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Usage

Uses

Used in Pharmaceutical Industry:
Furosemide Related Compound B (100 mg) (4-chloro-5-sulfamoylanthranilic acid) is used as a metabolite for understanding the pharmacokinetics and pharmacodynamics of Furosemide. Studying FUROSEMIDE RELATED COMPOUND B (100 MG) (4-CHLORO-5-SULFAMOYLANTHRANILIC ACID) helps researchers and pharmaceutical companies to optimize the drug's efficacy, safety, and dosing regimens.
Used in Research and Development:
In the field of research and development, Furosemide Related Compound B (100 mg) (4-chloro-5-sulfamoylanthranilic acid) serves as a crucial compound for investigating the metabolic pathways of Furosemide and its potential interactions with other drugs or substances. This knowledge can be applied to develop new drugs or improve existing ones, ultimately benefiting patients with edema and hypertension.
Used in Quality Control and Analysis:
Furosemide Related Compound B (100 mg) (4-chloro-5-sulfamoylanthranilic acid) is utilized in the quality control and analysis of Furosemide-containing pharmaceutical products. By monitoring the presence and concentration of this metabolite, manufacturers can ensure the purity, potency, and consistency of their products, maintaining high standards of quality and safety for consumers.
Used in Toxicology Studies:
In toxicology, Furosemide Related Compound B (100 mg) (4-chloro-5-sulfamoylanthranilic acid) is employed to study the potential adverse effects and toxicity of Furosemide. Understanding the metabolic byproducts and their impact on the body can help researchers identify possible side effects, develop strategies to mitigate them, and improve the overall safety profile of the drug.
Used in Environmental Monitoring:
As a metabolite of Furosemide, Furosemide Related Compound B (100 mg) (4-chloro-5-sulfamoylanthranilic acid) can be found in wastewater and environmental samples. It is used in environmental monitoring to assess the presence and concentration of pharmaceutical compounds in the environment, helping to evaluate the potential ecological impact of these substances and inform strategies for reducing their release into the environment.

Synthesis Reference(s)

The Journal of Organic Chemistry, 27, p. 1383, 1962 DOI: 10.1021/jo01051a062

InChI:InChI=1/C7H7ClN2O4S/c8-4-2-5(9)3(7(11)12)1-6(4)15(10,13)14/h1-2H,9H2,(H,11,12)(H2,10,13,14)

Upstream product

• 54-31-9 4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid 
• 67-56-1 methanol 
• 5900-55-0 N-(5-chloro-2-methylphenyl)acetamide 
• 17560-53-1 6-acetylamino-4-chloro-toluene-3-sulfonic acid amide 
• 17560-54-2 2-acetylamino-4-chloro-5-sulfamoyl-benzoic acid 

Downstream Products

• 34121-17-0 2-Amino-4-chloro-5-sulfamoylbenzamide 
• 21501-33-7 4-chloro-5-sulfamoyl-2-ureido-benzoic acid 
• 108991-98-6 2-ethoxycarbonylamino-4-chloro-5-sulfamoyl-benzoic acid ethyl ester 
• 23380-53-2 7-chloro-2,4-dioxo-1,4-dihydro-2H-benzo[d][1,3]oxazine-6-sulfonic acid amide 
• 75833-13-5 4-Chloro-2-[(furan-2-carbonyl)-amino]-5-sulfamoyl-benzoic acid 

Relevant academic research and scientific papers

Oxidation of fursemide by diperiodatocuprate(III) in aqueous alkaline medium-a kinetic study

Fursemide is the chemical compound 4-chloro-2-(furan-2-ylmethylamino)-5- (aminosulfonyl) benzoic acid. It was oxidized by diperiodatocuprate(III) in alkali solutions, and the oxidation products were identified as furfuraldehyde and 2-amino-4-chloro-5-(aminosulfonyl) benzoic acid. The reaction kinetics were studied spectrophotometrically. The reaction was observed to be first order in [oxidant] and fractional order each in [fursemide] and [periodate], whereas added alkali retarded the rate of reaction. The reactive form of the oxidant was inferred to be [Cu(H3IO6)2]-. A mechanism consistent with the experimental results was proposed, in which oxidant interacts with the substrate to give a complex as a pre-equilibrium state. This complex decomposed in a slow step to give a free radical that was further oxidized by reaction with another molecule of DPC to yield 2-amino-4-chloro-5-(aminosulfonyl) benzoic acid and furfuraldehyde in a fast step. This reaction was studied at 25, 30, 35, 40 and 45∈°C, and the activation parameters E a,ΔH #,ΔS # and ΔG # were determined to be 51 kJ · mol -1,48.5 kJ · mol-1,-63.5 J·K -1· mol-1 and 67 kJ · mol-1, respectively. The value of log∈10 A was calculated to be 6.8.

