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CAS NO:15687-27-1
EC NO:239-784-6
Ibuprofen is a medication in the nonsteroidal anti-inflammatory drug (NSAID) class that is used for treating pain, fever, and inflammation. This includes painful menstrual periods, migraines, and rheumatoid arthritis.
Ibuprofen may also be used to close a patent ductus arteriosus in a premature baby.
Ibuprofen can be used by mouth or intravenously.
Ibuprofen typically begins working within an hour.
Common side effects include heartburn and a rash. Compared to other NSAIDs, it may have other side effects such as gastrointestinal bleeding.
Ibuprofen increases the risk of heart failure, kidney failure, and liver failure. At low doses, it does not appear to increase the risk of heart attack; however, at higher doses it may.
Ibuprofen can also worsen asthma.While it is unclear whether it is safe in early pregnancy,it appears to be harmful in later pregnancy and therefore is not recommended.Like other NSAIDs, it works by inhibiting the production of prostaglandins by decreasing the activity of the enzyme cyclooxygenase (COX).
Ibuprofen is a weaker anti-inflammatory agent than other NSAIDs.
Ibuprofen was discovered in 1961 by Stewart Adams and John Nicholson while working at Boots UK Limited and initially marketed as Brufen.
Ibuprofen is available under a number of trade names, including Nurofen, Advil and Motrin.
Ibuprofen was first marketed in 1969 in the United Kingdom and in 1974 in the United States.
Ibuprofen is on the World Health Organization's List of Essential Medicines.
Ibuprofen is available as a generic medication.In 2019, it was the 29th most commonly prescribed medication in the United States, with more than 21 million prescriptions.
Chemical and physical data
Formula C13H18O2
Molar mass 206.285 g·mol−1
3D model (JSmol)
Interactive image
Chirality Racemic mixture
Density 1.03 g/cm3
Melting point 75 to 78 °C (167 to 172 °F)
Boiling point 157 °C (315 °F) at 4 mmHg
Solubility in water 0.021 mg/mL (20 °C)
Medical uses
Ibuprofen is used primarily to treat fever (including post-vaccination fever), mild to moderate pain (including pain relief after surgery), painful menstruation, osteoarthritis, dental pain, headaches, and pain 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.
Ibuprofen is used for inflammatory diseases such as juvenile idiopathic arthritis and rheumatoid arthritis.
Ibuprofen is also used for pericarditis and patent ductus arteriosus.
If a patient is self-treating with over-the-counter Ibuprofen, it should not be taken for more than 10 days, unless the patient has spoken with his/her doctor.
Ibuprofen is useful as a nonsteroidal anti-inflammatory research chemical. Ibuprofen is reported to inhibit the netrophil-dependent edema response of rabbit skin to C5a/PGE23. NSAID that inhibits cyclooxygenase-1 and -2.
History
Ibuprofen was developed while searching for an alternative pain reliever to aspirin in the 1950s.
Ibuprofen and related compounds were synthesized in 1961 by Stewart Adams, John Nicholson, and Colin Burrows who were working for the Boots Pure Drug Company in Great Britain. Adams and Nicholson filed for a British patent on ibuprofen in 1962 and obtained the patent in 1964; subsequent patents were obtained in the United States. The patent of Adams and Nicholson was for the invention of phenylalkane derivatives of the form shown in Figure 49.1, where R1 could be various alkyl groups, R2 was hydrogen or methyl, and X was COOH or COOR, with R being alkyl or aminoalkyl groups. The first clinical trials for ibuprofen were started in 1966. Ibuprofen was introduced under the trade name Brufen in 1969 in Great Britain.
Ibuprofen was introduced in the United States in 1974. Ibuprofen was initially off ered by prescription, but it became available in over-the-counter medications in the 1980s.
Uses
Cyclo-oxygenase inhibitor; analgesic; anti-inflammatory.
