In March 2011, researchers atHarvard Medical School announced that ibuprofen had aneuroprotective effect against the risk of developingParkinson's disease.[99][100][101] 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.[102]

Somedietary supplements might be dangerous to take along with ibuprofen and other NSAIDs, but as of 2016[update], more research needs to be conducted to be certain. These supplements include those that canprevent platelet aggregation, includingginkgo,garlic,ginger,bilberry,dong quai,feverfew,ginseng,turmeric,meadowsweet (Filipendula ulmaria), andwillow (Salix spp.); those that containcoumarin, includingchamomile,horse chestnut,fenugreek andred clover; and those that increase the risk of bleeding, liketamarind.[103]

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[edit]
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