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Basic Information

Molecular Structure:
CAS No.:	54-31-9
Name:	Furosemide
Article Data:	18

Formula:	C₁₂H₁₁ClN₂O₅S
Molecular Weight:	330.749
Synonyms:	Frumide;Urex-M;Diurin;Uritol;Frusedan;Prefemin;5-(Aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoic acid;Depix;Mirfat;Furosix;Aquarid;Chlor-N- (2-furylmethyl)-5-sulfamylanthranilsaeure;Bioretic;4-chloro-2-(2-furylmethylamino)-5-sulfamoyl-benzoic acid;Neo-renal;Furosifar;Puresis;Furosan;Furex;Rusyde;Jenafusid;Aldic;Urian;Furanthril;
EINECS:	200-203-6
Density:	1.606 g/cm³
Melting Point:	220 °C
Boiling Point:	582.1 °C at 760 mmHg
Flash Point:	305.9 °C
Solubility:	Soluble in acetone, DMF or methanol. Slightly soluble in water
Appearance:	white to light yellow crystal powder
Hazard Symbols:	T, F, Xi
Risk Codes:	61-39/23/24/25-11
Safety:	7-16-45-53-36/37/39-22
Transport Information:	UN 1230 3/PG 2
PSA:	131.01000
LogP:	3.74480

Synthetic route

: 617-88-9
2-Chloromethylfuran

: 3086-91-7
4-chloro-5-sulfamoylanthranilic acid

: 54-31-9
4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

Conditions

Conditions	Yield
With potassium bromide In N,N-dimethyl-formamide at 120℃; for 24h; Reagent/catalyst; Solvent; Temperature;	97%

: 4793-48-0
methyl 4-chloro-2-[((furan-2-yl)methyl)amino]-5-sulfamoylbenzoate

: 54-31-9
4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

Conditions

Conditions	Yield
With water; sodium hydroxide In ethanol at 20℃;	88.5%

: 617-89-0
furan-2-ylmethanamine

: 2736-23-4
2,4-dichloro-5-sulfamoylbenzoic acid

: 54-31-9
4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In dimethyl sulfoxide at 130℃; for 6h; Solvent; Inert atmosphere;	71.2%

: Furosemide glucuronide

: 54-31-9
4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

Conditions

Conditions	Yield
With bile at 37℃; Kinetics; Further Variations:; Reagents; Decomposition;

: Furosemide glucuronide

A: 6556-12-3, 489-91-8, 528-16-5, 552-12-5, 577-46-8, 643-33-4, 2240-07-5, 6294-16-2, 10133-02-5, 18402-78-3, 18968-14-4, 21179-08-8, 23018-83-9, 33599-45-0, 33599-46-1, 46171-67-9, 46171-69-1, 46172-26-3, 70021-34-0, 71031-08-8, 104195-06-4, 106499-29-0, 124817-72-7
D-glucuronic acid

B: 54-31-9
4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

Conditions

Conditions	Yield
With water at 37℃; Kinetics; Further Variations:; pH-values; Hydrolysis;

: 2736-23-4
2,4-dichloro-5-sulfamoylbenzoic acid

: 54-31-9
4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium ethanolate; pyrographite / ethanol / 2 h / 40 °C 2.1: ethylene glycol / 3 h / 130 - 135 °C 3.1: water / 0.5 h / 65 °C 3.2: 3 h / 0 - 5 °C / pH 3.5 - 4 View Scheme

: 41733-55-5
4-chloro-N-(2-furfuryl)-5-sulfamoylanthranilic acid sodium salt

: 54-31-9
4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

Conditions

Conditions	Yield
Stage #1: 4-chloro-N-(2-furfuryl)-5-sulfamoylanthranilic acid sodium salt In water at 65℃; for 0.5h; Stage #2: With acetic acid In water at 0 - 5℃; for 3h; pH=3.5 - 4;

