Basic information
- CAS
579-38-4- Standard SMILES
CN(C(=O)C(Cl)Cl)c1ccc(O)cc1- InChIKey
GZZZSOOGQLOEOB-UHFFFAOYSA-N- Molecular formula
- C9H9Cl2NO2
- Average molar mass
- 234.08 g/mol
- Monoisotopic mass
- 233.0010339
Overview
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.
Names & identifiers
- Preferred name
- Diloxanide
- IUPAC
- 2,2-dichloro-N-(4-hydroxyphenyl)-N-methylacetamide
- English name
- diloxanide
- Molecular formula
- C9H9Cl2NO2
- Molecular weight
- 234.08
Names & synonyms
Diloxanide579-38-4DiloxanidaDiloxanidumAcetamide, 2,2-dichloro-N-(4-hydroxyphenyl)-N-methyl-89134SCM7M2,2-Dichlor-4'-hydroxy-N-methylacetanilidDTXSID0022939RefChem:134130DTXCID502939P01AC01209-439-4
Show more names
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
Database identifiers
- CAS
579-38-4- PubChem CID
- 11367
- DTXSID
DTXSID0022939- ChEMBL
CHEMBL2103768- UNII
- 89134SCM7M
- EC Number
- 209-439-4
- Nikkaji
- J7.430F
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 40.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 203
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP1.78
Human DrugsAntiamoebic and antigiardiasis medicines
Physicochemical properties
- Melting point
- 175 ° · 175°
- Boiling point
- 356.2 · 356.2±42.0 °C(Predicted)
- Density
- 1.439 · 1.439±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 33.33 · DMSO:33.33(Max Conc. mg/mL);142.39(Max Conc. mM)
- form
- Solid
- pka
- 9.95 · 9.95±0.15(Predicted)
- color
- Light brown to brown
- FDA UNII
- 89134 SCM7M · 89134SCM7M
- ATC code
- 1 AC01 · P01AC01
Chemistry & industry
Pharmacology
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.
Applications
UsesDiloxanide 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.
UsesDiloxanide is used for the treatment of amoebiasis which is an infection of the diegestive tract caused by amoebas of the entamoeba group.
Suppliers26 total
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
广东云星生物技术有限公司0751-18902340975/189023400307 18902340307 · [email protected]
北京博奥森生物技术有限公司400-901-9800 18611424007 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
广东翁江化学试剂有限公司0751-2815987 13927875076 · [email protected]
HANGZHOU LEAP CHEM CO., LTD.+86-571-87711850 +86-15355479329 · [email protected]
陕西缔都医药化工有限公司029-029-81120477 17792793610 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
武汉市承天精细化工有限公司18164098996 · [email protected]
常州合晶化工有限公司85528066 13775048983 · [email protected]
BOC Sciences[email protected]
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
上海臻励生物科技有限公司
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…