ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID
ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID Basic information
- Product Name:
- ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID
- Synonyms:
-
- ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID
- 1-oxo-2-(p-((alpha-methyl)carboxymethyl)phenyl)isoindoline
- 2-(4-(1-carboxyethyl)phenyl)-1-isoindolinone
- 2-(p-(1-oxo-2-isoindolinyl)phenyl)-propionicaci
- 4-(1,3-dihydro-1-oxo-2h-isoindol-2-yl)-alpha-methyl-benzeneaceticaci
- 4-(1,3-dihydro-1-oxo-2h-isoindol-2-yl)-alpha-methylbenzeneaceticacid
- alpha-(4-(1-oxo-2-isoindolinyl)phenyl)-propionicaci
- alpha-(4-(1-oxo-2-iso-indolinyl)-phenyl)-propionicacid
- CAS:
- 31842-01-0
- MF:
- C17H15NO3
- MW:
- 281.31
- EINECS:
- 250-833-0
- Product Categories:
-
- Pharmaceuticals
- Aromatics
- Heterocycles
- Intermediates & Fine Chemicals
- Mol File:
- 31842-01-0.mol
ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID Chemical Properties
- Melting point:
- 213-214°
- Boiling point:
- 423.97°C (rough estimate)
- Density
- 1.1302 (rough estimate)
- refractive index
- 1.4500 (estimate)
- storage temp.
- 2-8°C
- solubility
- Methanol (Slightly, Sonicated)
- pka
- pKa 5.8 (Uncertain)
Safety Information
- Hazard Codes
- T
- Risk Statements
- 25-40
- Safety Statements
- 22-36/37/39-45
- RIDADR
- UN 2811 6.1 / PGIII
- WGK Germany
- 3
- RTECS
- MU6645000
- Toxicity
- LD50 in rats (mg/kg): 58.66 i.v.; 60.83 orally (Buttinoni)
MSDS
- Language:English Provider:SigmaAldrich
ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID Usage And Synthesis
Chemical Properties
ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID is Off-White Solid
Originator
Flosint,Carlo Erba,Italy,1976
Uses
ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID is a non-steroidal anti-inflammatory agent used for treatment of pain and inflammation
Uses
analgesic, antiinflammatory
Definition
ChEBI: A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-(1-oxo-1,3-dihydroisoindol-2-yl)phenyl group. Initially used as an anti-inflammatory and analgesic, it was withdrawn from the market due to causi g severe gastrointestinal bleeding. It has been subsequently found to increase production of the survival motor neuron protein.
Manufacturing Process
The mixture of 7.9 g of ethyl α-(4-aminophenyl)propionate and 8.3 g of ethyl 2-chloromethylbenzoate is refluxed under nitrogen for one hour. The residue is recrystallized from hexane, to yield the ethyl α-[4-(1-oxo-isoindolino)-phenyl]- propionate of the formulamelting at 104° to 106°C. The mixture of 4.5 g thereof, 1.6 g of potassiumhydroxide, 2 ml of water and 250 ml of ethanol is refluxed under nitrogen for 2 hours and evaporated under reduced pressure. The residue is taken up in water, the solution washed with chloroform, acidified with hydrochloric acid and extracted with ethyl acetate. The extract is dried, evaporated and the residue recrystallized from ethyl acetate, to yield the corresponding free acid melting at 208° to 210°C. (Procedure reported in US Patent 3,767,805.)
brand name
Endyne;Fenint;Flogosan;Flosine;Flosyn;K 4277;Miantor.
Therapeutic Function
Antiinflammatory
World Health Organization (WHO)
Indoprofen, a nonsteroidal anti-inflammatory agent, was introduced in 1976 for the treatment of rheumatic disorders. By 1983 its use had been associated with serious adverse effects, some of which were fatal. This led to its withdrawal in the United Kingdom and Cyprus. In 1984 reports of intestinal tumours in rats led to the drug's temporary withdrawal in Germany and Italy. This was followed immediately by the suspension of marketing worldwide by the major manufacturer.
ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACIDSupplier
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ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID(31842-01-0)Related Product Information
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