3D Mol Similar

Ibuprofen

: Iupac Name：2-[4-(2-methylpropyl)phenyl]propanoic acid; CAS No.: 15687-27-1; Molecular Weight：206.28082; Modify Date.: 2022-11-11 00:32; Introduction: 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. View more+

Request For Quotation

1. Names and Identifiers

: 1.1 Name; Ibuprofen; 1.2 Synonyms; (±)-ibuprofen (+/-)-2-(4-ISOBUTYLPHENYL)-PROPIONIC ACID (+/-)-ALPHA-METHYL-4-(2-METHYLPROPYL)-BENZENEACETIC ACID (RS)-ibuprofen [A-METHYL-4-ISOBUTYL]PHENYLACETIC ACID 2-(4-Isobutylphenyl)propanoic acid 2-(4-ISOBUTYLPHENYL)PROPIONIC ACID 4-ISOBUTYL-ALPHA-METHYLPHENYLACETIC ACID 4-Isobutyl-α-methylphenylacetic Acid Adran Advil AKOS NCG1-0060 ALPHA-METHYL-4-(ISOBUTYL)PHENYLACETIC ACID ALPHA-METHYL-4-[2-METHYLPROPYL]BENZENEACETIC ACID Amibufen Andran Benzeneacetic acid, α-methyl-4-(2-methylpropyl)- Bluton Brufen Dolgin Dolgirid Dolgit Dolo-Dolgit EINECS 239-784-6 Femadon fenbid IbU Ibumetin Ibutid Inoven IP-82 Lebrufen MFCD00010393 MOTRIN Novogent N Nurofen Panafen Para-Isobutylhydratropic Acid QVY1&R D1Y1&1 Racemic ibuprofen rufen rufin Seclodin UNII:WK2XYI10QM; View all

1.3 CAS No.: 15687-27-1

1.4 CID: 3672

1.5 EINECS(EC#): 239-784-6

1.6 Molecular Formula: C13H18O2 (isomer)

1.7 Inchi: 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)

1.8 InChIkey: HEFNNWSXXWATRW-UHFFFAOYSA-N

1.9 Canonical Smiles: CC(C)CC1=CC=C(C=C1)C(C)C(=O)O

1.10 Isomers Smiles: CC(C)CC1=CC=C(C=C1)C(C)C(=O)O

2. Properties

2.1 Density: 1.029

2.1 Melting point: 75-78℃

2.1 Boiling point: 157℃ (4 mmHg)

2.1 Refractive index: 1.5500 (estimate)

2.1 Flash Point: 216.7 °C

2.1 Precise Quality: 206.13100

2.1 PSA: 37.30000

2.1 logP: 3.07320

2.1 Appearance: Colourless, Crystalline Solid

2.2 Storage: Ambient temperatures.

2.3 Chemical Properties: Colourless, Crystalline Solid

2.4 Color/Form: White to Yellow Solid

2.5 Decomposition: When heated to decomposition it emits acrid smoke and fumes.

2.6 Odor: Characteristic odor

2.7 pKa: pKa 4.45± 0.04(H2O,t = 25±0.5,I=0.15(KCl))(Approximate)

2.8 Water Solubility: insoluble

2.9 Stability: Stable. Combustible. Incompatible with strong oxidizing agents.

2.10 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 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.

3.2 History: Ibuprofenwas developed while searching for an alternative pain reliever to aspirin in the 1950s. It andrelated compounds were synthesized in 1961 by Stewart Adams, John Nicholson, and ColinBurrows who were working for the Boots Pure Drug Company in Great Britain. Adams andNicholson 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 Nicholsonwas for the invention of phenylalkane derivatives of the form shown in Figure 49.1, whereR1 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 in1966. Ibuprofen was introduced under the trade name Brufen in 1969 in Great Britain. It wasintroduced in the United States in 1974. Ibuprofen was initially off ered by prescription, butit became available in over-the-counter medications in the 1980s.

3.3 Usage: 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.; View all

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: R22;R51/53;R63

4.1 Safety Statements: S36/37;S61

4.1 Packing Group: III

4.1 Octanol/Water Partition Coefficient: log Kow= 3.97

4.2 Hazard Class: 6.1(b)

4.2 Hazard Declaration: H302

4.2 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

4.3 RIDADR: 2811

4.3 Caution Statement: P301 + P312 + P330

4.3 Formulations/Preparations: Generic. Tablets 200 (nonprescription), 300, 400, 600, and 800 mg. Advil (Whitehall), Medipren (McNeil), Midol 200 (Glenbrook), Nuprin (Bristol-Myers). Tablets 200 mg (nonprescription). Children's Advil Suspension (Whitehall), Pedia-Profen (McNeil). Suspension 100 mg/5 ml. Motrin (Upjohn). Tablets 200 (Motrin IB, nonprescription), 300, 400 600, and 800 mg. Rufen (Boots). Tablets 400, 600, and 800 mg.