Uses
A common goal in the development of pain and inflammation medicines has been the creation of compounds that have the ability to treat inflammation, fever, and pain without disrupting other physiological functions. General pain relievers, such as aspirin and ibuprofen, inhibit both COX-1 and COX-2. A medication's specificaction toward COX-1 versus COX-2 determines the potential for adverse side effects. Medications with greater specificity toward COX-1 will have greater potential for producing adverse side effects. By deactivating COX-1, nonselective pain relievers increase the chance of undesirable side effects, especially digestive problems such as stomach ulcers and gastrointestinal bleeding. COX-2 inhibitors, such as Vioxx and Celebrex, selectively deactivate COX-2 and do not aff ect COX-1 at prescribed dosages. COX-2 inhibitors are widely prescribed for arthritis and pain relief. In 2004, the Food and Drug Administration (FDA) announced that an increased risk of heart attack and stroke was associated with certain COX-2 inhibitors. This led to warning labels and voluntary removal of products from the market by drug producers; for example, Merck took Vioxx off the market in 2004. Although ibuprofen inhibits both COX-1 and COX-2, it has several times the specificity toward COX-2 compared to aspirin, producing fewer gastrointestinal side effects.
Uses
A selective cyclooxygenase inhibitor (IC50=14.9uM). Inhibits PGH synthase-1 and PGH synthase-2 with comparable potency
Uses
Antibiotic
Definition
ChEBI: A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-(2-methylpropyl)phenyl group.
General Description
Ibuprofen, 2-(4-isobutylphenyl)propionic acid (Motrin,Advil, Nuprin), was introduced into clinical practice followingextensive clinical trials.
Ibuprofen appears to have comparableefficacy to aspirin in the treatment of RA, but with a lowerincidence of side effects.
Ibuprofen has also been approved for usein the treatment of primary dysmenorrhea, which is thoughtto be caused by an excessive concentration of PGs and endoperoxides. However, a recent study indicates that concurrentuse of ibuprofen and aspirin may actually interferewith the cardioprotective effects of aspirin, at least in patientswith established cardiovascular disease. This is becauseibuprofen can reversibly bind to the platelet COX-1isozymes, thereby blocking aspirin’s ability to inhibit TXA2synthesis in platelets.
Pharmacokinetics
Ibuprofen is rapidly absorbed on oral administration, with peak plasma levels being generally attained within 2 hours and a duration of action of less than 6 hours. As with most of these acidic NSAIDs, ibuprofen (pKa = 4.4) is extensively bound to plasma proteins (99%) and will interact with other acidic drugs that are protein bound.
Clinical Use
Ibuprofen is indicated for the relief of the signs and symptoms of rheumatoid arthritis and osteoarthritis, the relief of mild to moderate pain, the reduction of fever, and the treatment of dysmenorrhea.
Ibuprofen belongs to a non-steroidal anti-inflammatory analgesic.
Ibuprofen has excellent anti-inflammatory, analgesic and antipyretic effect with less adverse reactions.
It has been widely used in the world, as the world's best-selling non-prescription drugs.
Ibuprofen together with aspirin and paracetamol are listed as the three key antipyretic analgesics products. In our country, it is mainly used in pain alleviation and anti-rheumatism, etc.
Ibuprofen has much less applications in the treatment of cold and fever compared with paracetamol and aspirin. There are a dozens of pharmaceutical companies qualified for production of ibuprofen in China. But the bulk of the domestic market sales of ibuprofen have been occupied by Tianjin Sino-US Company.
Ibuprofen is a commonly used nonsteroidal antiinflammatory (NSAID) drug which is available both by prescription and over-the-counter.
Ibuprofen is considered to be among the safest NSAIDs and is generally well tolerated but can, nevertheless, rarely cause clinically apparent and serious acute liver injury.
Ibuprofen is a monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-(2-methylpropyl)phenyl group.
Ibuprofen has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, a cyclooxygenase 2 inhibitor, a cyclooxygenase 1 inhibitor, an antipyretic, a xenobiotic, an environmental contaminant, a radical scavenger, a drug allergen and a geroprotector.
Ibuprofen derives from a propionic acid. It is a conjugate acid of an ibuprofen(1-).
Ibuprofen is a non-steroidal anti-inflammatory drug (NSAID) derived from propionic acid and it is considered the first of the propionics. The formula of ibuprofen is 2-(4-isobutylphenyl) propionic acid and its initial development was in 1960 while researching for a safer alternative for aspirin.
Ibuprofen was finally patented in 1961 and this drug was first launched against rheumatoid arthritis in the UK in 1969 and USA in 1974.
