4-(2,2-dichloro-N-methylacetamido)phenyl furan-2-carboxylate

• ChemBase ID: 6394
• Molecular Formular: C14H11Cl2NO4
• Molecular Mass: 328.14744
• Monoisotopic Mass: 327.0065132
• SMILES: ClC(Cl)C(=O)N(c1ccc(OC(=O)c2occc2)cc1)C
• Canonical SMILES: O=C(N(c1ccc(cc1)OC(=O)c1ccco1)C)C(Cl)Cl
• InChI: InChI=1S/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
• InChIKey: BDYYDXJSHYEDGB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2,2-dichloro-N-methylacetamido)phenyl furan-2-carboxylate
• IUPAC Traditional name: diloxanide furoate; diloxanide
• Synonyms: Diloxanide furoate; Diloxanide; 2,2-Dichloro-N-(4-hydroxyphenyl)-N-methylacetamide 2-furoic acid ester; Diloxanide furoate

Database IDs

• CAS Number: 3736-81-0
• EC Number: 223-108-1
• MDL Number: MFCD00083302
• PubChem SID: 160969701; 24894026
• PubChem CID: 19529

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.090932
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.0782325
• LogD (pH = 7.4): 3.0782318
• Log P: 3.0782325
• Molar Refractivity: 78.2065 cm^3
• Polarizability: 29.89647 Å^3
• Polar Surface Area: 59.75 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.33
• LOG S: -3.93
• Solubility (Water): 3.82e-02 g/l

PROPERTIES

Safety Information

• RTECS: LV1821800
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

DETAILS

DrugBank - DB08792

• Drug Groups: approved
• Description: Diloxanide furoate is an anti-protozoal drug used in the treatment of Entamoeba histolytica and some other protozoal infections. Although it is not currently approved for use in the United States, it was approved by a CDC study in the treatment of 4,371 cases of Entamoeba histolytica from 1977 to 1990.
• Indication: Diloxanide is used alone as a primary agent in the treatment of asymptomatic (cyst passers) intestinal amebiasis caused by Entamoeba histolytica. Diloxanide may also be used concurrently, or sequentially, with other agents such as the nitroimidazoles (eg. metronidazole) in the treatment of invasive or extraintestinal forms of amebiasis.
• Pharmacology: Diloxanide is a luminal amebicide, however the mechanism of action of diloxanide is unknown. Diloxanide destroys the trophozoites of E. histolytica that eventually form into cysts. The cysts are then excreted by persons infected with asymptomatic amebiasis. Diloxanide furoate is a prodrug, and is hydrolyzed in the gastrointestinal tract to produce diloxanide, the active ingredient.
• Affected Organisms: Protozoa
• Biotransformation: Hydrolyzed to furoic acid and diloxanide, which undergoes extensive glucuronidation (99% of diloxanide occurs as glucuronide and 1% as free diloxanide in the systemic circulation).
• Absorption: Bioavailability is 90% (in diloxanide parental form), however diloxanide furoate is slowly absorbed from the gastrointestinal tract.
• Half Life: 3 hours
• Elimination: Renal (90%, rapidly excreted as glucuronide metabolite). 10% is excreted in the feces as diloxanide.
• References: McAuley JB, Herwaldt BL, Stokes SL, Becher JA, Roberts JM, Michelson MK, Juranek DD: Diloxanide furoate for treating asymptomatic Entamoeba histolytica cyst passers: 14 years' experience in the United States. Clin Infect Dis. 1992 Sep;15(3):464-8. [Pubmed]
• External Links: Wikipedia; Drugs.com

REFERENCES

• McAuley JB, Herwaldt BL, Stokes SL, Becher JA, Roberts JM, Michelson MK, Juranek DD: Diloxanide furoate for treating asymptomatic Entamoeba histolytica cyst passers: 14 years' experience in the United States. Clin Infect Dis. 1992 Sep;15(3):464-8. Pubmed