3736-81-0

Basic information

• Product Name: Diloxanide furoate
• Synonyms: 2,2-DICHLORO-N-(4-HYDROXYPHENYL)-N-METHYLACETAMIDE 2-FUROIC ACID ESTER;DILOXANIDE FUROATE;2-furancarboxylicacid,4-((dichloroacetyl)methylamino)phenylester;2-furoicacid,esterwith2,2-dichloro-4’-hydroxy-n-methylacetanilide;8073cb;amebiazol;dichlofurazol;diclofurazol
• CAS NO: 3736-81-0
• Molecular Formula: C14H11Cl2NO4
• Molecular Weight: 328.15
• EINECS: 223-108-1
• Mol File: 3736-81-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 111-114 °C
• Boiling Point: 438.4 °C at 760 mmHg
• Flash Point: 218.9 °C
• Appearance: /
• Density: 1.424 g/cm³
• Vapor Pressure: 6.94E-08mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: -0?+-.0.50(Predicted)
• CAS DataBase Reference: Diloxanide furoate(CAS DataBase Reference)
• NIST Chemistry Reference: Diloxanide furoate(3736-81-0)
• EPA Substance Registry System: Diloxanide furoate(3736-81-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36
• WGK Germany: 3
• RTECS: LV1821800
• Hazardous Substances Data: 3736-81-0(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 3736-81-0 differently. You can refer to the following data:
1. selective agonist for delta-opioid receptor
2. Antidiarrhoeals / Antiprotozoles
3. Furamide is an ambecide, an anti-protozoal drug used in the treatment of amoebozoa infections.

Indications

Diloxanide furoate (Furamide) is an amebicide that is effective against trophozoites in the intestinal tract. In mild or asymptomatic infections, cures of 83 to 95% have been achieved; in patients with dysentery, cure rates may be less impressive. The drug is administered only orally and is rapidly absorbed from the gastrointestinal tract following hydrolysis of the ester group. It is remarkably free of side effects, but occasionally flatulence, abdominal distention, anorexia, nausea, vomiting, diarrhea, pruritus, and urticaria occur. Diloxanide is excreted in the urine, largely as the glucuronide. It is not available in the United States.

Clinical Use

Diloxanide furoate (available from the Centers for Disease Control and Prevention [CDC]) is prescribed for the treatment of asymptomatic amebiasis but is ineffective as a single agent for the extraintestinal form of the disease. The drug is administered orally and is hydrolyzed in the gut to give diloxanide, which is considered to be the active drug. Diloxanide is the only form identified in the bloodstream. The drug is found in the urine as the glucuronide.

InChI:InChI=1/C14H11Cl2NO4/c1-17(13(18)12(15)16)9-4-6-10(7-5-9)21-14(19)11-3-2-8-20-11/h2-8,12H,1H3

Upstream product

• 34282-44-5 N-phenyl-α,α-dichloroacetohydroxamic acid 
• 74-88-4 methyl iodide 
• 100-65-2 N-Phenylhydroxylamine 
• 98-95-3 nitrobenzene 

Relevant articles and documents

Redox-Neutral Selenium-Catalysed Isomerisation of para-Hydroxamic Acids into para-Aminophenols

A selenium-catalysed para-hydroxylation of N-aryl-hydroxamic acids is reported. Mechanistically, the reaction comprises an N?O bond cleavage and consecutive selenium-induced [2,3]-rearrangement to deliver para-hydroxyaniline derivatives. The mechanism is studied through both 18O-crossover experiments as well as quantum chemical calculations. This redox-neutral transformation provides an unconventional synthetic approach to para-aminophenols.