Ibuprofen

Base Information

• Chemical Name: Ibuprofen
• CAS No.: 15687-27-1
• Deprecated CAS: 58560-75-1,139466-08-3
• Molecular Formula: C13H18O2
• Molecular Weight: 206.285
• Hs Code.: 2916.39
• European Community (EC) Number: 239-784-6
• NSC Number: 757073,256857
• UNII: WK2XYI10QM
• DSSTox Substance ID: DTXSID5020732
• Nikkaji Number: J3.134H
• Wikipedia: Ibuprofen
• Wikidata: Q186969
• NCI Thesaurus Code: C561
• RXCUI: 5640
• Pharos Ligand ID: JSNCQPWTHATF
• Metabolomics Workbench ID: 141986
• ChEMBL ID: CHEMBL521
• Mol file: 15687-27-1.mol

Synonyms:Advil;alpha-Methyl-4-(2-methylpropyl)benzeneacetic Acid;Benzeneacetic Acid, alpha-methyl-4-(2-methylpropyl)- trimethylsilyl ester;Brufen;Ibumetin;Ibuprofen;Ibuprofen Zinc;Ibuprofen, (+-)-Isomer;Ibuprofen, (R)-Isomer;Ibuprofen, (S)-Isomer;Ibuprofen, Aluminum Salt;Ibuprofen, Calcium Salt;Ibuprofen, Copper (2+) Salt;Ibuprofen, Magnesium Salt;Ibuprofen, Potassium Salt;Ibuprofen, Sodium Salt;Ibuprofen, Zinc Salt;Ibuprofen-Zinc;Motrin;Nuprin;Rufen;Salprofen;Trauma Dolgit Gel;Trauma-Dolgit Gel

Chemical Property of Ibuprofen

Chemical Property:

• Appearance/Colour: Colourless, crystalline solid
• Vapor Pressure: 0.000139mmHg at 25°C
• Melting Point: 77-78 °C(lit.)
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 319.6 °C at 760 mmHg
• PKA: pKa 4.45± 0.04(H2O,t = 25±0.5,I=0.15(KCl))(Approximate)
• Flash Point: 216.7 °C
• PSA: 37.30000
• Density: 1.029 g/cm³
• LogP: 3.07320
• Storage Temp.: -20?C Freezer
• Solubility.: Practically insoluble in water, freely soluble in acetone, in methanol and in methylene chloride. It dissolves in dilute solutions of alkali hydroxides and carbonates.
• Water Solubility.: insoluble
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 206.130679813
• Heavy Atom Count: 15
• Complexity: 203

Purity/Quality:

99.8% ^*data from raw suppliers

racIbuprofen ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N,T,F
• Statements: 22-63-51/53-39/23/24/25-23/24/25-11
• Safety Statements: 36-61-36/37-45-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Nonsteroidal Antiinflammatory Drugs
• Canonical SMILES: CC(C)CC1=CC=C(C=C1)C(C)C(=O)O
• Recent ClinicalTrials: Pain Management Following Sinus Surgery
• Recent EU Clinical Trials: A Phase III Prospective, Randomized, Multicenter, Double-Blind, Placebo-controlled clinical study to evaluate the efficacy and safety of fixed dose combination (FDC) product Ibuprofen/Paracetamol/Phenylephrine Hydrochloride 200 mg/500 mg/10 mg film-coated tablets (containing Ibuprofen 200 mg, Paracetamol 500 mg and Phenylephrine Hydrochloride 10 mg) compared to Doregrippin? 500 mg/10 mg film-coated tablets (containing Paracetamol 500 mg and Phenylephrine Hydrochloride 10 mg) and Nurofen? 200 mg Tablets (containing Ibuprofen 200 mg) for the temporary relief of cold and flu symptoms, i.e. mild to moderate pain, sore throat, fever and nasal congestion.
• Recent NIPH Clinical Trials: The effect of intravenous ibuprofen on postoperative pain and opioid consumption after pediatric cardiac surgery
• Chemical Structure and Properties: Ibuprofen is a monocarboxylic acid derived from propionic acid, with one of the hydrogens substituted by a 4-(2-methylpropyl)phenyl group.; It is a colorless, crystalline solid with a characteristic odor. Ibuprofen is a non-steroidal anti-inflammatory drug (NSAID) used for the treatment of fever, muscle pain, and inflammation.; Its discovery dates back to 1961 by Stewart Adams, and it remains one of the most prescribed NSAIDs today.
• History and Market Presence: Initially introduced for prescription use in the UK in 1969 (as Brufen) and in the US in 1974, ibuprofen later transitioned to over-the-counter (OTC) sales in both countries in the 1980s. It gained popularity for various pain complaints, including headaches.
• Usage and Consumption: Ibuprofen is rapidly absorbed by the body but has a short half-life, requiring frequent dosing. It belongs to the group of NSAIDs and is the third most consumed drug worldwide, with a significant annual output. ; Ibuprofen is listed as a priority substance by regulatory bodies due to its environmental impact.
• Pharmacokinetics and Metabolism: The therapeutic doses of ibuprofen range from 600 to 1200mg/day. After oral administration, ibuprofen primarily binds to plasma albumin and undergoes metabolism to several metabolites, which are eventually excreted.
• Formulation and Delivery: Traditional formulations of ibuprofen have poor water solubility, necessitating higher doses for therapeutic effect.; The development of a water-soluble form of ibuprofen is essential, especially for targeting high concentrations in the lungs using inhalation devices.
• Therapeutic Potential Beyond Pain Relief: In silico predictions suggest ibuprofen's potential as an entry inhibitor for viruses like Ebola and Zika, with experimental confirmations of its virucidal effects. Ibuprofen has also shown promise in the treatment of patent ductus arteriosus (PDA) in preterm infants by inhibiting cyclooxygenase.

