Sotalol

Base Information

• Chemical Name: Sotalol
• CAS No.: 3930-20-9
• Deprecated CAS: 27948-47-6
• Molecular Formula: C₁₂H₂₀N₂O₃S
• Molecular Weight: 272.368
• Hs Code.: 2935009090
• UNII: A6D97U294I
• DSSTox Substance ID: DTXSID0023589
• Nikkaji Number: J10.583J
• Wikipedia: Sotalol
• Wikidata: Q413591
• NCI Thesaurus Code: C61949
• RXCUI: 9947
• Pharos Ligand ID: MWG5WJ5QDVJ3
• Metabolomics Workbench ID: 42834
• ChEMBL ID: CHEMBL471
• Mol file: 3930-20-9.mol

Synonyms:Darob;MJ 1999;MJ-1999;MJ1999;Sotalol;Sotalol Hydrochloride;Sotalol Monohydrochloride

Chemical Property of Sotalol

Chemical Property:

• Appearance/Colour: white crystalline
• Vapor Pressure: 1.22E-08mmHg at 25°C
• Melting Point: 206.5-207 °C
• Refractive Index: 1.57
• Boiling Point: 443.3 °C at 760 mmHg
• PKA: pK1 8.2, pK2 9.8(at 25℃)
• Flash Point: 221.9 °C
• PSA: 86.81000
• Density: 1.24 g/cm³
• LogP: 2.63420
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly, Heated), Methanol (Slightly, Sonicated)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 272.11946368
• Heavy Atom Count: 18
• Complexity: 330

Purity/Quality:

99% ^*data from raw suppliers

Sotalol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Beta-Adrenergic Receptor Antagonists
• Canonical SMILES: CC(C)NCC(C1=CC=C(C=C1)NS(=O)(=O)C)O
• Recent ClinicalTrials: Prospective Evaluation Analysis and Kinetics Registry
• Recent EU Clinical Trials: First-line cryoablation for early treatment of Persistent Atrial Fibrillation – a randomized study comparing early trigger isolation using the Cryoballoon versus antiarrhythmic medication.
• Recent NIPH Clinical Trials: Clinical study of transplacental anti-arrythmic treatment for fetal tachyarrythmias
• Therapeutic Function: Beta-adrenergic blocker, Antiarrhythmic
• Clinical Use: The sotalol enantiomers produce different effects onthe heart. Class III action of d-sotalol in the sinus node isassociated with slowing of sinus heart rate, whereas -adrenergicblockade contributes to the decrease in heart rate observedwith 1- or d,1-sotalol. Sotalol is not metabolized, noris it bound significantly to proteins. Elimination occurs byrenal excretion, with more than 80% of the drug eliminatedunchanged. Sotalol is characteristic of class III antiarrhythmicdrugs, in that it prolongs the duration of the action potentialand, thus, increases the effective refractory period of myocardialtissue. It is distinguished from the other class III drugs(amiodarone and bretylium) because of its -adrenergicreceptor–blocking action.
• Drug interactions: Drugs with inherent QT interval–prolonging activity (i.e., thiazide diuretics and terfenadine) may enhance the class III effects of sotalol.

Technology Process of Sotalol

There total 3 articles about Sotalol 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: 45.0%

4'-(methylsulfonylamino)acetophenone (5317-89-5) → sotalol (3930-20-9,27948-47-6,30236-31-8,30236-32-9)

Guidance literature:

4'-(methylsulfonylamino)acetophenone; With iodine; dimethyl sulfoxide; at 120 ℃;

With isopropylamine; In 1,2-dichloro-ethane; at 25 ℃; for 2h;

With sodium tetrahydroborate; In 1,2-dichloro-ethane; at 0 ℃; for 2h;

Reference yield:

4'-(Isopropylaminoacetyl)-methansulfonanilid-hydrochlorid (5576-49-8) → sotalol (3930-20-9,27948-47-6,30236-31-8,30236-32-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1021/jm00319a023

Reference yield:

→ sotalol (3930-20-9,27948-47-6,30236-31-8,30236-32-9)

Guidance literature:

upstream raw materials:

4'-(Isopropylaminoacetyl)-methansulfonanilid-hydrochlorid

4'-(methylsulfonylamino)acetophenone

Refernces

• 1、 -. "THERAPY FOR COMPLICATIONS OF DIABETES". . . Retrieved 2009/07/02.
• 2、 -. "FLUORESCENCE BASED DETECTION OF SUBSTANCES". . . Retrieved 2009/09/28.