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15687-27-1

15687-27-1 Structure

15687-27-1 Structure
IdentificationMore
[Name]

Ibuprofen
[CAS]

15687-27-1
[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
[EINECS(EC#)]

239-784-6
[Molecular Formula]

C13H18O2
[MDL Number]

MFCD00010393
[Molecular Weight]

206.28
[MOL File]

15687-27-1.mol
Chemical PropertiesBack Directory
[Appearance]

Colourless, Crystalline Solid
[mp ]

77-78 °C(lit.)
[bp ]

157 °C (4 mmHg)
[Stability:]

Stable. Combustible. Incompatible with strong oxidizing agents.
[Water Solubility ]

insoluble
[Usage]

A selective cyclooxygenase inhibitor (IC50=14.9uM). Inhibits PGH synthase-1 and PGH synthase-2 with comparable potency
[Merck ]

14,4881
[CAS DataBase Reference]

15687-27-1(CAS DataBase Reference)
[NIST Chemistry Reference]

Ibuprofen(15687-27-1)
[EPA Substance Registry System]

15687-27-1(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xn,N,T,F
[Risk Statements ]

R22:Harmful if swallowed.
R63:Possible risk of harm to the unborn child.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
[Safety Statements ]

S36:Wear suitable protective clothing .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S36/37:Wear suitable protective clothing and gloves .
[RIDADR ]

2811
[WGK Germany ]

3
[RTECS ]

MU6640000
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[HS Code ]

29163920
[Hazardous Substances Data]

15687-27-1(Hazardous Substances Data)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Etanol-->Aluminium chloride-->Acetyl chloride-->2,2-Dimethyl-1,3-propanediol-->Isobutylbenzene-->2-Chloropropionic acid
[Preparation Products]

Aminoprofen
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

2-(4-Isobutylphenyl)-propionic acid(15687-27-1).msds
Questions And AnswerBack Directory
[description]

Ibuprofen belongs to a non-steroidal anti-inflammatory analgesic. It 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. It, 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. It 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.
The Ibuprofen was co-discovered by Dr. Stewart Adams (later he becomes a professor and won the Medal of the British Empire) and his team including CoLinBurrows and Dr. John Nicholson. The aim of the initial study was to develop a "super aspirin" to obtain an alternative for the treatment of rheumatoid arthritis that is comparable to that of aspirin but with less serious adverse reactions. For other drugs such as phenylbutazone, it has a high risk of causing adrenal suppression and other adverse events such as gastrointestinal ulcers. Adams decided to look for a drug with good gastrointestinal resistance, which is particularly important for all non-steroidal anti-inflammatory drugs.
Phenyl acetate drugs have aroused people's interest. Although some of these drugs have been found to be at risk of causing ulcers based on the dog's test, Adams is aware of that this phenomenon may be due to a relatively long half-life of the drug clearance. In this class of drugs there is a compound – ibuprofen, which has a relatively short half-life, sustaining only 2 hours. Among the screened alternative drugs, although it is not the most effective, it is the most secure. In 1964, ibuprofen had become the most promising alternative to aspirin.
[Indications]

  • Alleviate the acute phase of various kinds of chronic arthritis such as rheumatoid arthritis, osteoarthritis, spondyloarthropathies, gouty arthritis and rheumatoid arthritis as well as persistent symptoms of joint swelling and pain. It can be used for the non-cause treatment and control of disease.
  • For the treatment of various kinds of non-joint soft tissue rheumatic pain, such as shoulder pain, tenosynovitis, bursitis, myalgia and post-exercise pain.
  • For the treatment of acute mild to moderate pain such as: post-surgery, post-trauma, post-strain, primary dysmenorrhea, toothache, headache and so on.
  • It has an antipyretic effect against the fever of adults and children.
[Used in Particular Diseases]

Acute Gouty Arthritis:
Dosage and Frequency: 800 mg four times a day
[Increase stroke risk]

Ibuprofen is one of the most commonly used non-prescription painkillers, commonly used in the treatment of arthritis, muscle pain, neuralgia, headache, migraine, toothache, dysmenorrhea or low back pain. A recent study published in the British Medical Journal found that people who have taken a large number of antipyretic drugs, ibuprofen, have a 3-fold increase in the risk of getting stroke or heart disease.
Researchers from the University of Berne in Switzerland reviewed 31 clinical trials involving more than 11.6 million patients. Patients were treated with one of seven common analgesics. The results showed that patients subjecting to long-term administration of large doses of ibuprofen not only have a risk of getting stroke increased by 3 times, but also have significantly increased risk of suffering heart attack and heart disease death. However, the study also showed that occasionally taking ibuprofen for the treatment of headache will not be dangerous. The study also found that commonly used analgesic diclofenac sodium also has a similar problem.
The study found a health risk associated with long-term use of ibuprofen, being similar to the anti-arthritis drug rofecoxib (Velcro), which was halted in 2004 due to safety concerns.
[Precautions]

