ibuprofen
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ibuprofen
IbuprofenSystematic (IUPAC) name2-propanoic acidIdentifiersCAS number15687-27-1ATC codeM01AE01PubChem3672DrugBankAPRD00372ChemSpider3544Chemical dataFormulaC13H18O2 Mol. mass206.28SMILESeMolecules & PubChemPhysical dataMelt. point76 °C (169 °F)Pharmacokinetic dataBioavailability49–73%Protein binding99%MetabolismHepatic (CYP2C9)Half life1.8–2 hoursExcretionRenalTherapeutic considerationsLicence dataUSPregnancy cat.C(AU) D(US)Legal statusUnscheduled(AU) GSL(UK) OTC(US)RoutesOral, rectal and topicalIbuprofen (INN) (IPA: /ˌaɪbjuːˈpɹəʊfɛn/) (from the now outdated nomenclature iso-butyl-propanoic-phenolic acid) is a non-steroidal anti-inflammatory drug (NSAID) originally marketed as Brufen, and since then under various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 Nurofen, 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 with 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.// HistoryIbuprofen was developed by the research arm of Boots Group during the 1960s. It was discovered by Stewart Adams, with colleagues John Nicholson, Jeff Bruce Wilson, Andrew RM Dunlop 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. Typical administrationLow 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.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. Off-label and investigational useAs with other NSAIDs, ibuprofen may be useful in the treatment of severe orthostatic hypotension.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. 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. Further research is warranted before recommending ibuprofen for this use. Ibuprofen lysineIn 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 has been shown to have a more rapid onset of action compared to acid ibuprofen.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. With regard to this indication, ibuprofen lysine is an effective alternative to intravenous indomethacin and may be advantageous in terms of renal function. Mechanism of actionIbuprofen 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. Adverse effectsIbuprofen 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.Common adverse effects include: nausea, dyspepsia, gastrointestinal ulceration/bleeding, raised liver enzymes, diarrhea, epistaxis, headache, dizziness, unexplained rash, salt and fluid retention, and hypertension.Infrequent adverse effects include: oesophageal ulceration, heart failure, hyperkalaemia, renal impairment, confusion, bronchospasm, and rash.Very infrequent adverse effects include Stevens-Johnson syndrome. PhotosensitivityAs with other NSAIDs, ibuprofen has been reported to be a photosensitising agent. 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. Cardiovascular riskAlong with several other NSAIDs, ibuprofen has been implicated in elevating the risk of myocardial infarction, particularly among those chronically using high doses. Risks in pregnancyTwo studies have found an increased risk of miscarriage with the use of NSAIDs such as ibuprofen early in pregnancy; however, several other studies did not find this association. 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.When ibuprofen is used as directed, 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.Of the two enantiomers of ibuprofen, only (R)-ibuprofen is teratogenic (especially in the first trimester). Over-the-counter (OTC) ibuprofen contains a 50-50 mixture of the (R) and (S) isomers, and hence is not recommended for use during pregnancy. The pure (S) isomer is not widely available due to the cost and difficulty of production. Risks in Inflammatory Bowel Disease (IBD)Ibuprofen should not be used regularly 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. StereochemistryIbuprofen, 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.Indeed it was found that (S)-(+)-ibuprofen (dexibuprofen) was 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 (2-arylpropionyl-CoA epimerase) which converted (R)-ibuprofen to the active (S)-enantiomer. Thus, due to the expense and futility that might be involved in making a pure enantiomer, most ibuprofen formulations currently marketed are racemic mixtures.(R)-ibuprofen(S)-ibuprofen Water SolubilityIbuprofen is only very slightly soluble in water, less than 1mg of Ibuprofen dissolves in 1ml water (< 1 mg/mL). Human toxicologyIbuprofen 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. 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. The severity of symptoms varies with t
Taking ibuprofen and aspirin can have a negative impact on your next prostate cancer screening.Scientists are concerned with the long-term consequences of so many prescription drugs � and over-the-counter medicines like acetaminophen and ibuprofen � in drinking water. . Aspirin cut the risk by 13%, while ibuprofen lowered it by a fifth. These drugs also make it harder to detect humors, a Reuters report indicates.Regular use of common painkillers such as aspirin and ibuprofen reduces the risk of breast cancer, according to an international study. He had to wait over 15 minutes for a wheelchair, and then the medical staff at the water park treated him more or less the way a school nurse would treat someoneâwith a brochure, some water, and some ibuprofen. *Caution* men shouldn't take the painkillers in an effort to prevent prostate cancer just yet. There are a few more that may surprise you, like aspirin, acetaminophen, and ibuprofen, and certain household plants. Week 1 proved that it doesn't take long to get bruised and battered in the NFL. A new study(1) published on BMJ.Drink lots of water to prevent dehydration,get plenty of sleep,Avoid alcohol,take acetaminophen or ibuprofen to relieve
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ibuprofen
Ibuprofen (IPA: /ˌaɪbjuːˈpɹəʊfɛn/) (from the now outdated nomenclature i so-bu tyl-pro panoic-phen olic acid) is a non-steroidal anti-inflammatory drug (NSAID) originally ...
Ibuprofen - Wikipedia, the free encyclopedia
Explains the medication ibuprofen (Advil, Motrin, Nuprin, Medipren) a drug used for the management of mild to moderate pain, fever, and inflammation. Article includes descriptions ...
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MedlinePlus Drug Information: Ibuprofen
Ibuprofen (Advil, Motrin) treats minor aches and pains caused by the common cold, headaches, toothaches, back or muscle aches. Includes ibuprofen side effects, interactions and ...
Ibuprofen Information from Drugs.com
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