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54-31-9 Usage

Efficient diuretics

Furosemide, is a class of efficient sulfonamide diuretics acting on the medullary loop of the ascending branch of the medulla,it has a strong and short-term diuretic effect,which can increase the excretion of water, sodium, chloride, potassium, calcium, magnesium, phosphate and so on. It Mainly inhibits Na + and Cl-reabsorption in medullary and cortex of the medullary loop ascending branch crude segment , it can promote the excretion of sodium, chloride and potassium and affect the formation of renal medullary high osmotic pressure,it can interfer the process of concentration and dilution of urine, and it can increase urine output. This product can inhibit the activity of prostaglandin decomposition enzyme ,make the content of prostaglandin E2 increase,it has effect on expansion of blood vessels, it also plays a role in the proximal tubule, glomerular filtration,it can increase renal blood flow,and adjust renal blood flow distribution,and reduce blood flow so that the cortex surface blood flow increases,it promotes diuresis, its effect is fast and strong, it is used for other diuretics invalid cases. Clinically it is used for the treatment of cardiac edema, renal edema, cirrhosis ascitic fluid, peripheral edema caused by dysfunction or vascular disorders , and it may contribute to an upper urinary tract stones excretion. Administration intravenously can treat brain edema, it also can accelerate the excretion of toxic substances in cerebral edema in poisoning . Note that when the diuretic furosemide is used, since the excretion of urine Cl-, Na +, K +, H + is increasing, while the excretion of HCO3-is not increasing, long-term repeated drug use or large quantities of drugs can cause low salt syndrome, low chlorine and low potassium alkalosis. In recent years, researchers find that inhalation of furosemide can have a significant effect on asthma, it is like cromolyn sodium, which through inhibition of allergic mediator release, it can inhibit the release of the neurotransmitter acetylcholine and substance P, which may be related to inhibiting chloride ions into the cell membranes of respiratory tract. Clinically,it is used in exercise-induced asthma, immediate and delayed type antigen-induced asthma. The above information is edited by the lookchem of Tian Ye.

Chemical properties

white or white alike crystalline powder. 206 ℃ melting point. Dissolved in acetone, methanol, dimethyl formamide, slightly soluble in ethanol, insoluble in water. Odorless, almost tasteless.

Uses

Different sources of media describe the Uses of 54-31-9 differently. You can refer to the following data:
1. The diuretic effect of this product is a strong and short,it is a potent diuretic for the treatment of edema caused by heart, liver, kidney and other diseases, in particular, the base cases which other diuretics are invalid to;it can be used to treat acute pulmonary edema, brain edema , acute renal failure and high blood pressure and other diseases; in combination with fluid infusion, the product can promote poison excretion. Rat oral LD50 is 2600-2820mg/kg.
2. diuretic, antihypertensive
3. Furosemide inhibits ion co-transport in the kidney. Furosemide is used as a diuretic.
4. This compound belongs to the aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
5. An inhibitor of NKCC and a GABAA receptor antagonist.

production method

2,4-dichlorobenzoic acid (see 12740) by sulfochlorination,ammoniation, acidification ,dichloro-5-sulfamoyl-benzoic acid is obtained. Then after condensation with the chaff amine , furosemide is produced.

Category

Toxic substances

Toxicity grading

Middle toxic

Acute toxicity

Oral-rat LD50: 2600 mg/kg; Oral-Mouse LD50: 2200 mg/kg.

Flammability and hazard characteristics

Combustible; fire decomposition produces toxic nitrogen oxides; sulfur oxides and chlorides smoke.

Storage Characteristics

Ventilated, low-temperature ,dry storeroom.

Extinguishing agent

Water, carbon dioxide, dry powder,sandy soil.

Description

Furosemide (Item No. 26298) is an analytical reference standard categorized as a diuretic. Formulations containing diuretics, including furosemide, have been misused in sports for weight reduction and as masking agents in humans and to prevent exercise-induced pulmonary hemorrhage in racehorses. This product is intended for use in analytical forensic applications. This product is also available as a general research tool .

Chemical Properties

white to light yellow crystal powde

Originator

Lasix,Hoechst,W. Germany,1964

Definition

A benzoic-sulfonamide-furan. It is a diuretic with fast onset and short duration and anti-hypertensive agent.

