Diloxanide

Base Information

• Chemical Name: Diloxanide
• CAS No.: 579-38-4
• Molecular Formula: C9H9 Cl2 N O2
• Molecular Weight: 234.082
• European Community (EC) Number: 209-439-4
• UNII: 89134SCM7M
• DSSTox Substance ID: DTXSID0022939
• Nikkaji Number: J7.430F
• Wikipedia: Diloxanide
• Wikidata: Q81983877
• NCI Thesaurus Code: C65391
• ChEMBL ID: CHEMBL2103768
• Mol file: 579-38-4.mol

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

Chemical Property of Diloxanide

Chemical Property:

• Vapor Pressure: 1.45E-05mmHg at 25°C
• Melting Point: 175°
• Boiling Point: 356.2°C at 760 mmHg
• PKA: 9.95±0.15(Predicted)
• Flash Point: 169.2°C
• PSA: 40.54000
• Density: 1.439g/cm³
• LogP: 2.15870
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 233.0010339
• Heavy Atom Count: 14
• Complexity: 203

Purity/Quality:

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

Diloxanide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C1=CC=C(C=C1)O)C(=O)C(Cl)Cl
• Indications: Diloxanide is the drug of choice in the treatment of asymptomatic passers of cysts of Entamoeba histolytica in non-endemic countries. It is also given after metronidazole treatment to eradicate residual amoeba in the intestine.
• Uses: Diloxanide is used for the treatment of amoebiasis which is an infection of the diegestive tract caused by amoebas of the entamoeba group. Diloxanide is also active against cysts and trophozoites localized in the lumen of the intestine, and it is used for treating the carrier E. histolytica, as well as for treating asymptomatic or moderate forms of amebiasis. In the transition stage to trophozoites, the drug is less active than iodoquinol. A synonym of this drug is furamide.
• Clinical Use: Furamide, or eutamide, is the 2-furoate ester of 2,2-dichloro-4 -hydroxy-N-methylacetanilide. It was developed as a resultof the discovery that various α,α-dichloroacetamidespossessed amebicidal activity in vitro. Diloxanide itself andmany of its esters are also active, and drug metabolism studiesindicate that hydrolysis of the amide is required for theamebicidal effect. Nonpolar esters of diloxanide are morepotent than polar ones. Diloxanide furoate has been used inthe treatment of asymptomatic carriers of E. histolytica. Itseffectiveness against acute intestinal amebiasis or hepaticabscesses, however, has not been established. Diloxanidefuroate is a white crystalline powder. It is administered orallyonly as 500-mg tablets and may be obtained in the UnitedStates from the CDC in Atlanta, Georgia. Asymptomatic intestinal infection with E. histolytica It is also used in invasive amebiasis in conjunction with nitroimidazoles in order to eradicate luminal cysts.

Technology Process of Diloxanide

There total 1 articles about Diloxanide 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:

methanol (67-56-1) + diloxanide furoate (3736-81-0) → 2-furanoic acid (88-14-2) + 2-furoic acid methyl ester (611-13-2) + diloxanide (579-38-4)

Guidance literature:

With phosphate buffer; In acetonitrile; at 40 ℃; pH=9.2; Further Variations:; pH-values; Temperatures; Reagents; Kinetics;

DOI:10.1016/j.farmac.2003.11.015

Reference yield:

diloxanide (579-38-4) + 4-methylsulfonylbenzoyl chloride (40913-92-6) → α,α-Dichlor-N-methyl-p-(4-methylsulfonyl-benzoyloxy)-acetanilid (3686-72-4)

Guidance literature:

In pyridine;

DOI:10.1039/jr9620001420

Reference yield:

diloxanide (579-38-4) + 4-(methylsulfonyl)benzyl bromide (53606-06-7) → α,α-Dichlor-N-methyl-p-(4-methylsulfonyl-benzyloxy)-acetanilid (3614-04-8)

Guidance literature:

With potassium carbonate; In acetone;

DOI:10.1039/jr9620001420

upstream raw materials:

methanol

diloxanide furoate

Downstream raw materials:

α,α-Dichlor-N-methyl-p-(4-methylsulfonyl-benzoyloxy)-acetanilid

α,α-Dichlor-N-methyl-p-(4-methylsulfonyl-benzyloxy)-acetanilid

2,2-Dichloro-N-methyl-N-[4-(1-methyl-5-nitro-1H-imidazol-2-yloxy)-phenyl]-acetamide

Refernces