Propafenone

Base Information

• Chemical Name: Propafenone
• CAS No.: 54063-53-5
• Deprecated CAS: 107300-59-4
• Molecular Formula: C₂₁H₂₇NO₃
• Molecular Weight: 341.45
• European Community (EC) Number: 258-955-6
• UNII: 68IQX3T69U
• DSSTox Substance ID: DTXSID9045184
• Nikkaji Number: J12.333A
• Wikipedia: Propafenone
• Wikidata: Q662511
• NCI Thesaurus Code: C61909
• RXCUI: 8754
• Pharos Ligand ID: 5L7DAVTH8NGY
• Metabolomics Workbench ID: 43399
• ChEMBL ID: CHEMBL631
• Mol file: 54063-53-5.mol

Synonyms:Apo-Propafenone;Arythmol;Baxarytmon;Cuxafenon;Fenoprain;Hydrochloride, Propafenone;Jutanorm;Nistaken;Norfenon;Pintoform;Prolecofen;Propafenon AL;Propafenon Hexal;Propafenon Minden;Propafenone;Propafenone Hydrochloride;Propafenone Hydrochloride, (R)-Isomer;Propafenone Hydrochloride, (S)-Isomer;Propafenone, (+-)-Isomer;Propafenone, (R)-Isomer;Propafenone, (S)-Isomer;Propamerck;Rythmol;Rytmo-Puren;Rytmogenat;Rytmonorm;SA 79;SA-79;SA79

Chemical Property of Propafenone

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.27E-11mmHg at 25°C
• Melting Point: 171 - 174oC
• Refractive Index: 1.557
• Boiling Point: 519.6 °C at 760 mmHg
• PKA: pKa 9.27 (Uncertain)
• Flash Point: 268 °C
• PSA: 58.56000
• Density: 1.096 g/cm³
• LogP: 3.63230
• Storage Temp.: 2-8°C
• Water Solubility.: 759.9ug/L(22.5 oC)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 341.19909372
• Heavy Atom Count: 25
• Complexity: 368

Purity/Quality:

99.9% ^*data from raw suppliers

Propafenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 46-22
• Safety Statements: 53-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiarrhythmic Agents
• Canonical SMILES: CCCNCC(COC1=CC=CC=C1C(=O)CCC2=CC=CC=C2)O
• Recent ClinicalTrials: Antazoline in Comparison to Propafenone in Pharmacological Cardioversion of Atrial Fibrillation.
• Recent EU Clinical Trials: PREemptive Pharmacogenomic testing for Preventing Adverse drug REactions
• General Description: Propafenone is a class IC antiarrhythmic drug primarily used to treat cardiac arrhythmias, but it also exhibits modulatory effects on multidrug resistance (MDR) in tumor cells by inhibiting P-glycoprotein (PGP)-mediated efflux. Structure-activity relationship studies suggest that its efficacy as an MDR modulator is influenced by lipophilicity, with benzofuran analogs of propafenone showing reduced activity compared to the parent compound, highlighting the importance of structural optimization for PGP inhibition.

Technology Process of Propafenone

There total 7 articles about Propafenone 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:

propafenone (107300-59-4,54063-53-5) → (R)-propafenone (107381-31-7,54063-53-5) + (S)-propafenone (107381-32-8,54063-53-5)

Guidance literature:

With chiralcel OD-H column; In methanol; Resolution of racemate;

DOI:10.1021/jm2005546

Reference yield:

propafenone (107300-59-4,54063-53-5) → (R)-propafenone (107381-31-7,54063-53-5) + (S)-propafenone (107381-32-8,54063-53-5)

Guidance literature:

With chiralcel OD-H column; In methanol; Resolution of racemate;

DOI:10.1021/jm2005546

Reference yield:

(S)-(+)-<<(trifluoromethanesulfonyl)oxy>methyl>oxirane (74748-75-7) + 2'-hydroxy-3-phenylpropiophenone (3516-95-8) → (S)-propafenone (107381-32-8,54063-53-5)

Guidance literature:

With hydrogenchloride; NaH; In tetrahydrofuran; propylamine; ethanol;

upstream raw materials:

propafenone

propylamine

diethyl diazodicarboxylate

2'-hydroxy-3-phenylpropiophenone

Downstream raw materials:

(R)-propafenone

(S)-propafenone

1-{(S)-2-Hydroxy-3-[2-(3-phenyl-propionyl)-phenoxy]-propyl}-3-((R)-1-phenyl-ethyl)-1-propyl-urea

1-{(R)-2-Hydroxy-3-[2-(3-phenyl-propionyl)-phenoxy]-propyl}-3-((R)-1-phenyl-ethyl)-1-propyl-urea

Refernces

Structure-activity relationship studies on benzofuran analogs of propafenone-type modulators of tumor cell multidrug resistance

10.1021/jm960384x

The research focuses on the structure-activity relationship (SAR) studies of benzofuran analogs of propafenone-type modulators aimed at reversing multidrug resistance in tumor cells. The purpose of the study was to understand the structural features required for effective inhibition of P-glycoprotein (PGP), a membrane-bound efflux pump associated with multidrug resistance. The researchers synthesized a series of benzofurylethanolamine analogs and evaluated their activity in vitro using rhodamine-123 efflux studies and daunomycin cytotoxicity assays. The conclusions drawn from the study indicated that there is an excellent correlation between the calculated lipophilicity of the compounds and their multidrug resistance-reversing activity, with the benzofuran analogs generally having lower activity/lipophilicity ratios compared to propafenones. The study also found that the incorporation of the ether oxygen of propafenone into a benzofuran moiety led to a decrease in activity, which could be partially compensated by increasing lipophilicity.

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