Manufacturing Process

10.8 grams of 3-sulfamyl-4,6-dichlorobenzoic acid (0.04 mol) and 11.7 grams of furfurylamine (0.12 mol) are heated in 30 cc of diethyleneglycoldimethylether for 6 hours under reflux. When pouring the reaction mixture into 300 cc of 1 N hydrochloric acid, the reaction product is immediately separated off in the form of crystals. The light-yellow crude product is purified by dissolving it in 100 cc of warm 1 N sodium bicarbonate solution, precipitation by means of hydrochloric acid and subsequent recrystallization from ethanol/water, with addition of charcoal. Colorless prisms are obtained which decompose at 206°C while adopting a brown coloration, and with evolution of gas.

Brand name

Lasix (Sanofi Aventis).

Therapeutic Function

Diuretic

General Description

Odorless white to slightly yellow crystalline powder. A diuretic drug. Almost tasteless.

Air & Water Reactions

Light sensitive. Air sensitive. Slightly soluble in water.

Reactivity Profile

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 .

Hazard

Poison; moderately toxic; teratogen; questionable carcinogen; mutagen.

Fire Hazard

Flash point data for Furosemide are not available; however, Furosemide is probably combustible.

Biological Activity

Loop diuretic that inhibits the Na + /2Cl - /K + (NKCC) cotransporter. Also acts as a non-competitive antagonist at GABA A receptors with ~ 100-fold greater selectivity for α 6-containing receptors than α 1-containing receptors.

Biochem/physiol Actions

Inhibits ion co-transport in the kidney.

Mechanism of action

Furosemide is a highly effective and quick-acting diuretic whose action, like all of the examined loop diuretics, is associated with blocking reabsorption of ions in the ascending bend of Henle’s loop. It is used for edema syndrome of various origins, edema of the lungs and brain, chronic renal insufficiency, some forms of hypertonic crises, and poisoning by barbiturates and other compounds excreted mainly with urine.

Clinical Use

Furosemide has a saluretic effect 8- to 10-fold that of the thiazide diuretics; however, it has a shorter duration of action (~6–8 hours). Furosemide causes a marked excretion of sodium, chloride, potassium, calcium, magnesium, and bicarbonate ions, with as much as 25% of the filtered load of sodium excreted in response to initial treatment. It is effective for the treatment of edemas connected with cardiac, hepatic, and renal sites. Because it lowers the blood pressure similar to the thiazide derivatives, one of its uses is in the treatment of hypertension.

Side effects

Clinical toxicity of furosemide and other loop diuretics primarily involves abnormalities of fluid and electrolyte balance. As with the thiazide diuretics, hypokalemia is an important adverse effect that can be prevented or treated with potassium supplements or coadministration of potassium-sparing diuretics. Increased calcium ion excretion can be a problem for postmenopausal osteopenic women, and furosemide generally should not be used in these individuals. Hyperuricemia, glucose intolerance, increased serum lipid levels, ototoxicity, and gastrointestinal side effects might be observed as well. Hypersensitivity reactions also are possible with furosemide (a sulfonamide-based drug), and cross-reactivity with other sulfonamide containing drugs is possible.

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. Human systemic effects by intravenous route: change in the sensitivity of the ear to sound, tinnitus, unspecified effects on the heart, constriction of the arteries, a decrease in urine volume, interstitial nephritis, metabolic alkalosis, pulse rate decrease, fall in blood pressure. Ingestion can damage the liver. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental carcinogenic effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of Cl-, NOx, and SOx.

Synthesis

Furosemide, 4-chloro-N-furfuryl-5-sulfamoylanthranylic acid (21.4.11), is synthesized in a relatively simple manner from 2,4-dichlorobenzoic acid, which is converted into 5-aminosulfonyl-4,6-dichlorobenzoic acid (21.4.10) during subsequent reaction with chlorosulfonic acid and ammonia. Reacting this with furfurylamine gives furosemide (21.4.11) .

Veterinary Drugs and Treatments

Furosemide is used for its diuretic activity in all species. It is used in small animals for the treatment of congestive cardiomyopathy, pulmonary edema, hypercalcuric nephropathy, uremia, as adjunctive therapy in hyperkalemia and, occasionally, as an antihypertensive agent. In cattle, it is approved for use for the treatment of post-parturient udder edema. It has been used to help prevent or reduce epistaxis (exercise-induced pulmonary hemorrhage; EIPH) in racehorses.

