Alfuzosin

Base Information

• Chemical Name: Alfuzosin
• CAS No.: 81403-80-7
• Deprecated CAS: 128707-53-9,86163-78-2
• Molecular Formula: C19H27N5O4
• Molecular Weight: 389.454
• European Community (EC) Number: 617-230-8
• NSC Number: 760065
• UNII: 90347YTW5F
• DSSTox Substance ID: DTXSID6048549
• Nikkaji Number: J34.501F
• Wikipedia: Alfuzosin
• Wikidata: Q2736873
• NCI Thesaurus Code: C61627
• RXCUI: 17300
• Pharos Ligand ID: 5BLLG4C71Z94
• Metabolomics Workbench ID: 42722
• ChEMBL ID: CHEMBL709
• Mol file: 81403-80-7.mol

Synonyms:Alfetim;alfusozine;alfuzosin;alfuzosin hydrochloride;alphuzosine;Benestan;N-(3-((4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino)propyl)tetrahydro-2-furancarboxamide;Urion;UroXatral;Xatral

Chemical Property of Alfuzosin

Chemical Property:

• Appearance/Colour: White Crystaline Powder
• Melting Point: 178-180 °C
• Refractive Index: 1.62
• PKA: 14.80±0.20(Predicted)
• PSA: 111.83000
• Density: 1.272 g/cm³
• LogP: 2.32280
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Sparingly), Methanol (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 389.20630436
• Heavy Atom Count: 28
• Complexity: 511

Purity/Quality:

99.9% ^*data from raw suppliers

Alfuzosin >98% ^*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: CN(CCCNC(=O)C1CCCO1)C2=NC3=CC(=C(C=C3C(=N2)N)OC)OC
• Recent ClinicalTrials: Uroxatral in Men With Benign Prostate Hypertrophy (BPH) and Erectile Dysfunction (ED)
• Recent EU Clinical Trials: 12-week, multicenter, double-blind, randomized, placebo-controlled, parallel-group
• Description: Alfuzosin hydrochloride is a post-synaptic a-antagonist useful in the symptomatic treatment of benign prostatic hypertrophy and acute adenoma by lowering urethral contractions induced by alpha, stimulation. Alfuzosin is also being developed as an antihypertensive; its efficacy in this indication is comparable to prazosin with no significant change in heart rate.
• Uses: dietary supplement

Technology Process of Alfuzosin

There total 12 articles about Alfuzosin 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: 84.0%

→ alfuzosin (81403-80-7)

Guidance literature:

In isopropyl alcohol; at 50 - 55 ℃; for 0.5 - 0.583333h; Purification / work up;

Reference yield: 81.0%

N-<3-(methylamino)propyl>tetrahydrofuran-2-carboxamide (81403-67-0) + 2-chloro-6,7-dimethoxyquinazolin-4-amine (23680-84-4) → alfuzosin (81403-80-7)

Guidance literature:

With tert-Amyl alcohol; In toluene; at 110 ℃; for 16h; chemoselective reaction; Green chemistry;

DOI:10.1039/c5ra18288c

Reference yield: 73.0%

tetrahydro-2-furancarboxylic acid (16874-33-2) + N1-methyl-N1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1,3-propanediamine (76362-29-3) → alfuzosin (81403-80-7)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 5 ℃; for 1h; Product distribution / selectivity;

upstream raw materials:

N¹-methyl-N¹-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1,3-propanediamine

1-(tetrahydrofuran-2-ylcarbonyl)-1H-imidazole

tetrahydrofuran-2-carbonyl chloride

alfuzosin hydrochloride

Downstream raw materials:

alfuzosin hydrochloride

Refernces

• 1、 -. "METHOD OF PREPARING ANHYDROUS ALFUSOZIN HYDROCHLORIDE". Page/Page column 14. . Retrieved 2010/04/03.
• 2、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF ALFUZOSIN AND ITS NOVEL POLYMORPH". Page/Page column 9-10. . Retrieved 2009/03/07.