Ibuprofen was the first available over-the-counter NSAID. On the available products, ibuprofen is administered as a racemic mixture. Once administered, the R-enantiomer undergoes extensive interconversion to the S-enantiomer in vivo by the activity of the alpha-methylacyl-CoA racemase. In particular, it is generally proposed that the S-enantiomer is capable of eliciting stronger pharmacological activity than the R-enantiomer.
USES
Anti-inflammatory; analgesic; antipyretic
Anti-inflammatory
Ingredient in over-the-counter pain relievers
Indicated for both acute and long-term management of rheumatoid arthritis, osteoarthritis, and psoriatic arthritis.
About this substance
Helpful information
Ibuprofen is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, for intermediate use only.
Ibuprofen is used at industrial sites and in manufacturing.
Consumer Uses
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
Article service life
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment. ECHA has no public registered data indicating whether or into which articles the substance might have been processed.
Widespread uses by professional workers
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the types of manufacture using this substance. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
Formulation or re-packing
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
Uses at industrial sites
Ibuprofen has an industrial use resulting in manufacture of another substance (use of intermediates).
Ibuprofen is used for the manufacture of: chemicals.
Release to the environment of Ibuprofen can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates).
Manufacture
Release to the environment of Ibuprofen can occur from industrial use: manufacturing of the substance.
Ibuprofen is a frequently used over-the-counter drug for treating pain, inflammation, and fever.
Ibuprofen is a relatively simple molecule that was discovered and developed in the 1950s and 1960s at Boots Pure Drug in Nottingham, UK (now Boots UK in Beeston). The initial British patent on ibuprofen and a long list of similar compounds was awarded to John Nicholson and Stewart Adams of Boots in 1964.
The trivial name ibuprofen comes from fragments of its chemical name, (±)-2-(p-isobutylphenyl)propionic acid. As the (±) implies, the article of commerce is racemic. The images show the more biologically active (S)-enantiomer. Ibuprofen is sold under a large number of trade names; Advil and Motrin are the most common in the United States.
In addition to its common uses, ibuprofen has been used to treat inflammatory diseases such as rheumatoid and juvenile idiopathic arthritis. But it is not without its risks: patients with cardiovascular disease, hypertension, and gastrointestinal disorders are cautioned against taking it. Ibuprofen also is contraindicated when individuals consume alcohol or low-dose aspirin.
Ibuprofen is an NSAID and non-selective COX inhibitor used to treat mild-moderate pain, fever, and inflammation.
Ibuprofen is the most commonly used and prescribed NSAID.
Ibuprofen is very common over the counter medication widely used as an analgesic, anti-inflammatory and antipyretic.
The use of ibuprofen and its enantiomer Dexibuprofen in a racemic mix is common for the management of mild to moderate pain related to dysmenorrhea, headache, migraine, postoperative dental pain, spondylitis, osteoarthritis, rheumatoid arthritis, and soft tissue disorder.
Ibuprofen is very well absorbed orally and the peak serum concentration can be attained in 1 to 2 hours after extravascular administration. When ibuprofen is administered immediately after a meal there is a slight reduction in the absorption rate but there is no change in the extent of the absorption.
Product Specification
Melting Point:74.5 - 77.5 Deg C
Heavy metals:<10ppm
Loss on Drying:<0.5%
Purity:>98%
Residue on Ignition:<0.1%
Bulk density:0.20 - 0.50g/ml
Cl:<0.010%
Appearance:White crystalline powder
Ibuprofen (Advil) is a non-selective COX inhibitor with an IC50 of 0.33 mM.
Ibuprofen is known to have an antiplatelet effect, though Ibuprofen (Advil) is relatively mild and short-lived when compared with that of aspirin or other better-known antiplatelet agents.
Ibuprofen, indomethacin, and meclofenamate were potent inhibitors of the microsomal cyclooxygenase prepared from feline lung with IC50 of 0.33 mM, 29 μM, and 4.7 μM, respectively.