Drug interactions

Potentially hazardous interactions with other drugs Analgesics: increased risk of nephrotoxicity with NSAIDs; antagonism of diuretic effect with NSAIDs. Anti-arrhythmics: risk of cardiac toxicity with anti-arrhythmics if hypokalaemia occurs; effects of lidocaine and mexiletine antagonised. Antibacterials: increased risk of ototoxicity with aminoglycosides, polymyxins and vancomycin; avoid with lymecycline. Antidepressants: increased risk of hypokalaemia with reboxetine; enhanced hypotensive effect with MAOIs; increased risk of postural hypotension with tricyclics. Antiepileptics: increased risk of hyponatraemia with carbamazepine; effects antagonised by phenytoin. Antifungals: increased risk of hypokalaemia with amphotericin. Antihypertensives: enhanced hypotensive effect; increased risk of first dose hypotensive effect with alpha-blockers; increased risk of ventricular arrhythmias with sotalol if hypokalaemia occurs. Antipsychotics: increased risk of ventricular arrhythmias with amisulpride or pimozide (avoid with pimozide) if hypokalaemia occurs; enhanced hypotensive effect with phenothiazines. Atomoxetine: hypokalaemia increases risk of ventricular arrhythmias. Cardiac glycosides: increased toxicity if hypokalaemia occurs. Ciclosporin: variable reports of increased nephrotoxicity, ototoxicity and hepatotoxicity. Cytotoxics: concentration of furosemide increased by dasabuvir, ombitasvir and paritaprevir - reduce furosemide dose; increased risk of ventricular arrhythmias due to hypokalaemia with arsenic trioxide; increased risk of nephrotoxicity and ototoxicity with platinum compounds. Lithium: risk of toxicity.

Metabolism

Little biotransformation of furosemide takes place. It is mainly eliminated via the kidneys (80-90%); a small fraction of the dose undergoes biliary elimination and 10-15% of the activity can be recovered from the faeces.

references

[1]. hochman dw. the extracellular space and epileptic activity in the adult brain: explaining the antiepileptic effects of furosemide and bumetanide. epilepsia, 2012, 53 suppl 1: 18-25. [2]. chen h, sun d. the role of na-k-cl co-transporter in cerebral ischemia. neurol res, 2005, 27(3): 280-286.[3]. prandota j. furosemide: progress in understanding its diuretic, anti-inflammatory, and bronchodilating mechanism of action, and use in the treatment of respiratory tract diseases. am j ther, 2002, 9(4): 317-328.

Check Digit Verification of cas no

The CAS Registry Mumber 54-31-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 4 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 54-31:
(4*5)+(3*4)+(2*3)+(1*1)=39
39 % 10 = 9
So 54-31-9 is a valid CAS Registry Number.
InChI:InChI=1/C12H11ClN2O5S/c13-9-5-10(15-6-7-2-1-3-20-7)8(12(16)17)4-11(9)21(14,18)19/h1-5,15H,6H2,(H,16,17)(H2,14,18,19)

54-31-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Sigma-Aldrich

  • (PHR1057)  Furosemide  pharmaceutical secondary standard; traceable to USP, PhEur and BP

  • 54-31-9

  • PHR1057-1G

  • 804.73CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001493)  Furosemide for peak identification  European Pharmacopoeia (EP) Reference Standard

  • 54-31-9

  • Y0001493

  • 1,880.19CNY

  • Detail
  • USP

  • (1287008)  Furosemide  United States Pharmacopeia (USP) Reference Standard

  • 54-31-9

  • 1287008-200MG

  • 4,662.45CNY

  • Detail

54-31-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name furosemide

1.2 Other means of identification

Product number -
Other names Furosemide,5-(Aminosulfonyl)-4-chloro-2-([2-furanylmethyl]amino)benzoicacid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:54-31-9 SDS

54-31-9Synthetic route

2-Chloromethylfuran
617-88-9

2-Chloromethylfuran

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

4-chloro-5-sulfamoylanthranilic acid

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

Conditions
ConditionsYield
With potassium bromide In N,N-dimethyl-formamide at 120℃; for 24h; Reagent/catalyst; Solvent; Temperature;97%
methyl 4-chloro-2-[((furan-2-yl)methyl)amino]-5-sulfamoylbenzoate
4793-48-0

methyl 4-chloro-2-[((furan-2-yl)methyl)amino]-5-sulfamoylbenzoate

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

Conditions
ConditionsYield
With water; sodium hydroxide In ethanol at 20℃;88.5%
furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

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

2,4-dichloro-5-sulfamoylbenzoic acid

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

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

Furosemide glucuronide

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

Conditions
ConditionsYield
With bile at 37℃; Kinetics; Further Variations:; Reagents; Decomposition;
2,4-dichloro-5-sulfamoylbenzoic acid
2736-23-4

