Fendosal Property

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

Toxicity

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Fendosal Chemical Properties,Usage,Production

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