4.4 WGK Germany: 3

4.4 RTECS: MU6640000

4.4 Safety: Hazard Codes:?Xn,N
Risk Statements: 22-63-51/53
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: 61-36/37
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

4.5 Specification: ? Ibuprofen (CAS NO.15687-27-1), its Synonyms are (+-)-2-(p-Isobutylphenyl)propionic acid ; (+-)-Ibuprofen ; (+-)-alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid ; (+-)-p-Isobutylhydratropic acid ; (4-Isobutylphenyl)-alpha-methylacetic acid ; Acide (isobutyl-4-phenyl)-2 propionique ; Benzeneacetic acid, alpha-methyl-4-(2-methylpropyl)- ; p-Isobutyl-2-phenylpropionic acid .

4.6 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
child	LDLo	oral	469mg/kg (469mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Annals of Emergency Medicine. Vol. 15, Pg. 1308, 1986.
child	TDLo	oral	480mg/kg/17D- (480mg/kg)	LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"	Journal of Pediatrics. Vol. 90, Pg. 657, 1977.
child	TDLo	oral	500mg/kg (500mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"	Annals of Pharmacotherpy. Vol. 31, Pg. 432, 1997.
guinea pig	LD50	oral	495mg/kg (495mg/kg)	?	Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
hamster	LD50	oral	1690mg/kg (1690mg/kg)	?	Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
mammal (species unspecified)	LD50	oral	1gm/kg (1000mg/kg)	?	Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 42, Pg. 545, 1985.
man	LDLo	oral	171mg/kg (171mg/kg)	BEHAVIORAL: GENERAL ANESTHETIC VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION	British Medical Journal. Vol. 281, Pg. 1458, 1980.
man	TDLo	oral	120mg/kg/W-I (120mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	New York State Journal of Medicine. Vol. 78, Pg. 1239, 1978.
man	TDLo	oral	180mg/kg/3W-I (180mg/kg)	LIVER: "JAUNDICE, CHOLESTATIC"	American Journal of Gastroenterology. Vol. 91, Pg. 1626, 1996.
man	TDLo	oral	429mg/kg (429mg/kg)	LUNGS, THORAX, OR RESPIRATION: RESPIRATORY OBSTRUCTION KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"	Journal of Toxicology, Clinical Toxicology. Vol. 32, Pg. 315, 1994.
man	TDLo	oral	800mg/kg (800mg/kg)	BEHAVIORAL: COMA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Postgraduate Medical Journal. Vol. 69, Pg. 575, 1993.
man	TDLo	oral	1028mg/kg (1028mg/kg)	KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"	American Journal of Emergency Medicine. Vol. 13, Pg. 375, 1995.
mouse	LD50	intraperitoneal	320mg/kg (320mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH	Toxicology and Applied Pharmacology. Vol. 15, Pg. 310, 1969. Link to PubMed
mouse	LD50	oral	740mg/kg (740mg/kg)	BEHAVIORAL: ANALGESIA	Pharmaceutical Chemistry Journal Vol. 14, Pg. 119, 1980.
mouse	LD50	rectal	620mg/kg (620mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)	Oyo Yakuri. Pharmacometrics. Vol. 24, Pg. 415, 1982.
mouse	LD50	subcutaneous	395mg/kg (395mg/kg)	?	Oyo Yakuri. Pharmacometrics. Vol. 24, Pg. 415, 1982.
rabbit	LD50	oral	1400mg/kg (1400mg/kg)	?	Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 32, Pg. 1032, 1990.
rabbit	LD50	rectal	830mg/kg (830mg/kg)	?	Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 32, Pg. 1032, 1990.
rat	LD50	intraperitoneal	626mg/kg (626mg/kg)	BEHAVIORAL: ANALGESIA	Arzneimittel-Forschung. Drug Research. Vol. 27, Pg. 1006, 1977.
rat	LD50	oral	636mg/kg (636mg/kg)	?	Arzneimittel-Forschung. Drug Research. Vol. 34, Pg. 280, 1984.
rat	LD50	rectal	530mg/kg (530mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)	Oyo Yakuri. Pharmacometrics. Vol. 24, Pg. 415, 1982.
rat	LD50	subcutaneous	740mg/kg (740mg/kg)	?	Oyo Yakuri. Pharmacometrics. Vol. 24, Pg. 415, 1982.
women	TDLo	oral	8mg/kg (8mg/kg)	BEHAVIORAL: HEADACHE	JAMA, Journal of the American Medical Association. Vol. 239, Pg. 1062, 1978.
women	TDLo	oral	132mg/kg/6D-I (132mg/kg)	BLOOD: THROMBOCYTOPENIA	British Journal of Clinical Practice. Vol. 48, Pg. 51, 1994.
women	TDLo	unreported	96mg/kg/3D-I (96mg/kg)	SENSE ORGANS AND SPECIAL SENSES: DIPLOPIA: EYE	JAMA, Journal of the American Medical Association. Vol. 248, Pg

