Furosemide

Molecular Structure:

Molecular Formula: C₁₂H₁₁ClN₂O₅S
Molecular Weight: 330.7441
IUPAC Name:  4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoic acid
Synonyms of Furosemide (CAS NO.54-31-9): Furosemide [USAN:INN:JAN] ; Frumil ; 2-Furfurylamino-4-chloro-5-sulfamoylbenzoic acid ; 4-Chloro-5-sulfamoyl-N-furfuryl-anthranilic acid ; 4-Chloro-N-(2-furylmethyl)-5-sulfamoylanthranilic acid ; 4-Chloro-N-furfuryl-5-sulfamoylanthranilic acid ; 5-(Aminosulfonyl)-4-chloro-2-((2-furanylmethyl)amino)benzoic acid ; Aisemide ; Benzoic acid, 5-(aminosulfonyl)-4-chloro-2-((2-furanylmethyl)amino)- ; Chlor-N-(2-furylmethyl)-5-sulfamylanthranilsaeure ; Disemide ; EINECS 200-203-6 ; Golan ; Hydroled ; Jenafusid ; Katlex ; Lasix Retard ; Marsemide ; Novosemide ; Prefemin ; Radisemide ; Selectofur ; Urosemide ; Anthranilic acid, 4-chloro-N-furfuryl-5-sulfamoyl-
CAS NO: 54-31-9
Classification Code: Diuretic ; Diuretics ; Drug / Therapeutic Agent ; Human Data ; Membrane Transport Modulators ; Mutation data ; Natriuretic Agents ; Reproductive Effect ; Sodium Potassium Chloride Symporter Inhibitors ; Tumor data
H bond acceptors: 7
H bond donors: 4
Freely Rotating Bonds: 5
Polar Surface Area: 88.44 Å²
Index of Refraction: 1.657
Molar Refractivity: 75.76 cm³
Molar Volume: 205.8 cm³
Surface Tension: 75.2 dyne/cm
Density: 1.606 g/cm³
Flash Point: 305.9 °C
Enthalpy of Vaporization: 91.55 kJ/mol
Boiling Point: 582.1 °C at 760 mmHg
Vapour Pressure: 2.15E-14 mmHg at 25°C
Melting point: 220 °C
Storage temp: 2-8°C
Appearance: white to light yellow crystal powder
Sensitivity: Light and Air sensitive.
Water solubility: Slightly soluble in water.
Stability: Stable, but light sensitive, air sensitive and hygroscopic. Incompatible with strong oxidizing agents.

 Furosemide (CAS NO.54-31-9) is used as a diuretic and blood pressure reducer and it is sometimes used in the management of severe hypercalcemia in combination with adequate rehydration. As a loop diuretic, Furosemide is used in the treatment of congestive heart failure and edema. Besides, it has also been used to prevent thoroughbred and standardbred race horses from bleeding through the nose during races. And along with some other diuretics, Furosemide(54-31-9) is also included on the World Anti-Doping Agency's banned drug list because of  its alleged use as a masking agent for other drugs.

 Furosemide (CAS NO.54-31-9) is prepared by treating 2,4,5-trichlorobenzoic acid with chlorosulfonic acid, and fur-ther treatment with ammonia and furfuryl amine. Furosemide can also be synthesized stating with 2,4-dichlorobenzoic acid (formed by chlorination and oxidation of toluene). Reaction with chlorosulfonic acid is an electrophilic aromatic substitution via the species -SO,Cl- attacking ortho and para to the chlorines and meta to the carboxylate. Ammonolysis to the sulfonamide is followed by nucleophilic aromatic substitution of the loss hindered chlorine by furfurylamine (obtained from furfural-a product obtained by the hydrolysis of carbohydrates).

Hazard Codes of Furosemide (CAS NO.54-31-9): TF
Risk Statements: 61-39/23/24/25-11
61: May cause harm to the unborn child
39/23/24/25: Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed 
11: Highly Flammable
Safety Statements: 7-16-45-53-36/37/39-22
7: Keep container tightly closed 
16: Keep away from sources of ignition - No smoking 
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
53: Avoid exposure - obtain special instruction before use 
36/37/39: Wear suitable protective clothing, gloves and eye/face protection 
22: Do not breathe dust
RIDADR: UN 1230 3/PG 2
WGK Germany: 3
RTECS: CB2625000

 Furosemide may undergo hydrolysis at sufficiently low pH. The pH of aqueous solutions should be maintained in the basic range to prevent hydrolysis. Alcohol has been shown to improve the stability of Furosemide. Incompatible with strong oxidizing agents .