1426173-86-5

Basic information

• Product Name: C₂₅H₂₈⁽²⁾H₄F₃N₃O₄
• CAS NO: 1426173-86-5
• Molecular Weight: 499.51
• Mol File: 1426173-86-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: C₂₅H₂₈⁽²⁾H₄F₃N₃O₄(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₅H₂₈⁽²⁾H₄F₃N₃O₄(1426173-86-5)
• EPA Substance Registry System: C₂₅H₂₈⁽²⁾H₄F₃N₃O₄(1426173-86-5)

Safety Data

• Hazardous Substances Data: 1426173-86-5(Hazardous Substances Data)

Usage

Description

C₂₅H₂₈⁽²⁾H₄F₃N₃O₄, also known as Silodosin-d4, is an isotopic labeled form of Silodosin (S465000). It is an α1a-Adrenoceptor antagonist with a molecular structure that includes 25 carbon atoms, 28 hydrogen atoms, 4 deuterium atoms, 3 fluorine atoms, 3 nitrogen atoms, and 4 oxygen atoms. C₂₅H₂₈⁽²⁾H₄F₃N₃O₄ is characterized by its ability to selectively target and block α1a-adrenergic receptors, which play a role in various physiological processes.

Uses

Used in Pharmaceutical Industry:
Silodosin-d4 is used as a pharmacological tool for the development and evaluation of Silodosin, an α1a-Adrenoceptor antagonist. The application reason for Silodosin-d4 lies in its ability to help researchers understand the mechanism of action, pharmacokinetics, and potential side effects of Silodosin in the treatment of benign prostatic hyperplasia (BPH).
Used in Medical Research:
In the field of medical research, Silodosin-d4 serves as an important research compound for studying the role of α1a-adrenergic receptors in BPH and other related conditions. It aids in the investigation of potential drug interactions, receptor binding specificity, and the development of novel therapeutic strategies for treating BPH and other α1a-adrenergic receptor-mediated disorders.
Used in Drug Development:
Silodosin-d4 is utilized in the drug development process as a reference compound to compare the pharmacological properties of newly synthesized compounds targeting the α1a-adrenergic receptor. This helps in the identification of potential drug candidates with improved efficacy, selectivity, and safety profiles for the treatment of BPH and other related conditions.

Upstream product

• 1051374-60-7 (R)-1-(3-hydroxypropyl)-5-(2-(2-(2-(2,2,2-trifluoro-1-d2-ethoxy)phenoxy)ethyl-d4-amino)propyl)indoline-7-carbonitrile 
• 1051374-62-9 1-methoxy-2-(2,2,2-trifluoro-1-d2-ethoxy)benzene 
• 1051374-63-0 2-(2,2,2-trifluoro-1-d2-ethoxy)phenol 
• 1051374-64-1 1-(2-bromo-d4-ethoxy)-2-(2,2,2-d2-trifluoroethoxy)benzene 
• 1051374-58-3 (R)-1-(3-(benzyloxy)propyl)-5-(2-(2-(2-(2,2,2-trifluoro-1-d2-ethoxy)phenoxy)ethyl-d4-amino)propyl)indoline-7-carbonitrile 
• 90-05-1 2-methoxy-phenol 
• 160968-99-0 2-O-(2,2,2-trifluoroethyl)catechol 
• 239463-72-0 5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile 
• 239463-85-5 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt 

Relevant articles and documents

Synthesis of silodosin glucuronide and its deuterated counterpart: Solving a problematic O-glycosylation of a nitrogen-containing molecule

We report here the first chemical synthesis of silodosin glucuronide, a metabolite of the α1A-adrenoceptor antagonist silodosin, and its deuterium-labeled counterpart. As a key synthetic step, the incorporation of a glucuronosyl unit onto silodosin invariably led to either an undesired orthoester or a complex mixture under an array of standard glycosylation conditions. This problematic O-glycosylation may be attributed to the presence of multiple basic groups that could neutralize the acidic activators, decrease the nucleophilicity of a hydroxy group via hydrogen bond or even facilitate acyl migration side reactions. After elaborate tuning of reaction conditions, success was eventually achieved by using perbenzoylated d-glucuronosyl N-phenyltrifluroacetimidate (PTFA) as donor in combination with a procedure of sequential addition of TMSOTf. This protocol is potentially general for the glycosylation of other nitrogen-containing small molecule drugs.