Silodosin

Bezeichnung:Silodosin

CAS-Nr160970-54-7

Englisch Name:Silodosin

CBNumberCB42129460

SummenformelC25H32F3N3O4

Molgewicht495.53

MOL-Datei160970-54-7.mol

Silodosin physikalisch-chemischer Eigenschaften

Schmelzpunkt	>104°C (dec.)
alpha	D25 -14.0° (c = 1.01 in methanol)
Siedepunkt	601.4±55.0 °C(Predicted)
Dichte	1.249±0.06 g/cm3(Predicted)
storage temp.	under inert gas (nitrogen or Argon) at 2–8 °C
Löslichkeit	Aqueous Base (Slightly, Heated Sonicated), DMSO (Slightly, Sonicated), Methanol
pka	14.85±0.10(Predicted)
Aggregatzustand	Solid
Farbe	White to Off-White
InChIKey	PNCPYILNMDWPEY-QGZVFWFLSA-N
SMILES	N1(CCCO)C2=C(C=C(C[C@H](NCCOC3=CC=CC=C3OCC(F)(F)F)C)C=C2C(N)=O)CC1
CAS Datenbank	160970-54-7(CAS DataBase Reference)

Sicherheit

HS Code

29339900

Gefahreninformationscode (GHS)

Silodosin Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Silodosin, an a1A adrenoceptor (a1A-AR) antagonist selective for prostatic receptors, was launched as an oral treatment for dysuria associated with benign prostatic hypertrophy (BPH). The regulation of smooth muscle tone in the bladder neck and prostate is thought to be primarily mediated by a1A-AR. Blockade of these receptors can cause smooth muscle relaxation in these areas, resulting in improved symptoms and urinary flow rates. Conversely, a1B-AR are largely located on vascular smooth muscle, and antagonism of these receptors can cause tissue relaxation and potentially decrease cardiac compensation mechanisms involved in regulating blood pressure.
Chemische Eigenschaften
White Solid
Originator
Kissei (Japan)
Verwenden
Silodosin(Rapaflo) is an α1-adrenoceptor antagonist with high uroselectivity. It causes practically no orthostatic hypotension (in contrast to other α1 blockers). Since Silodosin is a highly selective inhibitor of the α1A adrenergic receptor, it causes pr
Verwenden
An α1a-adrenoceptor antagonist. It is used in treatment of benign prostatic hypertophy.
Verwenden
Silodosin is an α1a-adrenoceptor antagonist. It is used in treatment of benign prostatic hypertrophy.
Definition
ChEBI: Silodosin is an indolecarboxamide.
Trademarks
Urief
Synthese
The synthesis of silodosin has been disclosed in several patents. The latest synthetic route disclosed in the 2006 patent is highlighted in the scheme. The synthesis started with Grignard generation from readily available bromoindoline 65 by treating it with Mg in the presence of a catalytic dibromoethane in THF. After initiation of the reaction with some heat and refluxing at a steady rate, CBZ protected oxazolidinone 66 [39b] was added over 1 h, refluxed for 4 h and then stirred at room temperature for 2 days. The reaction was quenched with 6 M aqueous HCl and stirred for 12 h after which time the reaction was worked up to provide product 67 in 53% yield. Ketone 67 was then treated with triethylsilane in TFA at 0oC and stirred at room temperature for 10 h to provide amine 68 in 61% yield. Bromination of the indoline 68 with bromine in warm acetic acid furnished bromide 69 in 53% yield which was reacted with copper cyanide in DMF at 130oC to give the cyano indoline 70 in 82% yield. Selective deprotection of the benzyloxycarbonyl over the benzyl group was accomplished by reacting indoline 70 with 1 atm hydrogen in the presence of 5% Pd/C in ethanol at room temperature. The resulting free amine 71 was then reacted with mesylate 72 in t-butanol with sodium carbonate as base at 80-90oC for 46 h to provide 73 in 67% yield. Removal of the benzyl ether was accomplished by reacting 73 with 1 atm hydrogen in the presence of 10%Pd/C to give alcohol 74, which upon hydrolysis provided the desired silodosin (X). No yield for the final reaction was given.
target
Adrenergic Receptor
Lager
Store at -20°C

Silodosin Upstream-Materialien And Downstream Produkte

Silodosin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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