83394-44-9

Basic information

• Product Name: Aminoprofen
• Synonyms: Aminoprofen;Benzeneacetamide, N-(2-hydroxyethyl)-alpha-methyl-4-(2-methylpropyl)-;N-(2-Hydroxyethyl)-alpha-methyl-4-(2-methylpropyl)benzeneacetamide;N-(beta-Hydroxyethyl)-DL-2-(4'-isobutylphenyl)propionamide
• CAS NO: 83394-44-9
• Molecular Formula: C15H23NO2
• Molecular Weight: 249.352
• Mol File: 83394-44-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 445.5°Cat760mmHg
• Flash Point: 223.2°C
• Appearance: /
• Density: 1.029g/cm³
• CAS DataBase Reference: Aminoprofen(CAS DataBase Reference)
• NIST Chemistry Reference: Aminoprofen(83394-44-9)
• EPA Substance Registry System: Aminoprofen(83394-44-9)

Safety Data

• Hazardous Substances Data: 83394-44-9(Hazardous Substances Data)

Usage

Description

Aminoprofen, an amide of ibuprofen, is a topical anti-arthritic with analgesic properties. It is comparable to methyl salicylate in the carrageenan-induced paw edema and croton oil ear edema models, and is reported to be a superior analgesic.

Upstream product

• 71381-91-4 (+/-)-2-(4-isobutylphenyl)propanoyl chloride 
• 141-43-5 ethanolamine 
• 41283-72-1 ibuprofen ethyl ester 
• 15687-27-1 ibuprofen 
• 51146-57-7 (R)-ibuprofene 
• 114978-05-1 (R)-2-(4-isobutylphenyl)propionyl chloride 

Relevant articles and documents

Synthesis, characterization, and biological evaluation of furoxan coupled ibuprofen derivatives as anti-inflammatory agents

A series of furoxan-based nitric oxide releasing ibuprofen derivatives were synthesized and tested for their anti-inflammatory, analgesic, ulcerogenic, lipid peroxidation, and hepatotoxic properties. The compounds exhibited more protection than ibuprofen with regard to gastric toxicity. Among the tested compounds 4-[2-[2-(4-isobutylphenyl)propanamido]ethoxycarbonyl]-3-methylfuroxan and 4-[2-[2-(4-isobutylphenyl)propanoyl]hydrazinecarbonyl]-3-phenylfuroxan emerged as most active anti-inflammatory agents with reduced gastrotoxicity. The results showed that incorporation of NO donating group caused a moderate increase in anti-inflammatory activity with a marked decrease in gastric ulcerations compared to their parent drug ibuprofen. A molecular docking study of all the compounds was also performed to provide the binding modes of COX-1 enzyme. Among all the titled compounds, 4-[2-[2-(4-isobutylphenyl)propanamido]ethoxycarbonyl]-3-methylfuroxan was found to be most potent and have high docking score showing favorable orientation within the COX-1 binding site.

2-Arylpropionic CXC chemokine receptor 1 (CXCR1) ligands as novel noncompetitive CXCL8 inhibitors

The CXC chemokine CXCL8/IL-8 plays a major role in the activation and recruitment of polymorphonuclear (PMN) cells at inflammatory sites. CXCL8 activates PMNs by binding the seven-transmembrane (7-TM) G-protein-coupled receptors CXC chemokine receptor 1 (CXCR1) and CXC chemokine receptor 2 (CXCR2). (R)-Ketoprofen (1) was previously reported to be a potent and specific noncompetitive inhibitor of CXCLS-induced human PMNs chemotaxis. We report here molecular modeling studies showing a putative interaction site of 1 in the TM region of CXCR1. The binding model was confirmed by alanine scanning mutagenesis and photoaffinity labeling experiments. The molecular model driven medicinal chemistry optimization of 1 led to a new class of potent and specific inhibitors of CXCL8 biological activity. Among these, repertaxin (13) was selected as a clinical candidate drug for prevention of post-ischemia reperfusion injury.