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin mild irritation, Category 3

Eye irritation, Category 2A

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H316 Causes mild skin irritation H320 Causes eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P332+P313 If skin irritation occurs: Get medical advice/attention. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 400 MHz in CDCl3

IR : KBr disc

IR : nujol mull

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

15687-27-1Total: 123 Synthesis Route

622-96-8 43 Suppliers

15687-27-1 504 Suppliers

Literatures:
Tetrahedron Letters, , vol. 32, # 28 p. 3369 - 3370
Yield: null

106-42-3 130 Suppliers

15687-27-1 504 Suppliers

Literatures:
Tetrahedron Letters, , vol. 32, # 28 p. 3369 - 3370
Yield: null

589-87-7 267 Suppliers

15687-27-1 504 Suppliers

Literatures:
Tetrahedron, , vol. 70, # 7 p. 1508 - 1515
Yield: null

View all

8. Precursor and Product

precursor:

64622-31-7

75560-80-4

63367-12-4

106-42-3

68064-52-8

4167-74-2

58609-73-7

60057-62-7

5161-04-6

61566-34-5

622-96-8

6448-14-2

2039-82-9

6448-10-8

51146-56-6

64622-20-4

92978-26-2

58142-30-6

41283-72-1

538-93-2

589-87-7

36039-36-8

67174-35-0

1553-60-2

51407-46-6

View all

product :

100319-40-2

61566-34-5

31121-93-4

6448-14-2

65813-55-0

75626-01-6

51146-56-6

51146-57-7

75626-00-5

42482-20-2

95499-72-2

41283-72-1

127222-69-9

3380-34-5

75625-99-9

110467-58-8

75625-98-8

36039-36-8

38861-78-8

60057-62-7

1117-74-4

51407-46-6

51146-55-5

40150-92-3

View all

9. Other Information

9.0 Merck: 14,4881

9.1 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.

9.2 Used in Particular Diseases: Acute Gouty Arthritis:
Dosage and Frequency: 800 mg four times a day

9.3 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.; View all

9.4 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.

View all

9.5 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.

View all

9.6 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.

View all

9.7 Chemical Properties: Colourless, Crystalline Solid

9.8 Uses: A selective cyclooxygenase inhibitor (IC50=14.9uM). Inhibits PGH synthase-1 and PGH synthase-2 with comparable potency

9.9 Uses: Cyclo-oxygenase inhibitor; analgesic; anti-inflammatory.

9.10 Uses: Antibiotic

9.11 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.

9.12 Usage: 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.

9.13 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.

View all

9.14 Description: Ibuprofen is a white, crystalline anti-infl ammatory drug used in numerous medications. It is the active ingredient marketed under various trade names including Advil, Motrin, and Nurofen. Ibuprofen is a nonsteroidal anti-infl ammatory drug (NSAID) used as a pain reliever (analgesic), fever reducer (antipyretic), and inflammation reducer. Infl ammation is a general physiological response to tissue damage characterized by swelling, pain, and heat.
Ibuprofen works by inhibiting the enzyme cyclooxygenase (COX), which in turn interferes with the synthesis of prostaglandins. COX exists as several coenzyme forms that are similar in structure: COX-1, COX-2, COX-3; ibuprofen is a nonselective inhibitor of both COX-1 and COX-2. COX-1 is continually produced in mammalian cells throughout the body in response to physiological stimuli. It is responsible for the production of prostaglandins, which get their name because it was originally believed they were synthesized in the prostate gland. In fact, prostaglandins are synthesized throughout the body and act like hormones by stimulating action in target cells. Prostaglandins, which are fatty acid compounds consisting of a 20-carbon chain including a 5 carbon ring, are involved in numerous physiological processes including renal function, blood clotting, and stomach mucus production. COX-2 is synthesized only in specifi c parts of the body (kidneys, brain, trachea) as needed and is therefore called an induced enzyme. COX-2 produces prostaglandins in response to tissue damage and infl ammation. Infl ammatory prostaglandins produce swelling, pain, and fever.; View all

9.15 Originator: Brufen,Boots,UK,1969

9.16 History: Ibuprofen was developed while searching for an alternative pain reliever to aspirin in the 1950s. It 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. It 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.