2,4-dichloro-5-sulfamoylbenzoic acid

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

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

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

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

Conditions
ConditionsYield
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

C36H47Br2ClN2O13S

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

Conditions
ConditionsYield
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;
4-chloro-2-fluoro-5-chlorosulfonylbenzoic acid
56447-54-2

4-chloro-2-fluoro-5-chlorosulfonylbenzoic acid

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

Conditions
ConditionsYield
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
4-chloro-2-fluorobenzoic acid
446-30-0

4-chloro-2-fluorobenzoic acid

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

Conditions
ConditionsYield
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
furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

4-chloro-2-fluoro-5-sulfamoylbenzoic acid
4793-22-0

4-chloro-2-fluoro-5-sulfamoylbenzoic acid

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In 1,2-dimethoxyethane at 130℃; for 16h;126 mg
ethyl bromoacetate
105-36-2

ethyl bromoacetate

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

ethyl 2-{4-chloro-2-[(furan-2-ylmethyl)amino]-5-sulfamoylbenzoyloxy} acetate

ethyl 2-{4-chloro-2-[(furan-2-ylmethyl)amino]-5-sulfamoylbenzoyloxy} acetate

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 16h;93%
With potassium carbonate In N,N-dimethyl-formamide at 0 - 30℃; for 1h;73%
methanol
67-56-1

methanol

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

4-chloro-2-[(2,5-dimethoxy-2,5-dihydro-furan-2-ylmethyl)-amino]-5-sulfamoyl-benzoic acid
1351169-05-5

4-chloro-2-[(2,5-dimethoxy-2,5-dihydro-furan-2-ylmethyl)-amino]-5-sulfamoyl-benzoic acid

Conditions
ConditionsYield
With N,N,N,N-tetraethylammonium tetrafluoroborate; ammonium bromide at 20℃; Electrochemical reaction;91%
ethylamine
75-04-7

ethylamine

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

N-ethyl 5-aminosulfonyl-4-chloro-2-[(2-furanylmethyl)amino]benzamide
1236290-43-9

N-ethyl 5-aminosulfonyl-4-chloro-2-[(2-furanylmethyl)amino]benzamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;90%
4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid
54-31-9

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

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

methyl 4-chloro-2-[((furan-2-yl)methyl)amino]-5-sulfamoylbenzoate

Conditions
ConditionsYield
at 25℃; under 760.051 Torr; for 24h;89%
2,2'-dimethyl-[1,1'-biphenyl]iodonium trifluoromethanesulfonate salt

2,2'-dimethyl-[1,1'-biphenyl]iodonium trifluoromethanesulfonate salt

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

C26H22ClIN2O5S

C26H22ClIN2O5S

Conditions
ConditionsYield
With copper diacetate; sodium carbonate; (3aR,3a'R,8aS,8a'S)-2,2'-(propane-2,2-diyl)bis(8,8a-dihydro-3aH-indeno[1,2-d]oxazole) In dichloromethane; water at 30℃; for 12h; enantioselective reaction;88%
tert-Butyl acrylate
1663-39-4

tert-Butyl acrylate

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

(E)-2-(((5-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)furan-2-yl)methyl)amino)-4-chloro-5-sulfamoylbenzoic acid

(E)-2-(((5-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)furan-2-yl)methyl)amino)-4-chloro-5-sulfamoylbenzoic acid

Conditions
ConditionsYield
With 4-(ethylthio)-N,N-dimethylaniline; palladium diacetate; acetic acid; hydroquinone at 60℃; for 3h; Reagent/catalyst;86%
4-nitrooxy-piperidine, nitric acid salt
104963-86-2

4-nitrooxy-piperidine, nitric acid salt

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

2-chloro-4-((furan-2-ylmethyl)amino)-5-((4-(nitrooxy)piperidyl)carbonyl)benzenesulfonamide

2-chloro-4-((furan-2-ylmethyl)amino)-5-((4-(nitrooxy)piperidyl)carbonyl)benzenesulfonamide

Conditions
ConditionsYield
Stage #1: 4-nitrooxy-piperidine, nitric acid salt; 4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid With triethylamine In dimethyl sulfoxide; ethyl acetate at 20℃; for 0.166667h;
Stage #2: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide; ethyl acetate at 20℃;
85%
4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid
54-31-9

