| Identification | Back Directory | [Name]
fenspiride | [CAS]
5053-06-5 | [Synonyms]
DESP
FUBMN24
FUB-MN24
Fenspirid
fenspiride
Fenspiridum
Fenspiride-d5
fenspiride USP/EP/BP
8-phenethyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one
Pharmaceutical intermediates BKEDBP BKEDBP bkedbp
8-(2-Phenylethyl)-1-oxa-3,8-diazaspiro[4.5]decan-2-one
1-Oxa-3,8-diazaspiro[4.5]decan-2-one, 8-(2-phenylethyl)- | [EINECS(EC#)]
225-751-3 | [Molecular Formula]
C15H20N2O2 | [MDL Number]
MFCD00867054 | [MOL File]
5053-06-5.mol | [Molecular Weight]
260.34 |
| Chemical Properties | Back Directory | [Boiling point ]
126-127 °C(Press: 2 Torr) | [density ]
1.19±0.1 g/cm3(Predicted) | [form ]
Solid:particulate/powder | [pka]
12.44±0.20(Predicted) | [LogP]
1.798-1.802 at 20℃ and pH6 |
| Hazard Information | Back Directory | [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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