9.17 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.; View all

9.18 Indications: Ibuprofen (Advil, Motrin) is used as an analgesic and antipyretic as well as a treatment for rheumatoid arthritis and degenerative joint disease. The most frequently observed side effects are nausea, heartburn, epigastric pain, rash, and dizziness. Incidence of GI side effects is lower than with indomethacin.Visual changes and cross-sensitivity to aspirin have been reported. Ibuprofen inhibits COX-1 and COX-2 about equally. It decreases platelet aggregation, but the duration is shorter and the effect quantitatively lower than with aspirin. Ibuprofen prolongs bleeding times toward high normal value and should be used with caution in patients who have coagulation deficits or are receiving anticoagulant therapy.

9.19 Manufacturing Process: Isobutylbenzene is first acetylated to give isobutylacetophenone. 4-ibutylacetophenone (40 g), sulfur (11 g) and morpholine (30 ml) were refluxed for 16 hours, cooled, acetic acid (170 ml) and concentrated hydrochloric acid (280 ml) were added and the mixture was refluxed for a further 7 hours. The mixture was concentrated in vacuo to remove acetic acid and the concentrate was diluted with water.
The oil which separated was isolated with ether, the ethereal solution was extracted with aqueous sodium carbonate and this extract was acidified with hydrochloric acid. The oil was isolated with ether, evaporated to dryness and the residue was esterified by refluxing with ethanol (100 ml) and concentrated sulfuric acid (3 ml) for 5 hours. The excess alcohol was distilled off, the residue was diluted with water, and the oil which separated was isolated with ether. The ethereal solution was washed with sodium carbonate solution; then with water and was dried. The ether was evaporated off and the oil was distilled to give ethyl 4-i-butylphenylacetate.
Sodium ethoxide from sodium (3.67 g) in absolute alcohol (64 ml) was added over 20 minutes with stirring to a mixture of ethyl 4-i-butylphenylacetate (28.14 g) and ethyl carbonate (102 ml) at 100°C. The reaction flask was fitted with a Fenske column through which alcohol and then ethyl carbonate distilled. After 1 hour when the still head reached 124°C heating was discontinued. Glacial acetic acid (12 ml) and water (50 ml) was added to the stirred ice-cooled mixture and the ester isolated in ether, washed with sodium carbonate solution, water and distilled to give ethyl 4-i-butylphenylmalonate.
Ethyl 4-i-butylphenylmalonate (27.53 g) in absolute alcohol (25 ml) was added with stirring to a solution of sodium ethoxide From sodium (2.17 g) in absolute alcohol (75 ml). Ethyl iodide (15 ml) was added and the mixture refluxed for 2% hours, the alcohol distilled and the residue diluted with water, extracted with ether, washed with sodium bisulfite, water, and evaporated to dryness.
The residual oil was stirred and refluxed with sodium hydroxide (75 ml of 5 N), water (45 ml) and 95% ethanol (120 ml). Within a few minutes a sodium salt separated and after 1 hour the solid was collected, washed with ethanol, dissolved in hot water and acidified with dilute hydrochloric acid to give the methyl malonic acid which was collected and dried in vacuo MP 177° to 180°C (dec.).
The malonic acid (9 g) was heated to 210° to 220°C in an oil bath for 20 minutes until decarboxylation had ceased. The propionic acid was cooled and recrystallized from light petroleum (BP 60° to 80°C). Two further recrystallizations from the same solvent gave colorless prisms of 2-(4- isobutylphenyl)propionicacid MP 75° to 77.5°C. (The procedure was reported in US Patent 3,228,831.); View all