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

5-(azidosulfonyl)-4-chloro-2-((furan-2-ylmethyl)amino)benzoic acid
1609375-62-3

5-(azidosulfonyl)-4-chloro-2-((furan-2-ylmethyl)amino)benzoic acid

Conditions
ConditionsYield
With 3-azidosulfonyl-3H-imidazole-1-ium hydrogen sulfate; potassium carbonate In water; isopropyl alcohol at 20℃; for 18h;82%
chloromethyl isobutyrate
61644-18-6

chloromethyl isobutyrate

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

4-Chloro-2-[(furan-2-ylmethyl)-amino]-5-sulfamoyl-benzoic acid isobutyryloxymethyl ester
143417-85-0

4-Chloro-2-[(furan-2-ylmethyl)-amino]-5-sulfamoyl-benzoic acid isobutyryloxymethyl ester

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide Ambient temperature;80%
morpholine
110-91-8

morpholine

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

NTP-1030
1236290-45-1

NTP-1030

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 55℃; for 0.5h;80%
benzyl chloride
100-44-7

benzyl chloride

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

benzyl 4-chloro-2-((3-furanylmethyl)amino)-5-sulfamoylbenzoate

benzyl 4-chloro-2-((3-furanylmethyl)amino)-5-sulfamoylbenzoate

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 80℃; for 12h;78%
methanol
67-56-1

methanol

zinc(II) chloride
7646-85-7

zinc(II) chloride

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

C26H26Cl2N4O12S2Zn

C26H26Cl2N4O12S2Zn

Conditions
ConditionsYield
With sodium hydroxide at 20℃; for 3.5h;77%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

2,2,6,6-tetramethylpiperidin-1-ol
7031-93-8

2,2,6,6-tetramethylpiperidin-1-ol

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

C30H39N3O7S

C30H39N3O7S

Conditions
ConditionsYield
With 2,6-di(t-butyl)-4-phenylphenol; caesium carbonate In dimethyl sulfoxide at 20℃; for 20h; Irradiation; Inert atmosphere;77%
p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

4-methoxybenzyl 5-aminosulfonyl-4-chloro-2-[(2-furanylmethyl)amino]benzoate
1236290-39-3

4-methoxybenzyl 5-aminosulfonyl-4-chloro-2-[(2-furanylmethyl)amino]benzoate

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 60 - 75℃;76%
B(C3HN2(CH3)(C(CH3)3))3ZnOH

B(C3HN2(CH3)(C(CH3)3))3ZnOH

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

ZnB(C3HN2(CH3)(C(CH3)3))3(C6H2(H2NSO2)(COO)(NHCH2(C4H3O))(Cl))

ZnB(C3HN2(CH3)(C(CH3)3))3(C6H2(H2NSO2)(COO)(NHCH2(C4H3O))(Cl))

Conditions
ConditionsYield
In methanol; dichloromethane; water stirred at room temp. for 1 d in a solvent mixture of CH2Cl2/CH3OH/H2O=10/8/3; solvent removed in vac.; recrystd. (methanol) at -25°C; elem. anal.;72%
chloromethyl hexanoate
66542-51-6

chloromethyl hexanoate

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

hexanoyloxymethyl 4-chloro-N-furfuryl-5-sulfamoylanthranilate
143417-81-6

hexanoyloxymethyl 4-chloro-N-furfuryl-5-sulfamoylanthranilate

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide Ambient temperature;71%
chloromethyl n-butyrate
33657-49-7

chloromethyl n-butyrate

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

4-Chloro-2-[(furan-2-ylmethyl)-amino]-5-sulfamoyl-benzoic acid butyryloxymethyl ester
143417-84-9

4-Chloro-2-[(furan-2-ylmethyl)-amino]-5-sulfamoyl-benzoic acid butyryloxymethyl ester

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide Ambient temperature;68%
(tris(3-cumenyl-5-methylpyrazolyl)borate)ZnOH

(tris(3-cumenyl-5-methylpyrazolyl)borate)ZnOH

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

ZnB(C3HN2(CH3)(C6H4CH(CH3)2))3(C6H2(H2NSO2)(COO)(NHCH2(C4H3O))(Cl))

ZnB(C3HN2(CH3)(C6H4CH(CH3)2))3(C6H2(H2NSO2)(COO)(NHCH2(C4H3O))(Cl))

