Alfuzosin Hydrochloride

Base Information

• Chemical Name: Alfuzosin Hydrochloride
• CAS No.: 81403-68-1
• Deprecated CAS: 133880-44-1
• Molecular Formula: C19H27N5O4^.HCl
• Molecular Weight: 425.915
• Hs Code.: 2934990002
• European Community (EC) Number: 620-512-3
• UNII: 75046A1XTN
• DSSTox Substance ID: DTXSID3045514
• Wikidata: Q27114856
• NCI Thesaurus Code: C53408
• RXCUI: 46043
• ChEMBL ID: CHEMBL1723
• Mol file: 81403-68-1.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 Hydrochloride

Chemical Property:

• Appearance/Colour: White to off-white solid
• Vapor Pressure: 3.75E-19mmHg at 25°C
• Melting Point: 225 °C
• Boiling Point: 687.7 °C at 760 mmHg
• PKA: 8.13(at 25℃)
• Flash Point: 369.7 °C
• PSA: 111.83000
• Density: 1.272 g/cm3
• LogP: 3.12480
• Storage Temp.: Store at RT
• Solubility.: DMSO: >10mg/mL
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 425.1829821
• Heavy Atom Count: 29
• Complexity: 511

Purity/Quality:

99% ^*data from raw suppliers

Alfuzosin hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(CCCNC(=O)C1CCCO1)C2=NC3=CC(=C(C=C3C(=N2)N)OC)OC.Cl
• Recent ClinicalTrials: The Effects of α-adrenergic Receptor Antagonists on Choroid and Pupil
• Recent EU Clinical Trials: Etude de l’efficacité et de la tolérance, de l’injection intra prostatique de toxine botulique A, chez l’homme, dans le traitement de l’hyperplasie bénigne de prostate symptomatique.
• Description: Alfuzosin hydrochloride (AFH) is chemically designed as (2RS)-N- [3- [(4-amino-6,7-dimethoxy- quinazolin-2-yl)-methylamino]propyl]oxolane-2-carboxamide hydrochloride. It is a uroselective α1-blocker used for treating benign prostate hyperplasia (BPH). AFH is classified as an adrenergic alpha-1 receptor antagonist with smooth muscle-relaxing activity.
• Uses in Medical Applications: Alfuzosin Hydrochloride binds to post-synaptic alpha-1-adrenoreceptors in smooth muscles of the bladder, prostate, and prostatic urethra, causing relaxation and relieving symptoms of BPH, such as urinary obstruction. It is available in various formulations and has been developed and approved for clinical use as a treatment for BPH. A fixed-dose combination of AFH and solifenacin succinate (SOS) has been formulated for the treatment of both BPH and overactive bladder syndrome (OBS). AFH is an official drug listed in pharmacopeias such as the British Pharmacopeia.
• References: [1] Micellar-enhanced and green-assessed first-derivative synchronous spectrofluorimetric approach for concurrent determination of alfuzosin hydrochloride and solifenacin succinate in different matrices: Docking simulation; DOI 10.1016/j.saa.2023.122442; [2] High ‐ throughput spectrofluorimetric approach for one-step, sensitive, and green assays of alfuzosin hydrochloride using a 96-well microplate reader: Application to tablet formulations and human urine; DOI 10.1016/j.talo.2022.100139; [3] Utilization of a micellar matrix for simultaneous spectrofluorimetric estimation of alfuzosin hydrochloride and vardenafil hydrochloride; DOI 10.1016/j.saa.2021.120420; [4] Stability-indicating HPTLC method for the simultaneous detection and quantification of alfuzosin hydrochloride, solifenacin succinate along with four of their official impurities; DOI 10.1016/j.microc.2020.104905

Technology Process of Alfuzosin Hydrochloride

There total 11 articles about Alfuzosin Hydrochloride 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: 88.0%

alfuzosin (81403-80-7) → alfuzosin hydrochloride (81403-68-1)

Guidance literature:

With hydrogenchloride; In ethanol; at 20 - 25 ℃;

Reference yield: 87.5%

N1-(4-amino-6,7-dimethoxyquinazol-2-yl)-N1-methyl-N2-(tetrahydrofuro-2-yl)propylenediamine (7,7-dimethyl-2-oxo-bicyclo[2,2,1]hept-1-yl)methanesulfonate → alfuzosin hydrochloride (81403-68-1)

Guidance literature:

N₁-(4-amino-6,7-dimethoxyquinazol-2-yl)-N₁-methyl-N₂-(tetrahydrofuro-2-yl)propylenediamine (7,7-dimethyl-2-oxo-bicyclo[2,2,1]hept-1-yl)methanesulfonate; With sodium hydroxide; In dichloromethane; water; at 20 ℃; for 0.5h;

With hydrogenchloride; In ethanol; dichloromethane;

Reference yield: 66.0%

N-<3-(methylamino)propyl>tetrahydrofuran-2-carboxamide (81403-67-0) + 2-chloro-6,7-dimethoxyquinazolin-4-amine (23680-84-4) → alfuzosin hydrochloride (81403-68-1)

Guidance literature:

In i-Amyl alcohol; for 12h; Heating;

DOI:10.1021/jm00151a003

upstream raw materials:

N-<3-(methylamino)propyl>tetrahydrofuran-2-carboxamide

2-chloro-6,7-dimethoxyquinazolin-4-amine

tetrahydro-2-furancarboxylic acid

tetrahydro-N-(3-cyanopropyl)-N-methylfurancarboxamide

Downstream raw materials:

alfuzosin

Refernces

• 1、 -. "A process for the preparation of alfuzosin hydrochloride method (by machine translation)". Paragraph 0023; 0024; 0029; 0042; 0043; 0044-0050. . Retrieved 2017/08/29.
• 2、 -. "Process for the Preparation of Alfuzosin Hydrochloride". Page/Page column 8. . Retrieved 2010/10/19.