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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/03/27 05:08:18」(JST)
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Diloxanide
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Systematic (IUPAC) name |
4-[(dichloroacetyl)(methyl)amino]phenyl furan-2-carboxylate
|
Clinical data |
Trade names |
Furamide |
AHFS/Drugs.com |
Micromedex Detailed Consumer Information |
Pregnancy
category |
|
Routes of
administration |
Oral |
Legal status |
|
Pharmacokinetic data |
Bioavailability |
90% (diloxanide) |
Metabolism |
Hydrolyzed to furoic acid and diloxanide, which undergoes extensive glucuronidation |
Biological half-life |
3 hours |
Excretion |
Renal (90%), fecal (10%) |
Identifiers |
CAS Number |
3736-81-0 N |
ATC code |
P01AC01 (WHO) |
PubChem |
CID 19529 |
DrugBank |
DB08792 Y |
ChemSpider |
18400 Y |
KEGG |
D02480 Y |
ChEMBL |
CHEMBL1334860 N |
Chemical data |
Formula |
C14H11Cl2NO4 |
Molar mass |
328.147 g/mol |
SMILES
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O=C(Oc1ccc(N(C(=O)C(Cl)Cl)C)cc1)c2occc2
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InChI
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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 Y
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Key:BDYYDXJSHYEDGB-UHFFFAOYSA-N Y
|
NY (what is this?) (verify) |
Diloxanide furoate is a luminal amebicide used in the treatment of amebiasis.[1] It is considered the luminal agent of choice for mild intestinal amebiasis or asymptomatic cyst carriers. It can also be added to metronidazole (active drug in luminal and extraintestinal amebiasis) in acute amebic dysentery as well as hepatic abscess(In hepatic abscess it is for the control of cysts in the lumen which may cause relapse). The drug was discovered by The Boots Company Plc in 1956 and introduced as Furamide. The Furamide brand is now owned by Abbott Laboratories. It is not available in the US. In India it is available as Amicline by Franco-Indian.
It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[2]
Safety and effectiveness
A 13-year study conducted by the United States Center for Disease Control between 1977 and 1990 found that this drug had a low incidence of side effects and was successful in treatment of 86% of asymptomatic carriers of Entamoeba histolytica.[3]
References
- ^ Fernandes H, D'Souza CR, Swethadri GK, Naik CN (2009). "Ameboma of the colon with amebic liver abscess mimicking metastatic colon cancer". Indian J Pathol Microbiol 52 (2): 228–30. doi:10.4103/0377-4929.48927. PMID 19332922.
- ^ "WHO Model List of Essential Medicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
- ^ McAuley JB, Herwaldt BL, Stokes SL; et al. (1992). "Diloxanide furoate for treating asymptomatic Entamoeba histolytica cyst passers: 14 years' experience in the United States". Clin. Infect. Dis. 15 (3): 464–8. doi:10.1093/clind/15.3.464. PMID 1520794.
Antiparasitics – antiprotozoal agents – agents against amoebozoa/amebicide (P01)
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Entamoeba |
Tissue amebicides
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Nitroimidazole derivatives
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- Metronidazole#
- Tinidazole
- Ornidazole
- Nimorazole
- Secnidazole
- Azanidazole
- Propenidazole
|
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Other
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- isoquinoline (Emetine/Dehydroemetine)
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|
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Luminal amebicides
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Hydroxyquinoline derivatives
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- Cl (Chlorquinaldol)
- Br (Tilbroquinol
- Broxyquinoline)
- I (Diiodohydroxyquinoline)
- I, Cl (Clioquinol)
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Dichloroacetamide derivatives
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- Diloxanide#
- Clefamide
- Etofamide
- Teclozan
|
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Aminoglycoside
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|
|
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Other/ungrouped
|
- arsenic (Arsthinol
- Difetarsone
- Glycobiarsol)
- phenanthroline (Phanquinone)
- aminoacridine (Mepacrine)
- quinazoline (Trimetrexate)
- thiazole (Tenonitrozole)
- sesquiterpene (Fumagillin)
|
|
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Acanthamoeba |
- Propamidine
- Chlorhexidine
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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|
UpToDate Contents
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English Journal
- Development of particulate drug formulation against C. parvum: Formulation, characterization and in vivo efficacy.
- Blanco-García E1, Guerrero-Callejas F2, Blanco-Méndez J1, Gómez-Couso H3, Luzardo-Álvarez A4.
- European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.Eur J Pharm Sci.2016 Sep 20;92:74-85. doi: 10.1016/j.ejps.2016.06.023. Epub 2016 Jul 2.
- This research aims towards developing an alternative therapy against Cryptosporidium parvum using bioadhesive paromomycin and diloxanide furoate-loaded microspheres. Microspheres were prepared using chitosan and poly(vinyl alcohol) and two types of cyclodextrins (β-CD and DM-β-CD) for the potentia
- PMID 27381880
- Enhancement of site specific delivery of diloxanide furoate as an antiamoebic drug.
- Tiwari V1, Verma S2, Verma SK3, Dangi JS1.
- European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.Eur J Pharm Sci.2016 Apr 30;86:50-7. doi: 10.1016/j.ejps.2016.03.001. Epub 2016 Mar 4.
- The basic aim of the present research work is to deliver the diloxanide furoate (DF) at specific area using pectin microspheres. The microspheres were prepared by spray drying method and cross-linked by zinc acetate. Different concentrations of polymer (pectin 0.5-3%) and cross-linking agent (0-3% w
- PMID 26952868
Japanese Journal
- 源河 いくみ
- 日本化学療法学会雜誌 = Japanese journal of chemotherapy 54(5), 435-439, 2006-09-10
- … Metronidazole therapy is followed by paromomycin, or diloxanide furoate, which are non absorbed luminal agents that prevent relapse by eradicating residual cysts in the colon. …
- NAID 10018040925
- 外江 由希子,東 克彦,山根 広志,岡田 和久,中村 嘉典,雑賀 明宏,谷本 聡,辻内 和司,高辻 幹雄,岡 久渡,伊藤 秀一,西岡 新吾
- 日本消化器内視鏡学会雑誌 = Gastroenterological endoscopy 39(7), 1260-1264, 1997-07-20
- … Ulcerative lesions were cured with metronidazole and the cysts of amoeba also disappeared in the stool with diloxanide furoate. …
- NAID 10006816058
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