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

• ChemBase编号: 6394
• 分子式: C14H11Cl2NO4
• 平均质量: 328.14744
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 4-(2,2-dichloro-N-methylacetamido)phenyl furan-2-carboxylate
• IUPAC传统名: diloxanide furoate; diloxanide
• 别名: Diloxanide furoate; Diloxanide; 2,2-Dichloro-N-(4-hydroxyphenyl)-N-methylacetamide 2-furoic acid ester; Diloxanide furoate

登记号

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

理论计算性质

JChem

• Acid pKa: 13.090932
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 3.0782325
• LogD (pH = 7.4): 3.0782318
• Log P: 3.0782325
• 摩尔折射率: 78.2065 cm^3
• 极化性: 29.89647 Å^3
• 极化表面积: 59.75 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.33
• LOG S: -3.93
• 溶解度: 3.82e-02 g/l

分子性质

安全信息

• RTECS编号: LV1821800
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• 安全公开号: 36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

详细说明

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

参考文献

• 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