Diloxanide

Diloxanide is a medication used to treat amoeba infections. In places where infections are not common, it is a second line treatment after paromomycin when a person has no symptoms. For people who are symptomatic, it is used after treatment with metronidazole or tinidazole. It is taken by mouth.

Diloxanide
Clinical data
Trade namesFuramide
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration
by mouth
ATC code
Pharmacokinetic data
Bioavailability90% (diloxanide)
MetabolismHydrolyzed to furoic acid and diloxanide, which undergoes extensive glucuronidation
Elimination half-life3 hours
ExcretionKidney (90%), fecal (10%)
Identifiers
  • 4-[(Dichloroacetyl)(methyl)amino]phenyl furan-2-carboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.008.583
Chemical and physical data
FormulaC14H11Cl2NO4
Molar mass328.15 g·mol−1
3D model (JSmol)
Melting point112.5 to 114 °C (234.5 to 237.2 °F)
SMILES
  • O=C(Oc1ccc(N(C(=O)C(Cl)Cl)C)cc1)c2occc2
  • 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
  • Key:BDYYDXJSHYEDGB-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Diloxanide generally has mild side effects. Side effects may include flatulence, vomiting, and itchiness. During pregnancy it is recommended that it be taken after the first trimester. It is a luminal amebicide meaning that it only works on infections within the intestines.

Diloxanide came into medical use in 1956. It is on the World Health Organization's List of Essential Medicines. It is not commercially available in much of the developed world as of 2012.

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