fenspiride Chemical Properties

Boiling point:

126-127 °C(Press: 2 Torr)

Density 

1.19±0.1 g/cm3(Predicted)

pka

12.44±0.20(Predicted)

form 

Solid:particulate/powder

color 

White to off-white

LogP

1.798-1.802 at 20℃ and pH6

fenspiride Usage And Synthesis

Originator

Viarespan,Servier,France,1969

Uses

Bronchodilator;anti-adrenergic (β-receptor).

Definition

ChEBI: 8-(2-phenylethyl)-1-oxa-3,8-diazaspiro[4.5]decan-2-one is an azaspiro compound.

Manufacturing Process

A solution of 192 g of 1-phenethyl-4-hydroxy-4-aminomethyl piperidine in 800 cc of diethylcarbonate is heated for 2? hours to reflux at about 80°C in the presence of sodium methylate (prepared for immediate use from 2 g of sodium). After this time, the ethyl alcohol formed during the reaction is slowly distilled while the maximum temperature is reached. The excess ethyl carbonate is distilled under reduced pressure. A crystallized residue is then obtained, which is stirred with 400 cc of water and 400 cc of ether. The solution is filtered and 125 g (77.6%) of practically pure product melting at 232°C to 233°C, are obtained.
The starting material was prepared in a yield of 58% by reduction of the corresponding cyanohydrin. It in turn was prepared from 1-(2-phenylethyl)-4- piperidone and potassium cyanide to give the cyanohydrin which was reduced by lithium aluminum hydride.

Therapeutic Function

Bronchodilator

Pharmaceutical Applications

Fenspiride is an antagonist of 5-hydroxytryptamine, whose effect on bronchial smooth muscle expansion is between isoproterenol and theophylline. It also has the effect of unobtrusion-free respiratory tract and air resistance elimination in the lungs. It has the effect of antitussive, antipyretic, analgesic and anti-inflammatory, and the antipyretic and analgesic effect is better than aminopyrine and the anti-inflammatory effect is stronger than bute.

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