9.20 Brand name: Abbifen;Abuprohm;Abu-tab;Aches-n-pain;Acril;Actifen;Actiprofen;Actren;Addaprin;Advil 200 mg;Advil cold & sinus;Agisan;Aktren;Aldospray;Algiasdin;Algifor;Algisan;Algofer;Altior;Amersol;Anadin ibuprofen;Analgesico;Analgil;Analgyl;Anco;Antalgil;Antiflam;Antiruggen;Apsifen;Artofen;Artren;Artril;Artrofen;Bayer select ibuprofen pain reliever;Benflogin;Betagesic;Betaprofen;Brofen 200 mg;Brofen 400 mg;Brufert;Brufort;Buborone;Bufedon;Bufigen;Burana;Cesra;Children's advil;Children's motrin;Codafen continus;Contraneural;Contrneural;Cuisialigil;Cunil;Cuprofen;Dansida;Dentigoa forte;Dignoflex;Dimetap sinus;Dimidon;Dismenodl n;Dolgirit;Dolocyl;Dolo-dolgit;Dologesic;Dolo-neos;Dolo-puren;Doltibil;Dolven;Donjust-b;Dorival;Dristan sinus;Duradyne;Dura-ibu;Duralbuprofen;Dysdolen;Ecoprofen;Ediluna;Esprenit;Excedrin ib;Exidol;Exneural;Femafen;Femapirin;Femidol;Fenalgic;Fenlong;Genpril;Guildprofen;Halprin;Ibenon;Ibol;Ibosure;Ibruthalal;Ibu-attritin;Ibucasen;Ibu-cream;Ibufac;Ibufen tablets;Ibufen-l;Ibufug;Ibugel;Ibugesic;Ibuhexal;Ibular;Ibulav;Ibuleve;Ibulgan;Ibumetin;Ibuphlogont;Ibupirac;Ibuprin;Ibuprofen 200;Ibuprohm;Ibu-slow;Ibusure;Ibu-tab;Ibutad;Ibutid;Ibutop;Ibuvivimed;Ibux;Imben;Inabrin;Incefal;Inflam;Inoven;Inza;Iproben;Irfen;Isdol;Isisfen;Junifen;Kalma;Kos;Lacondan;Librofem;Librofen;Lidifen;Lisi-budol;Mediprofen;Melfen;Menado ibuprofen usp;Midol 200 advanced pain formula;Midol ib;Migrafen;Minadol;Moment;Motrin ib;Narfen;Neobrofen;Neobrufen;Nerofen;Niapren;Novaprin;Novogent;Novoprofen;Nu-ibuprofen;Optifen;Opturem;Pacifene;Padudent;Paxofen;Pfeil;Phor pain;Posodolor;Prontalgin;Recudik;Relcofen;Rheufen;Rimafen;Saleto-600;Seclodin;Sedaspray;Serviprofen;Sine-aid ib;Solufen;Spedifen;Stadasan;Superior pain medicine;Supreme pain medicine;Supren;Suspren;Tabalon;Tempil;Tendar;Trauma-dolgit;Ultraprin;Valprin.; View all

9.21 Therapeutic Function: Antiinflammatory

9.22 World Health Organization (WHO): Ibuprofen, a non-steroidal anti-inflammatory agent, was introduced in 1969. It was approved for sale without prescription in packages containing no more than 400 mg, in the United Kingdom in 1983. This action was followed by the USA, Canada and several European countries. Since this time reports of suspected adverse effects have increased. Most of these relate to gastrointestinal disturbances, hypersensitivity reactions but aseptic meningitis, skin rashes and renal damage have been recorded.

9.23 Synthesis Reference(s): Chemical and Pharmaceutical Bulletin, 31, p. 3139, 1983 DOI: 10.1248/cpb.31.3139
The Journal of Organic Chemistry, 52, p. 287, 1987 DOI: 10.1021/jo00378a027

9.24 General Description: Ibuprofen, 2-(4-isobutylphenyl)propionic acid (Motrin,Advil, Nuprin), was introduced into clinical practice followingextensive clinical trials. It appears to have comparableefficacy to aspirin in the treatment of RA, but with a lowerincidence of side effects. It 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.

9.25 Biochem/physiol Actions: Primary TargetCOX-1

9.26 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.

9.27 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.

9.28 Chemical Synthesis: Ibuprofen, 2-(4-iso-butylphenyl)propionic acid (3.2.23), can be synthesized by various methods [88–98]. The simplest way to synthesize ibuprofen is by the acylation of iso-butylbenzol by acetyl chloride. The resulting iso-butylbenzophenone (3.2.21) is reacted with sodium cyanide, giving oxynitrile (3.2.22), which upon reaction with hydroiodic acid in the presence of phosphorus is converted into 2-(4-iso-butylphenyl)propionic acid (3.2.23), which subsequently undergoes phases of dehydration, reduction, and hydrolysis.

