Silodosin

Base Information

• Chemical Name: Silodosin
• CAS No.: 160970-54-7
• Molecular Formula: C25H32F3N3O4
• Molecular Weight: 495.542
• Hs Code.: 29339900
• European Community (EC) Number: 814-909-2
• UNII: CUZ39LUY82
• DSSTox Substance ID: DTXSID40167045
• Nikkaji Number: J786.452C
• Wikipedia: Silodosin
• Wikidata: Q411770
• NCI Thesaurus Code: C81372
• RXCUI: 720825
• Pharos Ligand ID: BJBJAP4NP94V
• Metabolomics Workbench ID: 149678
• ChEMBL ID: CHEMBL24778
• Mol file: 160970-54-7.mol

Synonyms:1-(3-hydroxypropyl)-5-(2-(2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethylamino)propyl)indoline-7-carboxamide;KMD 3213;KMD-3213;rapaflo;silodosin

Chemical Property of Silodosin

Chemical Property:

• Appearance/Colour: White to off-white solid
• Vapor Pressure: 2.58E-15mmHg at 25°C
• Refractive Index: 1.552
• Boiling Point: 601.4 °C at 760 mmHg
• PKA: 14.85±0.10(Predicted)
• Flash Point: 317.5 °C
• PSA: 97.05000
• Density: 1.249 g/cm³
• LogP: 4.22730
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Aqueous Base (Slightly, Heated Sonicated), DMSO (Slightly, Sonicated), Methanol
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 13
• Exact Mass: 495.23449100
• Heavy Atom Count: 35
• Complexity: 654

Purity/Quality:

99%, ^*data from raw suppliers

Silodosin-d4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Benign Prostatic Hypertrophy Agents
• Canonical SMILES: CC(CC1=CC2=C(C(=C1)C(=O)N)N(CC2)CCCO)NCCOC3=CC=CC=C3OCC(F)(F)F
• Isomeric SMILES: C[C@H](CC1=CC2=C(C(=C1)C(=O)N)N(CC2)CCCO)NCCOC3=CC=CC=C3OCC(F)(F)F
• Recent ClinicalTrials: Double J Stenting and Sildosin After URSL for Lower Ureteric Stones
• Recent EU Clinical Trials: Are alpha blockers effective in the treatment of bladder elimination problems in female patients with Multiple Sclerosis?
• Recent NIPH Clinical Trials: Study of efficacy of alpha1AR inhibitors for FBD
• Uses: It can be used for treatment of benign prostatic hyperplasia. Silodosin is an α1a-adrenoceptor antagonist. It is used in treatment of benign prostatic hypertrophy. An α1a-adrenoceptor antagonist. It is used in treatment of benign prostatic hypertophy. 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
• Description: 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.

Technology Process of Silodosin

There total 103 articles about Silodosin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.24%

1-(3-hydroxypropyl)-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (885340-13-6) → silodosin (160970-54-7,2182279-45-2)

Guidance literature:

1-(3-hydroxypropyl)-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indole-7-carbonitrile; With potassium carbonate; In water; pH=9;

With cesium hydroxide; dihydrogen peroxide; In dimethyl sulfoxide; at 20 ℃; for 2h;

Reference yield: 95.57%

N-[(2R)-1-[1-(3-hydroxypropyl)-7-carbamoyl-indoline-5-yl]propan-2-yl]-N-[2-[2-[2,2,2]-trifluoroethoxy]phenoxyethyl]-2-nitrobenzenesulfonamide → silodosin (160970-54-7,2182279-45-2)

Guidance literature:

N-[(2R)-1-[1-(3-hydroxypropyl)-7-carbamoyl-indoline-5-yl]propan-2-yl]-N-[2-[2-[2,2,2]-trifluoroethoxy]phenoxyethyl]-2-nitrobenzenesulfonamide; With 1-dodecylthiol; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h; Inert atmosphere;

With sodium methylate; In methanol; at 20 ℃; for 2h;

Reference yield: 94.0%

1-(3-hydroxypropyl)-5-(2R)-2-{2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}aminopropyl-2,3-dihydro-1H-indole-7-carbonitrile oxalic acid → silodosin (160970-54-7,2182279-45-2)

Guidance literature:

With dihydrogen peroxide; sodium hydroxide; In dimethyl sulfoxide; at 5 - 20 ℃;

upstream raw materials:

1-(3-hydroxypropyl)-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indole-7-carbonitrile

2-methoxy-phenol

benzene-1,2-diol

5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile

Refernces

• 1、 -. "THE MANUFACTURING METHOD OF INTERMEDIATE FOR SYNTHESIS OF SILODOSIN AND THE MANUFACTURING METHOD OF SILODOSIN". Paragraph 0145-0147. . Retrieved 2020/03/31.
• 2、 Liu, Hui,Lv, Fei,Liu, Yuan. "Improved Preparation of Silodosin". . p. 287 - 293. Retrieved 2019/05/17.