Identification of furosemide photodegradation products in water-acetonitrile mixture

The aim of this study was to identify the chemical structure of the photodegradation products of furosemide in a water-acetonitrile mixture (1:1). Furosemide solution was irradiated with a D65 fluorescent lamp and the products were isolated by preparative HPLC. The fractions were evaporated to dryness in vacuo. The purity of the photodegradation products was measured by HPLC. The purity of products 1, 3, and 4 was greater than 90%, whereas that of product 2 was 13%, therefore, photodegradation product 2 was unstable. We identified photodegradation products 1 and 3 as 4-chloro-5-sulfamoylanthranilic acid and 4-hydroxy-N-furfuryl-5-sulfamoylanthranilic acid, respectively, by LC/MS and NMR. Additionally, we assumed that photodegradation product 4 was methyl 2-((furan-2-ylmethyl)amino)-4-hydroxy-3-(methyleneamino)-5-sulfamoylbenzoate by LC/MS and NMR. This showed that furosemide underwent hydrolysis and substitution, and reacted with the acetonitrile under the light of a D65 fluorescent lamp. We were furthermore able to determine the elution times of the photodegradation products of furosemide by applying the Japanese Pharmacopoeia chromatographic method for related substances to the isolated products.

Preparative access to transformation products (TPs) of furosemide: A versatile application of anodic oxidation

Furosemide, a pharmaceutical prescribed for the treatment of edema and hypertension, is a known contaminant of water. In this study, chemoselective anodic oxidation was implemented to assist in the identification and the preparation of furosemide transformation products (TPs), i.e., compounds deriving from furosemide and likely to appear in the environment. An aniline and a pyridinium are proposed as plausible TPs and an analytical study of the pyridinium is presented.

DIURETIC COMPOUNDS COMPRISING HETEROCYCLIC NITRIC OXIDE DONOR GROUPS, COMPOSITIONS AND METHODS OF USE

The invention describes novel diuretic compounds comprising at least one heterocyclic nitric oxide donor group, or pharmaccutically acceptable salts thereof, and novel composition comprising at least one diuretic compound comprising at least one heterocyclic nitric oxide donor group, and optionally, at least one nitric oxide enhancing compound and/or at least one therapeutic agent. The invention also provides novel compositions and kits comprising at least one diuretic compound of the invention comprising at least one heterocyclic nitric oxide donor group, and optionally, at least one nitric oxide enhancing compound and/or at least one therapeutic agent. The invention also provides methods for (a) treating conditions resulting from excessive water and/or electrolyte retention; (b) treating cardiovascular diseases; (c) treating renovascular diseases; (d) treating diabetes; (e) treating diseases resulting from oxidatives stress; (f) treating endothelial dysfunctions; (g) treating diseases caused by endothelial dysfunctions; (h) treating cirrhosis; (j) treating pre-eclampsia; (k) treating osteoporosis; (1) treating nephropathy; (m) treating peripheral vascular diseases; (n) treating portal hypertension; (o) treating central nervous system disorders; and (p) treating sexual dysfunctions. The heterocyclic nitric oxide donors are preferably furoxans, sydnonimines, oxatriazole-5-ones and/or oxatriazole-5-imines.

Photolytic degradation of frusemide

Irradiation with 365 nm u.v. light of frusemide (4-chloro-N-furfuryl-5-sulphamoyl-anthranilic acid) in methanol results primarily in photoreduction to N-furfuryl-5-sulphamoylanthranilic acid and photohydrolysis to 4-chloro-5-sulphamoylanthranilic acid (saluamine).