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Ibuprofen{| border="1" cellpadding="2" cellspacing="0" width="275px" align="right" |bgcolor="#ffffff" align="center" colspan="2"| ''Ibuprofen'' |- |bgcolor="#ffffff" align="center" colspan="2"| ''2-(p-isobutylphenyl)propionic acid'' |- |bgcolor="#efefef"|Empirical formula |bgcolor="#dfefff"|C13H18O2 |- |bgcolor="#efefef"|Molecular weight |bgcolor="#dfefff"|206.3 |- |bgcolor="#efefef"|Bioavailability (Oral) |bgcolor="#dfefff"|''unknown'' |- |bgcolor="#efefef"|Metabolism |bgcolor="#dfefff"|hepatic |- |bgcolor="#efefef"|half life |bgcolor="#dfefff"|1.9-2.2 hours |- |bgcolor="#efefef"|Excretion |bgcolor="#dfefff"|renal |- |bgcolor="#efefef"|Pregnancy category (pharmaceutical) |bgcolor="#dfefff"|C (Australia) |} Ibuprofen is a NSAID (NSAID) used to relieve the symptoms of arthritis, primary dysmenorrhoea, fever; and as an analgesic, especially where there is an inflamation component. Ibuprofen was developed by the research arm of Boots the Chemists. It is widely marketed under various trademarks including Act-3, Advil, Brufen, Motrin, Nuprin, and Nurofen. ==Indications== Approved clinical indications for ibuprofen include: *rheumatoid arthritis *osteoarthritis *juvenile rheumatoid arthritis *primary dysmenorrhoea *fever *relief of acute and/or chronic pain states in which there is an inflammatory component Ibuprofen is widely used for the relief of headache including migraine. It is also widely ''marketed'' as an analgesic agent (rather than as an NSAID) and is often used for general pain conditions including those that arise from various injuries (such as sporting injuries), illnesses (such as influenza, shingles, gout), and post-operative pain. As with other NSAIDs, ibuprofen inhibits platelet aggregation, but is not used therapeutically for this action since it is a minor and reversible effect. ==Mechanism of action== Ibuprofen is an NSAID and, as such, is believed to work through inhibition of cyclooxygenase (COX); thus inhibiting prostaglandin synthesis. ''Main article: Non-steroidal anti-inflammatory drug'' ==Adverse effects== 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 labelled to advise a maximum daily dose of 1.2 grams. ''Main article: Non-steroidal anti-inflammatory drug'' ===Reported ADRs=== Common adverse effects include: nausea, dyspepsia, gastrointestinal ulceration/bleeding, raised liver enzymes, diarrhoea, headache, dizziness, salt and fluid retention, hypertension (Rossi, 2004). Infrequent adverse effects include: oesophageal ulceration, heart failure, hyperkalaemia, renal impairment, confusion, bronchospasm, rash (Rossi, 2004) ===Photosensitivity=== As with other NSAIDs, ibuprofen has been reported to be a photosensitivity agent. (Castell ''et al''., 1987) Ibuprofen, however, has a very weak absorption spectrum which does not reach into the solar spectrum. The molecule contains only a single phenyl moiety, and no bond conjugation, resulting in a very weak chromophore system. Ibuprofen, therefore, is only a very weak photosensitising agent when compared with other members of the 2-arylpropionic acids. ===Heart attack risk=== Along with several other NSAIDs, ibuprofen has been implicated in elevating the risk of myocardial infarction, particularly among those chronically using high doses. (Hippisley-Cox, 2005) ==Stereochemistry== Ibuprofen, like other 2-arylpropionate derivatives (including ketoprofen, flurbiprofen, naproxen, ''etc'') contains a chiral carbon in the β-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 it was found that ''S''-ibuprofen (sinisteribuprofen) was the active form both ''in vitro'' and ''in vivo''. Logically then, 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 which converted ''R''-ibuprofen to the active ''S''-enantiomer. Thus, due to the expense and futility that might be involved in marketing the single-enantiomer, all ibuprofen formulations currently marketed are a racemic mixture of both enantiomers. ==Availability== Ibuprofen was made available under prescription in the United Kingdom in 1969. In the years since, the good tolerability profile along with extensive experience in the community (otherwise known as clinical trial), has resulted in the rescheduling of small packs of ibuprofen to allow availability over-the-counter in pharmacies worldwide. Indeed there has been an increasing trend towards descheduling ibuprofen such that it is now available in supermarkets and other general retailers; in fact, in the United States, ibuprofen (most commonly in a 200mg dosage) is about as widely used as aspirin and acetaminophen as an over-the-counter painkiller. ==References== * Rossi S (Ed.) (2004). ''Australian Medicines Handbook 2004''. Adelaide: Australian Medicines Handbook. ISBN 0-9578521-4-2. * Castell JV, Gomez MJ, Miranda MA, Morera IM (1987). Photolytic degradation of ibuprofen. Toxicity of the isolated photoproducts on fibroblasts and erythrocytes. ''Photochem Photobiol'' 46 (6), 991-6. * Hippisley-Cox J, Coupland C (2005). Risk of myocardial infarction in patients taking cyclo-oxygenase-2 inhibitors or conventional non-steroidal anti-inflammatory drugs: population based nested case-control analysis. ''British Medical Journal'' 2005;330:1366 (11 June). Non-steroidal anti-inflammatory drugs Over-the-counter substances ms:Ibuprofen IbuprofenDoes anyone know the history of Ibuprofen? How it was discovered, when and by whom? See other meanings of words starting from letter: IIA | IB | IC | ID | IE | IF | IG | IH | IJ | IK | IL | IM | IN | IO | IP | IR | IS | IT | IU | IW | IX | IY | IZ |Words begining with Ibuprofen: Ibuprofen Ibuprofen Ibuprofen_potassium |
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