Diloxanide furoate

Base Information

• Chemical Name: Diloxanide furoate
• CAS No.: 3736-81-0
• Molecular Formula: C₁₄H₁₁Cl₂NO₄
• Molecular Weight: 328.152
• Hs Code.: 2924296000
• European Community (EC) Number: 223-108-1
• NSC Number: 759146
• UNII: YP4N72IW34
• DSSTox Substance ID: DTXSID8048999
• Nikkaji Number: J13.314K
• Wikidata: Q799564
• Metabolomics Workbench ID: 43711
• ChEMBL ID: CHEMBL1334860
• Mol file: 3736-81-0.mol

Synonyms:2,2-dichloro-4'-hydroxy-N-methylacetanilide 2-furoate;2-furamide;diloxanide;diloxanide furoate;entamide furoate;Furamide

Chemical Property of Diloxanide furoate

Chemical Property:

• Vapor Pressure: 6.94E-08mmHg at 25°C
• Melting Point: 111-114 °C
• Refractive Index: 1.6
• Boiling Point: 438.4 °C at 760 mmHg
• PKA: -0?+-.0.50(Predicted)
• Flash Point: 218.9 °C
• PSA: 59.75000
• Density: 1.424 g/cm³
• LogP: 3.26530
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 327.0065132
• Heavy Atom Count: 21
• Complexity: 383

Purity/Quality:

98%,99%, ^*data from raw suppliers

Furamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C1=CC=C(C=C1)OC(=O)C2=CC=CO2)C(=O)C(Cl)Cl
• Uses: selective agonist for delta-opioid receptor Antidiarrhoeals / Antiprotozoles 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.

Technology Process of Diloxanide furoate

There total 4 articles about Diloxanide furoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

C13H9Cl2NO4 + methyl iodide (74-88-4) → diloxanide furoate (3736-81-0)

Guidance literature:

C₁₃H₉Cl₂NO₄; With sodium hydride; In N,N-dimethyl-formamide; paraffin oil; at 0 ℃; for 0.5h;

methyl iodide; In N,N-dimethyl-formamide; paraffin oil; at 0 - 23 ℃; for 18h;

DOI:10.1002/anie.202100801

Reference yield:

N-phenyl-α,α-dichloroacetohydroxamic acid (34282-44-5) → diloxanide furoate (3736-81-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Phenylselenyl bromide / 1,4-dioxane / 18 h / 23 °C

2.1: triethylamine / tetrahydrofuran / 12 h / 0 - 23 °C

3.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil / 0.5 h / 0 °C

3.2: 18 h / 0 - 23 °C

With Phenylselenyl bromide; sodium hydride; triethylamine; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; paraffin oil;

DOI:10.1002/anie.202100801

Reference yield:

N-Phenylhydroxylamine (100-65-2) → diloxanide furoate (3736-81-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydrogencarbonate / diethyl ether / 12 h / 0 - 23 °C

2.1: Phenylselenyl bromide / 1,4-dioxane / 18 h / 23 °C

3.1: triethylamine / tetrahydrofuran / 12 h / 0 - 23 °C

4.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil / 0.5 h / 0 °C

4.2: 18 h / 0 - 23 °C

With Phenylselenyl bromide; sodium hydride; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; N,N-dimethyl-formamide; paraffin oil;

DOI:10.1002/anie.202100801

upstream raw materials:

N-phenyl-α,α-dichloroacetohydroxamic acid

methyl iodide

N-Phenylhydroxylamine

nitrobenzene

Refernces