Conditions
ConditionsYield
In methanol; dichloromethane; water stirred at room temp. for 1 d in a solvent mixture of CH2Cl2/CH3OH/H2O=10/8/3; solvent removed in vac.; recrystd. (methanol) at -25°C; elem. anal.;67%
2-phenylethanol
60-12-8

2-phenylethanol

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

2-phenylethyl 5-aminosulfonyl-4-chloro-2-[(2-furanylmethyl)amino]benzoate
1236290-40-6

2-phenylethyl 5-aminosulfonyl-4-chloro-2-[(2-furanylmethyl)amino]benzoate

Conditions
ConditionsYield
Stage #1: 4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 40℃; for 2.5h;
Stage #2: 2-phenylethanol With potassium tert-butylate In tetrahydrofuran for 0.5h;
67%
(R)-1-phenylethanol
1517-69-7

(R)-1-phenylethanol

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

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

(R)-α-methylbenzyl 5-aminosulfonyl-4-chloro-2-[(2-furanylmethyl)amino]benzoate
1236290-41-7

(R)-α-methylbenzyl 5-aminosulfonyl-4-chloro-2-[(2-furanylmethyl)amino]benzoate

Conditions
ConditionsYield
Stage #1: 4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 40℃; for 3h;
Stage #2: (R)-1-phenylethanol With potassium tert-butylate In tetrahydrofuran at 20 - 40℃;
67%
4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid
54-31-9

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

furosemide methyl ester monomethyl sulfonamide
1021869-58-8

furosemide methyl ester monomethyl sulfonamide

Conditions
ConditionsYield
at 25℃; under 760.051 Torr; for 24h;63.8%

54-31-9Relevant articles and documents

Biliary excretion of furosemide glucoronide in rabbits

Sekikawa,Yagi,Oda,Kenmotsu,Takada,Chen,Lin,Benet

, p. 447 - 453 (1995)

Furosemide (F) was administered to rabbits intravenously and intraduodenaly and the biliary excretion was studied. The major metabolite excreted in bile was furosemide glucuronide (FG). P and acyl migration isomers of FG (FG-iso) were also excreted in bile. The biliary excretion rates of total F (F+ PG+FG-iso) following intraduodenal administration of F were much smaller than those following intravenous administration. The fraction of (F+PG-iso) in bile following intraduodenal administration of F were larger than those following intravenous administration. Stability of PG or FG-iso in bile and supernatant solution of the duodenum homogenate of rabbits was studied. FG was unstable in both media and its degradation followed apparent first-order kinetics in both media. In bile, PG degraded to produce several FG-iso and F, while in the supernatant solution of the duodenum homogenate, it hydrolyzed immediately to F. FG-iso were hardly detected in the supernatant solution. These results indicated that FG excreted in bile degraded easily to FG-iso and F. FG might easily hydrolyze to F enzymatically in the duodenum, and the resultant F might be reabsorbed from the intestinal tract. Unabsorbed PG-iso and P might be excreted in the feces.

Furosemide and purification method thereof

-

Page/Page column 0035-0036; 0038, (2021/06/23)

The invention discloses furosemide and a purification method thereof. The furosemide purification method includes the steps of placing a furosemide crude product in an inorganic alkali solution, fully reacting to generate furosemide salt, and conducting recrystallization treatment on the filtrate after decoloration and filtration to obtain purified furosemide salt; and dissolving the purified furosemide salt in purified water, adjusting the pH value of the purified furosemide salt to an acidic condition by using an acid solution, fully hydrolyzing and crystallizing, filtering, and drying to obtain the purified furosemide. Through the mode, the furosemide crude product can be purified only through simple salification and hydrolysis steps, and recrystallization is carried out under the condition of not using an organic solvent, so that the purity and the yield of furosemide are remarkably improved. Meanwhile, the furosemide purification method provided by the invention is simple in process, easy to implement, suitable for industrial large-scale production, capable of effectively improving the production efficiency and relatively good in application prospect.

FUROSEMIDE ANALOGUES AND COMPOSITIONS AND USES THEREOF FOR TREATMENT OF ALZHEIMER'S DISEASE

-

Paragraph 0056; 0059; 0062-0063; 0066-0068, (2021/01/23)

The present application provides furosemide analogues of the general formula Z having activity as anti-Aβ aggregation agents and/or as inhibitors of Aβ induced neuroinflammation. Formula Z These compounds are useful in preventing, delaying and/or treating Alzheimer's Disease. Accordingly, the present application further provides pharmaceutical compositions and method for preventing, delaying and/or treating Alzheimer's Disease.

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