Ibuprofen is classified into a propionate derivative according to the chemical structure.The pharmacological actions of the propionate derivative are:
1. Ibuprofen lowers the elevated thermal set point in the thermoregulation center and thus lowers the temperature.
2. Ibuprofen relieves pain through its action on the hypothalamus.
3. Ibuprofen inhibits synthesis of prostaglandin and thus exerts antiinflammatory action.Major propionate derivatives; ibuprofen, ketoprofen, flurbiprofen Anti inflammatory, antipyretic, and analgesic effects (greater effects than aspirin).
Ibuprofen is an antipyretic anti-inflammatory drug (NSAID) used for arthritic, fever, as analges (pain automaton), specially to benefit from school aid to an incentive reinforced aid.
Ibuprofen is known to be an antiplatelet.
Function And Application
1.Ibuprofen is used to relieve pain, sharpness, and stiffness caused by osteoarthritis and rheumatoid arthritis.
2.Ibuprofen is used to be lightweight, also will pieces. over the counter
3.ibu aches and back pains Ibuprofen used for body health and light headaches from aches, muscle aches, arthritis, menstrual pains, aches and backaches.
Ibuprofen, mainly used in clinical arthritis, mild to moderate pain, dysmenorrhea, gout, etc. Aspirin gives light to the gastrointestinal tract.
Ibuprofen shows rheumatoid arthritis, rheumatoid arthritis, osteoarthritis, show is better in mobility and liking.
Ibuprofen for posterior cone disc herniation, lumbar cone stenosis, lumbar muscle tense, muscle fascia and sciatic nerve caused by various reasons Ibuprofen go back and forth and well, neck or nerve root type cervical cone disease, muscle fascia Side Get benefits and benefits, frozen shoulder and perfect.
IUPAC names
(+/-)-2-(4 ISOBUTYLPHENYL)-PROPIONIC ACID
(2RS)-2-[4-(2-Methylpropyl)phenyl]propanoic acid.
(2RS)-2-[4-(2-methylpropyl]phenyl]propanoic acid
(RS)-2-(4-(2-methylpropyl)phenyl)propanoic acid
(RS)-2-(4-isobutylphenyl)propanoic acid
(RS)-2-(4-Isobutylphenyl)propionsäure
.alpha.-methyl-4-(2-methylpropyl)-benzeneacetic acid
2(4-ISOBUTYLPHENYL)PROPIONIC ACID
2-(4-Isobutylphenyl)propanoic acid
2-(4-isobutylphenyl)propanoic acid
2-(4-Isobutylphenyl)propionic Acid
2-[4-(2-methylpropyl)phenil]propanoiv acid
2-[4-(2-methylpropyl)phenyl]propanoic acid
2-[4-(2-methylpropyl)phenyl]propanoic acid
4-Isobutyl-alpha-methylphenylacetic acid
alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid; 2-(4-Isobutylphenyl)-propionic acid; p-Isobutylhydratropic acid
Benzeneacetic acid, alpha-methyl-4-(2-methylpropyl)-
Benzeneacetic acid, α-methyl-4-(2-methylpropyl)-
benzeneacetic acid, α-methyl-4-(2-methylpropyl)-, chloride (1:1)
IBUPROFEN
Ibuprofen
ibuprofen
ibuprofen
SYNONYMS:
(+/-)-2-(4-ISOBUTYLPHENYL)-PROPIONIC ACID
2-(4-ISOBUTYLPHENYL)PROPIONIC ACID
4-ISOBUTYL-ALPHA-METHYLPHENYLACETIC ACID
AKOS NCG1-0060
(+/-)-ALPHA-METHYL-4-(2-METHYLPROPYL)-BENZENEACETIC ACID
ALPHA-METHYL-4-[2-METHYLPROPYL]BENZENEACETIC ACID
ALPHA-METHYL-4-(ISOBUTYL)PHENYLACETIC ACID
[A-METHYL-4-ISOBUTYL]PHENYLACETIC ACID
AURORA KA-7229
(+/-)-IBUPROFEN
IBUPROFEN
MOTRIN(TM)
RARECHEM AL BO 0989
(.+/-.)-2-(p-Isobutylphenyl)propionic acid
2-(4-isobutylphenyl)propanoicacid
2-(p-Isobutylphenyl)propionic acid
2-(p-isobutylphenyl)propionicacid
4-Isobutylhydratropic acid
4-isobutylhydratropicacid
Acide (isobutyl-4 phenyl)-2 propionique
