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

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)

Upstream product

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

NSAIDs do not require the presence of a carboxylic acid to exert their anti-inflammatory effect – why do we keep using it?

The carboxylic acid group (–COOH) present in classical NSAIDs is partly responsible for the gastric toxicity associated with the administration of these drugs. This concept has been extensively proven using NSAID prodrugs. However, the screening of NSAIDs

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.