基本情報
- CAS
579-38-4- 標準SMILES
CN(C(=O)C(Cl)Cl)c1ccc(O)cc1- InChIKey
GZZZSOOGQLOEOB-UHFFFAOYSA-N- 分子式
- C9H9Cl2NO2
- 平均分子量
- 234.08 g/mol
- 単同位体質量
- 233.0010339
概要
Diloxanide (as [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.
名称と識別子
- 優先名称
- Diloxanide
- IUPAC
- 2,2-dichloro-N-(4-hydroxyphenyl)-N-methylacetamide
- 現地名
- ジロキサニド
- 英語名
- diloxanide
- 分子式
- C9H9Cl2NO2
- 分子量
- 234.08
名称と別名
Diloxanide579-38-4DiloxanidaDiloxanidumAcetamide, 2,2-dichloro-N-(4-hydroxyphenyl)-N-methyl-89134SCM7M2,2-Dichlor-4'-hydroxy-N-methylacetanilidDTXSID0022939RefChem:134130DTXCID502939P01AC01209-439-4
名称をさらに表示
α,α-ジクロロ-4'-ヒドロキシ-N-メチルアセトアニリドジロキサニドα,α-ジクロロ-4′-ヒドロキシ-N-メチルアセトアニリド2,2-ジクロロ-N-(4-ヒドロキシフェニル)-N-メチルアセトアミドRD3803RD-3803diloxanide USP/EP/BPDiloxanide, 10 mM in DMSOα,α-Dichloro-4'-hydroxy-N-methylacetanilide
4-(2,2-dichloro-N-methylacetamido)phenyl furan-2-carboxylate2,2-Dichloro-N-(4-hydroxyphenyl)-N-methylacetamideAmebamidaDiloxanidEntamideAme-bootsRD 38032,2-Dichloro-4'-hydroxy-N-methylacetanilide
データベース識別子
- CAS
579-38-4- PubChem CID
- 11367
- DTXSID
DTXSID0022939- ChEMBL
物性
構造計算による物性
- XLogP
- 2
- 極性表面積
- 40.5 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 2
- 回転可能結合数
- 2
- 重原子数
- 14
- 形式電荷
- 0
- 複雑度
- 203
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
LogP1.78
Human DrugsAntiamoebic and antigiardiasis medicines
物理化学的性質
- 融点
- 175 ° · 175°
- 沸点
- 356.2 · 356.2±42.0 °C(Predicted)
- 比重(密度)
- 1.439 · 1.439±0.06 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · Store at -20°C
- 溶解性
- 33.33 · DMSO:33.33(Max Conc. mg/mL);142.39(Max Conc. mM)
- 外見
- Solid
- 酸解離定数(Pka)
- 9.95 · 9.95±0.15(Predicted)
- 色
- Light brown to brown
化学と産業
薬理情報
ATC Code
P - Antiparasitic products, insecticides and repellents
P01AC01
Pharmacodynamics
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.
Mechanism of ActionUnknown. Diloxanide may inhibit protein synthesis.
Biological Half-Life3 hours
Metabolism/MetabolitesHydrolyzed to furoic acid and diloxanide, which undergoes extensive glucuronidation (99% of diloxanide occurs as glucuronide and 1% as free diloxanide in the systemic circulation).
MeSH Pharmacological ClassificationAgents which are destructive to amebae, especially the parasitic species causing AMEBIASIS in man and animal.
Absorption, Distribution and Excretion
Bioavailability is 90% (in diloxanide parental form), however diloxanide furoate is slowly absorbed from the gastrointestinal tract.
Renal (90%, rapidly excreted as glucuronide metabolite). 10% is excreted in the feces as diloxanide.
応用分野
使用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.
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