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% ^*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
• Uses: Cardiac depressant (anti-arrhythmic).
• Clinical Use: Propafenone has been used for acute termination orlong-term suppression of ventricular arrhythmias. It isbound in excess of 95% to 1-acid glycoprotein in theplasma. It is absorbed effectively, but bioavailability is estimatedto be less than 20% because of first-pass metabolism.Less than 1% is eliminated as unchanged drug. Therapywith propafenone may produce effects that can be attributedto both (S) and (R) enantiomers. Thus, the effects may bemodulated because of an enantiomer–enantiomer interactionwhen patients are treated with the racemate.

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

• 1、 Lowes, David J.,Guiguemde, W. Armand,Connelly, Michele C.,Zhu, Fangyi,Sigal, Martina S.,Clark, Julie A.,Lemoff, Andrew S.,Derisi, Joseph L.,Wilson, Emily B.,Guy, R. Kiplin. "Optimization of propafenone analogues as antimalarial leads". supporting information; experimental part. p. 7477 - 7485. Retrieved 2012/01/03.
• 2、 Blaschke, Gottfried,Walther, Bernd. "Optical Resolution of Propafenone and Diprafenone, Configuration of Propafenone Enantiomers". . p. 561 - 564. Retrieved 2007/10/02.