Technology Process of Ibuprofen

There total 213 articles about Ibuprofen which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

ibuproxam (53648-05-8) → 1-(4-isobutyl-phenyl)-ethanone (38861-78-8) + ibuprofen (15687-27-1,58560-75-1) + 4'-(2-methylpropyl)acetophenone oxime (74305-51-4) + 4-(2-methylpropyl)phenylethylamine (164579-51-5)

Guidance literature:

at 110 ℃; for 24h; under 760 Torr; Product distribution; other temperature, reaction time;

DOI:10.1002/jps.2600690511

Reference yield: 87.0%

→ ibuprofen (15687-27-1,58560-75-1) + (+/-)-ibuprofen methyl ester (61566-34-5)

Guidance literature:

Reference yield: 83.0%

→ ibuprofen (15687-27-1,58560-75-1) + (S)-ibuprofen (51146-56-6,58560-75-1)

Guidance literature:

upstream raw materials:

4-Butyl-α-methyl-β-dichlorostyren

1-Isobutyl-4-(1-methyl-2,2-bis-methylsulfanyl-vinyl)-benzene

trichlorofluoromethane

1-(4-isobutyl-phenyl)-ethanone

Downstream raw materials:

(+/-)-ibuprofen methyl ester

2-(4-isobutylphenyl)propionic acid N-oxysuccinimide ester

4-Nitrophenyl 2-(4-isobutylphenyl)propanoate

C₁₆H₂₂O₄

Refernces

• 1、 Khan,Akhter, Mymoona. "Synthesis, pharmacological activity and hydrolytic behavior of glyceride prodrugs of ibuprofen". . p. 371 - 376. Retrieved 2005.
• 2、 Nugent, William A.,McKinney, Ronald J.. "Nickel-Catalyzed Markovnikov Addition of Hydrogen Cyanide to Olefins. Application to Nonsteroidal Antiinflammatories". . p. 5370 - 5372. Retrieved 1985.
• 3、 Walker,Pillai. "-". . p. 3707. Retrieved 1977.
• 4、 Jayasree,Seayad,Chaudhari. "Highly active supported palladium catalyst for the regioselective synthesis of 2-arylpropionic acids by carbonylation". . p. 1067 - 1068. Retrieved 1999.
• 5、 Tamura, Yasumitsu,Shirouchi, Yoshiaki,Haruta, Jun-ichi. "Synthesis of Methyl 2-Arylpropanoates by 1,2-Aryl Migration of Aryl Ethyl Ketones using Diacetoxyphenyliodine". . p. 231 - 232. Retrieved 1984.
• 6、 Seayad,Jayasree,Chaudhari. "Carbonylation of vinyl aromatics: Convenient regioselective synthesis of 2-arylpropanoic acids". . p. 459 - 461. Retrieved 1999.
• 7、 Chimichi,Innocenti,Orzalesi. "Thermal decomposition of ibuproxam". . p. 521 - 523. Retrieved 1980.
• 8、 Shiori,Kawai. "-". . p. 2936. Retrieved 1978.
• 9、 Reetz, Manfred T.,Carballeira, Jose Daniel,Peyralans, Jerome,Hoebenreich, Horst,Maichele, Andrea,Vogel, Andreas. "Expanding the substrate scope of enzymes: Combining mutations obtained by CASTing". . p. 6031 - 6038. Retrieved 2006.
• 10、 An, Yi,Chen, Fener,Li, Weijian,Li, Yaling,Tang, Pei,Wang, Zhenzhen,Wu, Mengjuan,Xue, Yansong. "The total synthesis of (-) -strempeliopine: Via palladium-catalyzed decarboxylative asymmetric allylic alkylation". . p. 1402 - 1405. Retrieved 2022/02/09.