158836-71-6

Basic information

• Product Name: nitroflurbiprofen
• Synonyms: nitroflurbiprofen
• CAS NO: 158836-71-6
• Molecular Formula: C19H20FNO5
• Molecular Weight: 361.367
• Mol File: 158836-71-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 468.8°Cat760mmHg
• Flash Point: 237.3°C
• Appearance: /
• Density: 1.214g/cm³
• Vapor Pressure: 5.79E-09mmHg at 25°C
• Refractive Index: 1.537
• CAS DataBase Reference: nitroflurbiprofen(CAS DataBase Reference)
• NIST Chemistry Reference: nitroflurbiprofen(158836-71-6)
• EPA Substance Registry System: nitroflurbiprofen(158836-71-6)

Safety Data

• Hazardous Substances Data: 158836-71-6(Hazardous Substances Data)

Usage

Definition

ChEBI: A carboxylic ester obtained by formal condensation of the carboxy group of flurbiprofen with the free hydroxy group of 4-(nitrooxy)butanol. It is a non-steroidal anti-inflammatory agent showing inhibitory effects against the cyclooxygenases COX1 and COX2.

InChI:InChI=1/C19H20FNO5/c1-14(19(22)25-11-5-6-12-26-21(23)24)16-9-10-17(18(20)13-16)15-7-3-2-4-8-15/h2-4,7-10,13-14H,5-6,11-12H2,1H3

Upstream product

• 5104-49-4 fluorobiprofen 
• 156970-84-2 4-bromobutyl 2-fluoro-α-methyl-4-diphenylacetate 

Relevant articles and documents

Inhibition of amyloidogenesis by nonsteroidal anti-inflammatory drugs and their hybrid nitrates

Poor blood-brain barrier penetration of nonsteroidal anti-inflammatory drugs (NSAIDs) has been blamed for the failure of the selective amyloid lowering agent (SALA) R-flurbiprofen in phase 3 clinical trials for Alzheimer's disease (AD). NO-donor NSAIDs (NO-NSAIDs) provide an alternative, gastric-sparing approach to NSAID SALAs, which may improve bioavailability. NSAID analogues were studied for anti-inflammatory activity and for SALA activity in N2a neuronal cells transfected with human amyloid precursor protein (APP). Flurbiprofen (1) analogues were obtained with enhanced anti-inflammatory and antiamyloidogenic properties compared to 1, however, esterification led to elevated A 1-42 levels. Hybrid nitrate prodrugs possessed superior anti-inflammatory activity and reduced toxicity relative to the parent NSAIDs, including clinical candidate CHF5074. Although hybrid nitrates elevated A 1-42 at higher concentration, SALA activity was observed at low concentrations (1 μM): both A1-42 and the ratio of A 42/A1-40 were lowered. This biphasic SALA activity was attributed to the intact nitrate drug. For several compounds, the selective modulation of amyloidogenesis was tested using an immunoprecipitation MALDI-TOF approach. These data support the development of NO-NSAIDs as an alternative approach toward a clinically useful SALA.