ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID is Off-White Solid
Flosint,Carlo Erba,Italy,1976
analgesic, antiinflammatory
ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID is a non-steroidal anti-inflammatory agent used for treatment of pain and inflammation
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 Initially used as an anti-inflammatory and analgesic, it was withdrawn from the market due to causi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.
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.)
Endyne;Fenint;Flogosan;Flosine;Flosyn;K 4277;Miantor.
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.