: C36H47Br2ClN2O13S

: 54-31-9
4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

Conditions

Conditions	Yield
Stage #1: C36H47Br2ClN2O13S With N-ethyl-N,N-diisopropylamine In water; acetonitrile for 1.25h; Sonication; Stage #2: In water; acetonitrile at 20℃; for 72h; Reagent/catalyst; Temperature;

: 56447-54-2
4-chloro-2-fluoro-5-chlorosulfonylbenzoic acid

: 54-31-9
4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; ammonia / tetrahydrofuran / 16 h / 0 - 20 °C 2: N-ethyl-N,N-diisopropylamine / 1,2-dimethoxyethane / 16 h / 130 °C View Scheme

: 446-30-0
4-chloro-2-fluorobenzoic acid

: 54-31-9
4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: chlorosulfonic acid / 0 - 140 °C 2: triethylamine; ammonia / tetrahydrofuran / 16 h / 0 - 20 °C 3: N-ethyl-N,N-diisopropylamine / 1,2-dimethoxyethane / 16 h / 130 °C View Scheme

Downstream Products

78846-76-1

110-17-8

3086-91-7

396-01-0

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Chemistry

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.

Uses

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.

Production

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).

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD50	intravenous	> 400mg/kg (400mg/kg)		Drugs in Japan Vol. 6, Pg. 725, 1982.
dog	LD50	oral	2gm/kg (2000mg/kg)		Drugs in Japan Vol. 6, Pg. 725, 1982.
human	TDLo	intravenous	1300ug/kg (1.3mg/kg)	CARDIAC: OTHER CHANGES VASCULAR: REGIONAL OR GENERAL ARTERIOLAR CONSTRICTION	Annals of Internal Medicine. Vol. 103, Pg. 1, 1985.
infant	TDLo	intravenous	1mg/kg/4H-I (1mg/kg)		Archives of Disease in Childhood. Vol. 59, Pg. 907, 1984.
man	TDLo	intravenous	29mg/kg (29mg/kg)	SENSE ORGANS AND SPECIAL SENSES: CHANGE IN ACUITY: EAR SENSE ORGANS AND SPECIAL SENSES: TINNITUS: EAR KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED	New England Journal of Medicine. Vol. 282, Pg. 1413, 1970.
mouse	LD50	intravenous	308mg/kg (308mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 14, Pg. 44, 1964.
mouse	LD50	oral	2gm/kg (2000mg/kg)		European Patent Application. Vol. #0008367,
mouse	LD50	unreported	900mg/kg (900mg/kg)		European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 15, Pg. 386, 1980.
rabbit	LD50	intravenous	400mg/kg (400mg/kg)		Drugs in Japan Vol. 6, Pg. 725, 1982.
rabbit	LD50	oral	800mg/kg (800mg/kg)		Drugs in Japan Vol. 6, Pg. 725, 1982.
rat	LD50	intraperitoneal	800mg/kg (800mg/kg)		Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 42, Pg. 199, 1985.
rat	LD50	intravenous	800mg/kg (800mg/kg)		Drugs in Japan Vol. 6, Pg. 725, 1982.
rat	LD50	oral	2600mg/kg (2600mg/kg)		Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat	LD50	subcutaneous	4600mg/kg (4600mg/kg)		Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
women	TDLo	intravenous	2500ug/kg/2M- (2.5mg/kg)	CARDIAC: PULSE RATE	Intensive Care Medicine. Vol. 12, Pg. 54, 1986.
women	TDLo	oral	6250ug/kg (6.25mg/kg)	BEHAVIORAL: MUSCLE WEAKNESS	Journal of Toxicology, Clinical Toxicology. Vol. 31, Pg. 341, 1993.
women	TDLo	oral	120mg/kg/21W- (120mg/kg)	KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS	Journal of the Royal Society of Medicine. Vol. 79, Pg. 239, 1986.

Safety Profile

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

Specification

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 .