Another way to synthesize ibuprofen consists of the chloromethylation of iso-butylbenzene, giving 4-iso-butylbenzylchloride (3.2.24). This product is reacted with sodium cyanide, making 4-iso-butylbenzyl cyanide (3.2.25), which is alkylated in the presence of sodium amide by methyl iodide into 2-(4-iso-butylbenzyl)propionitrile (3.2.26). Hydrolysis of the resulting product in the presence of a base produces ibuprofen (3.2.23).; View all

9.29 Environmental Fate: Ibuprofen has a high water solubility and low volatility, which suggest a high mobility in the aquatic environment. This makes it a commonly detected chemical of the pharmaceutical and personal care products (PPCPs) in the environment. It is not as persistent, however, as many other chemicals. Ibuprofen undergoes photodegradation with exposure to direct and indirect sunlight, although degradation products can have effects on aquatic environments.

9.30 Metabolism: Metabolism occurs rapidly, and the drug is nearly completely excreted in the urine as unchanged drug and oxidative metabolites within 24 hours following administration. Metabolism by CYP2C9 (90%) and CYP2C19 (10%) involves primarily ω-, and ω1-, and ω2-oxidation of the p-isobutyl side chain, followed by alcohol oxidation of the primary alcohol resulting from ω–oxidation to the corresponding carboxylic acid. All metabolites are inactive. When ibuprofen is administered as the individual enantiomers, the major metabolite isolated is the S-(+)-enantiomer whatever the configuration of the starting enantiomer. Interestingly, the R-(–)-enantiomer is inverted to the S-(+)-enantiomer in vivo via an acetyl–coenzyme A intermediate, accounting for the observation that the two enantiomers are bioequivalent in vivo. This is a metabolic phenomenon that also has been observed for other arylpropionic acids, such as ketoprofen, benoxaprofen, fenoprofen, and naproxen.

9.31 Toxicity evaluation: The mechanisms of ibuprofen-induced toxicity have not been clearly defined. Acute renal failure is postulated to result from decreased production of intrarenal prostaglandins via inhibition of the cyclooxygenase pathway. In turn, this will decrease the renal blood flow and glomerular filtration rate. Ibuprofen also interferes with prostaglandin synthesis in the gastrointestinal system, which can contribute to its irritating effect on the mucosa of the gastrointestinal tract. Anion gap metabolic acidosis is likely caused by elevated lactate due to hypotension and hypoperfusion and also due to ibuprofen and its metabolites, which are all weak acids. Seizures have been reported in large ibuprofen overdoses, but the mechanism of toxicity remains unknown. In massive overdoses, ibuprofen is thought to have cellular toxicity disrupting mitochondrial energy processes causing the formation of lactic acid.

10. Computational chemical data

Molecular Weight: 206.28082g/mol
Molecular Formula: C₁₃H₁₈O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 206.130679813
Monoisotopic Mass: 206.130679813
Complexity: 203
Rotatable Bond Count: 4
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 37.3
Heavy Atom Count: 15
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceBwMAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgAACAAADQCAmAAyCIAAAgCIAiDSCAACAAAgAAAIiAEAAIgIIDKAFRCAYAAkwAEIiAeIyOCOwAAAAAAAAACAAAAAAAAAAAAAAAAAAA==

11. Question & Answer

How is Ibuprofen Synthesized and What Recent Advances Have Been Made? Jul 29 2024
Inflammation is a natural defense response of the immune system to non-self-recognition or unusual self-abnormality. While this process protects our body from disorders, it can also cause unwanted phy..
Can Ibuprofen and Excedrin be Taken Together? Mar 09 2024
Ibuprofen Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) that reduces inflammation and pain in the body. It is commonly used to reduce fever and treat pain or inflammation from various con..
What are the uses, side effects, and risks of Ibuprofen? Mar 09 2024
Uses Ibuprofen, a non-steroidal anti-inflammatory drug (NSAID), is utilized for various conditions, including: Inflammation Mild to moderate pain Severe pain (when combined with codeine) Fever Rheumat..
What is the mechanism of action of ibuprofen and how is it used in treating various conditions? Nov 14 2023
Description Ibuprofen is an organic compound with the chemical formula C13H18O2, also known as 2-(4-Isobutylphenyl)propionic Acid. It is a white to off-white powder that is practically insoluble in wa..

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