27589-33-9

Basic information

• Product Name: Azosemide
• Synonyms: 2-chloro-5-(1h-tetrazol-5-yl)-4-((2-thienylmethyl)amino)-benzenesulfonamid;2-chloro-5-(1h-tetrazol-5-yl)-n(sup4)-2-thenyl-sulfanilamid;2-chloro-5-(1h-tetrazol-5-yl)-n(sup4)-2-thenylsulfanilamide;5-(4’-chloro-5’-sulfamoyl-2’-thenylaminophenyl)-tetrazole;azosemid;ple1053;AZOSEMIDE;2-chloro-5-(1h-tetrazol-5-yl)-4-(2-thenylamino)benzenesulphonamide
• CAS NO: 27589-33-9
• Molecular Formula: C₁₂H₁₁ClN₆O₂S₂
• Molecular Weight: 370.84
• EINECS: 248-549-7
• Mol File: 27589-33-9.mol
• Article Data: 0

Chemical Properties

• Melting Point: 218-221°
• Boiling Point: 221°C (rough estimate)
• Flash Point: 359.6°C
• Appearance: /
• Density: 1.6843 (rough estimate)
• Vapor Pressure: 7.19E-18mmHg at 25°C
• Refractive Index: 1.6100 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 3.58±0.10(Predicted)
• CAS DataBase Reference: Azosemide(CAS DataBase Reference)
• NIST Chemistry Reference: Azosemide(27589-33-9)
• EPA Substance Registry System: Azosemide(27589-33-9)

Safety Data

• Hazardous Substances Data: 27589-33-9(Hazardous Substances Data)

Usage

Description

Azosemide, also known by the brand name LURET, is a high-ceiling diuretic agent similar in structure and profile to furosemide. It is a sulfonamide derivative with chlorine substitutions at positions 2, 4, and 5, and features a (2-thienylmethyl)amino and 1H-tetrazol-5-yl group. Azosemide is characterized by its diuretic properties and is used in the management of edema and hypertension.

Uses

Used in Pharmaceutical Industry:
Azosemide is used as a diuretic for the treatment of edematous states and hypertension. It helps in the removal of excess fluid from the body, thereby reducing swelling and lowering blood pressure.
Used in Cardiology:
Azosemide is used as a therapeutic agent for the treatment of congestive heart failure and similar edematous conditions. Its diuretic action aids in managing fluid retention and improving the overall cardiovascular health of patients.

Originator

Boehringer Manheim (W. Germany)

Manufacturing Process

The 4-chloro-5-sulfamoyl-2-thenylaminobenzonitrile used as starting material is obtained by the reaction of 4-chloro-2-fluoro-5-sutfamoyl-benzonitrile with thenylamine in anhydrous tetrahydrofuran. Then the 5-(4'-chloro-5'-sulfamoyl-2'-thenylamino)phenyltetrazole (MP 218° to 221°C, yield 37% of theory) is obtained by the reaction of 4-chloro-5- sulfamoyl-2-thenylaminobenzonitrite (MP 170° to 174°C) with sodium azide and ammonium chloride,

Therapeutic Function

Diuretic

Safety Profile

Poison by intraperitoneal andintravenous routes. Moderately toxic by ingestion andsubcutaneous routes. An experimental teratogen. Whenheated to decomposition it emits toxic fumes of Cl-, SOx,and NOx.

InChI:InChI=1/C12H11ClN6O2S2/c13-9-5-10(15-6-7-2-1-3-22-7)8(12-16-18-19-17-12)4-11(9)23(14,20)21/h1-5,15H,6H2,(H2,14,20,21)(H,16,17,18,19)