1.For late pregnancy women, it can prolong the pregnancy, causing dystocia and prolonged pregnancy course. Pregnant women and lactating women should not administrate it.
2. Inhibition of platelet aggregation; it can extent the bleeding time. This effect will disappear at 24 hours after withdrawal of the drug.
3. It can increase the blood urea nitrogen and serum creatinine content, further reducing the creatinine clearance rate. The following circumstances should be used with caution:
  • Bronchial asthma can be aggravated after treatment.
  • Heart failure, high blood pressure; medication can cause water retention, edema.
  • Hemophilia or other hemorrhagic diseases (including coagulation disorders and platelet dysfunction); medication can cause prolonged bleeding time, increase the bleeding tendency.
  • Patients with a history of gastrointestinal ulcers are prone to get gastrointestinal side effects, including generating new ulcers.
  • Patients of renal dysfunction, after administration, can get increased renal adverse reactions, and even get renal failure.
  • During long-term medication, it should be regularly checked of blood phase and liver, kidney function.
[Drug Interactions]

  • Drinking or combination with other non-steroidal anti-inflammatory drugs can increase the gastrointestinal side effects, and have the risk of ulcers. Long-term combination with acetaminophen can increase the toxic side effects on the kidney.
  • Combination with aspirin or other salicylic acid drugs causes no increase in the efficacy, but cam cause gastrointestinal adverse reactions and increase of the bleeding tendency.
  • Combination with heparin, dicoumarol and other anticoagulants as well as platelet aggregation inhibitors has the risk for increasing bleeding.
  • Combination with furosemide can weaken the sodium excretion effect and antihypertensive effect.
  • Combination with verapamil and nifedipine can increase the plasma concentration of the product.
  • Ibuprofen can increase the plasma concentration of digoxin; pay attention to adjusting the dose of digoxin upon co-administration.
  • Ibuprofen can enhance the role of anti-diabetic drugs (including oral hypoglycemic agents).
  • The goods, when used in combination with antihypertensive drugs can affect the antihypertensive effect of the latter one.
  • Probenecid can reduce the excretion of the goods, increase the concentration of blood, thereby increasing the toxicity, so it is proper to reduce the dosage upon co-administration.
  • The goods can reduce the excretion of methotrexate, increase the blood concentration which can reach up to the level of poisoning, so the goods should not be used with medium or large doses of methotrexate.
[Side Effects]

  • Gastrointestinal symptoms include indigestion, stomach burning sensation, stomach pain and nausea as well as vomiting. This usually appears in 16% long-term administrators. These symptoms will disappear upon drug withdraw. In most cases, the patients can tolerate even without withdrawal. A small number (<1%) of patients can get gastric ulcer and gastrointestinal bleeding. This are also cases of perforation due to ulcer.
  • Neurological symptoms such as headache, lethargy and dizziness; Tinnitus (rare) appears in 1% to 3% of patients.
  • Renal insufficiency is rare, mostly occur in patients of potential kidney disease; but a small number of patients may obtain lower extremity edema.
  • Other rare symptoms also include rash, bronchial asthma attack, elevated liver enzymes and leukopenia.
  • During medication, there might be emergence of gastrointestinal bleeding, liver and kidney dysfunction, visual impairment, abnormal blood and allergic reactions, etc., that should be discontinued.
Spectrum DetailBack Directory
[Spectrum Detail]

Ibuprofen(15687-27-1) 1H NMR
Ibuprofen(15687-27-1) IR2
Ibuprofen(15687-27-1) IR1
Ibuprofen(15687-27-1) 13C NMR
Ibuprofen(15687-27-1) MS
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Ibuprofen, 99%(15687-27-1)
[Alfa Aesar]

4-Isobutyl-alpha-methylphenylacetic acid, 99%(15687-27-1)
[Sigma Aldrich]

15687-27-1(sigmaaldrich)
[TCI AMERICA]

2-(4-Isobutylphenyl)propionic Acid,>98.0%(GC)(T)(15687-27-1)
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