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| | ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID Basic information |
| | 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) |
| 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) |
| | 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 | analgesic, antiinflammatory | | Uses | ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID is a non-steroidal anti-inflammatory agent used for treatment of pain and inflammation | | 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 Initially used as an anti-inflammatory and analgesic, it was withdrawn from the market due to causi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 ACID Preparation Products And Raw materials |
| Raw materials | Ethyl 2-chloromethylbenzoate-->Potassium hydroxide-->Benzeneacetic acid, 4-(1,3-dihydro-1-oxo-2H-isoindol-2-yl)-α-methyl-, ethyl ester-->Benzeneacetic acid, 4-(1,3-dihydro-1-oxo-2H-isoindol-2-yl)-α-methyl-, methyl ester-->Benzeneacetic acid, 4-(1,3-dihydro-2H-isoindol-2-yl)-α-methyl-, ethyl ester-->1H-Isoindol-1-one, 2-(4-chlorophenyl)-2,3-dihydro--->4-aminohydratropic acid-->ethyl 2-(4-aminophenyl)propionate-->2-(4-NITROPHENYL)PROPIONIC ACID-->ethyl 2-(4-nitrophenyl)propionate-->ZINC-->carbon monoxide-->Carbon dioxide-->2-Carboxybenzaldehyde |
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