Fendosal Chemical Properties

Melting point:

223-225° (dec)

Boiling point:

508.82°C (rough estimate)

Density 

1.2182 (rough estimate)

refractive index 

1.6000 (estimate)

pka

2.40±0.10(Predicted)

CAS DataBase Reference

53597-27-6(CAS DataBase Reference)

Safety Information

Toxicity

LD50 in mice, rats, rabbits (mg/kg): 740, 450, 560 orally; in mice (mg/kg): 510 i.p. (Lassman)

Fendosal Usage And Synthesis

Originator

Alnovin,Hoechst

Uses

Anti-inflammatory.

Definition

ChEBI: Fendosal is a benzoindole that is 4,5-dihydro-3H-benzo[e]indole in which the nitrogen is substituted by a 3-carboxy-4-hydroxyphenyl group. A non-narcotic analgesic and non-steroidal anti-inflammatory drug, it has greater analgesic and inflammatory responses than aspirin but with less gastrointestinal toxicity. It has a role as a non-steroidal anti-inflammatory drug and a non-narcotic analgesic. It is a member of pyrroles, a benzoindole and a monohydroxybenzoic acid.

Manufacturing Process

To a stirred refluxing solution of 20.2 g (0.1 mole) of 1-(1-pyrrolidino)-3,4- dihydronaphthalene and 50 ml of toluene was added dropwise during 30 minutes under nitrogen a solution of 20.1 g (0.1 mole) of phenacyl bromide in 65 ml of dry toluene. The mixture was heated under reflux for 6 hours, diluted with 50 ml of water, refluxed for 4 hours, and cooled. The layers were separated and the aqueous phase was extracted with benzene. The organic solution was dried over sodium sulfate and concentrated to a semi-solid. Trituration with cold 30°-60° petroleum ether gave 23.6 g (78%) of solid, 2- phenacyl-1-tetralone, MP: 73°-76°C. Recrystallization from 60°-90° petroleum ether raised the melting point to 87°-88°C.
A mixture of 20.0 g (0.076 mole) of 2-phenacyl-1-tetralone, 11.6 g (0.076 mole) of 5-aminosalicyclic acid, and 70 ml of glacial acetic acid was heated under reflux for 4 hours, cooled, diluted with 10 ml of water and filtered. The filter cake was washed with water and dried to provide 15.5 g of solid, 5-(4,5- dihydro-2-phenyl-3H-benz[e]indol-3-yl)-2-hydroxy-benzoic acid. MP: 215°- 218°C. Recristallization from benzene-cyclohexane gave 6.5 g (22%) of yellow crystals, MP: 245°-247°C.

brand name

Alnovin(Hoechst-Roussel).

Therapeutic Function

Analgesic, Antiinflammatory, Antipyretic

Fendosal(53597-27-6)Related Product Information

• PHENYL VALERATE
• Indometacin
• Salicylic acid
• cis-Octahydroisoindole
• Indole-3-butyric acid
• Indole-3-acetic acid
• Dihydromyrcenol
• Domiphen bromide
• Phenylacetic acid
• 3-(1H-PYRROL-1-YL)BENZOIC ACID
• 3-(1H-PYRROL-1-YL)BENZALDEHYDE
• [3-(1H-PYRROL-1-YL)PHENYL]METHANOL
• 3-(2,5-dimethyl-1H-pyrrol-1-yl)benzoic acid
• 2,4-Diphenylpyrrole
• 2-HYDROXY-5-(1 H-PYRROL-1-YL)BENZOIC ACID
• Fendosal