1553-60-2

Basic information

• Product Name: IBUFENAC
• Synonyms: (p-isobutylphenyl)-aceticaci;(p-isobutylphenyl)aceticacid;4-(2-methylpropyl)-benzeneaceticaci;4-(2-methylpropyl)benzeneaceticacid;dytransin;ibufenac;ibunac;isodilan
• CAS NO: 1553-60-2
• Molecular Formula: C₁₂H₁₆O₂
• Molecular Weight: 192.25424
• EINECS: 216-302-2
• Product Categories: Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 1553-60-2.mol

Chemical Properties

• Melting Point: 85-87°C
• Boiling Point: 288.25°C (rough estimate)
• Flash Point: 209.3°C
• Appearance: /
• Density: 1.0240 (rough estimate)
• Vapor Pressure: 0.000229mmHg at 25°C
• Refractive Index: 1.5100 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.36±0.10(Predicted)
• CAS DataBase Reference: IBUFENAC(CAS DataBase Reference)
• NIST Chemistry Reference: IBUFENAC(1553-60-2)
• EPA Substance Registry System: IBUFENAC(1553-60-2)

Safety Data

• Hazardous Substances Data: 1553-60-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
IBUFENAC is used as an analgesic and anti-inflammatory agent for the relief of pain and reduction of inflammation in various conditions, such as rheumatoid arthritis. Its effectiveness in these applications was demonstrated before its clinical use was discontinued due to hepatotoxic side effects.
Used in Research and Development:
IBUFENAC may still be utilized in research and development for the study of its chemical properties, potential modifications, and the development of safer alternatives with similar analgesic and anti-inflammatory effects.

Biological Activity

ibufenac is a dual cox-1 and -2 inhibitor.cyclooxygenase (cox), also known as prostaglandin-endoperoxide synthase (ptgs), is an enzyme that is responsible for formation of prostanoids, such as thromboxane and prostaglandins.

in vitro

ibufenac was identified as an analog of the nsaid ibuprofen that could inhibit cox-1 and -2 activity with ic50 values of 17.4 and 13.1 μm, respectively [1].

in vivo

in a previous animal study, two new structural analogs, r3 and r4, along with their parent compounds, ibufenac and ibuprofen, were evaluated for their biopharmaceutical properties. aanti-inflammatory activity was evaluated by topically administering drugs to inhibit inflammation induced by using either clove oil or arachidonic acid. results showed that the rank order of activity was ibufenac approximately equal to ibuprofen > r3 approximately equal to r4 [2].

IC 50

17.4 and 13.1 μm for cox-1 and -2, respectively.

references

[1] gülcan, h. o.,nlü, s.,dimoglo, a., et al. marginally designed new profen analogues have the potential to inhibit cyclooxygenase enzymes. arch.pharm.chem.life sci. 348, 55-61 (2015).[2] rao cs, schoenwald rd, barfknecht cf, laban sl. biopharmaceutical evaluation of ibufenac, ibuprofen, and their hydroxyethoxy analogs in the rabbit eye. j pharmacokinet biopharm. 1992 aug;20(4):357-88.[3] t. m. chalmers.

InChI:InChI=1/C12H16O2/c1-9(2)7-10-3-5-11(6-4-10)8-12(13)14/h3-6,9H,7-8H2,1-2H3,(H,13,14)/p-1

Upstream product

• 124-38-9 carbon dioxide 
• 5161-04-6 1-methyl-4-(2-methylpropyl)-benzene 
• 38861-78-8 1-(4-isobutyl-phenyl)-ethanone 
• 60736-79-0 1-(Chloromethyl)-4-isobutylbenzene 
• 15649-02-2 ethyl p-isobutylphenyl acetate 
• 58142-20-4 (4-isobutyl-2-oxo-3-cyclohexen-1-yl)acetic acid 
• 110-91-8 morpholine 
• 142521-09-3 1-(2,2-dibromovinyl)-4-isobutylbenzene 
• 15687-27-1 ibuprofen 
• 99-90-1 para-bromoacetophenone 
• 36039-35-7 R-(+)-2-(4-isobutylphenyl)-hydroxy-ethane 
• 4654-39-1 4-bromophenethanol 
• 4360-68-3 2-(4-bromophenyl)-2-methyl-1,3-dioxolane 
• 40150-98-9 4-(2-methyl-1-propyl)benzaldehyde 

Downstream Products

• 75581-00-9 4-(2-methylpropyl)-β,β-bis(trimethylsiloxy)styrene 
• 38588-43-1 p-isobutylphenylacetic acid chloride 
• 15687-27-1 ibuprofen 
• 915315-36-5 (4R,5S)-N-(4-isobutylphenyl acetyl)-4-methyl-5-phenyl-2-oxazolidinone 
• 40784-94-9 p-Isobutylphenylacetamid 
• 71381-91-4 (+/-)-2-(4-isobutylphenyl)propanoyl chloride 

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