Diiodohydroxyquinoline

Diiodohydroxyquinoline

Names
IUPAC name 5,7-diiodoquinolin-8-ol
Other names Diquinol, iodoxin, diiodoquin, amebaquin
Identifiers
CAS Number	83-73-8
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL86754
ChemSpider	3597
ECHA InfoCard	100.001.362
KEGG	D00581
MeSH	Iodoquinol
PubChem	3728
UNII	63W7IE88K8
InChI InChI=1S/C9H5I2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H Key: UXZFQZANDVDGMM-UHFFFAOYSA-N InChI=1/C9H5I2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H Key: UXZFQZANDVDGMM-UHFFFAOYAF
SMILES C1=CC2=C(C(=C(C=C2I)I)O)N=C1
Properties
Chemical formula	C9H5I2NO
Molar mass	396.951
Pharmacology
ATC code	G01AC01 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

The quinoline derivative diiodohydroxyquinoline (INN) or iodoquinol (USAN), can be used in the treatment of amoebiasis.^[1]

It is poorly absorbed from the gastrointestinal tract and is used as a luminal amebicide. It acts by chelation of ferrous ions essential for metabolism.^[2]

It was discovered by Adco Co. and introduced as diiodohydroxyquinoline.^[3]

Susceptibility of Dientamoeba fragilis has been measured.^[4]

Iodoquinol is an amebocide used against Entamoeba histolytica, and it is active against both cyst and trophozoites that are localized in the lumen of the intestine. It is considered the drug of choice for treating asymptomatic or moderate forms of amebiasis. The mechanism of action is unknown. Iodoquinol is used for diseases caused by moderate intestinal amebiasis.

References

1. Ghaskadbi S, Vaidya VG (March 1989). "In vivo antimutagenic effect of ascorbic acid against mutagenicity of the common antiamebic drug diiodohydroxyquinoline". Mutat. Res. 222 (3): 219–22. doi:10.1016/0165-1218(89)90137-7. PMID 2493578.
2. Gideon Online http://web.gideononline.com/web/therapy/index.php?type=drugs&code=20130&view=General. Missing or empty |title= (help)
3. Publishing, William Andrew (2013-01-15). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier Science. p. 1312. ISBN 9780080947266.
4. Chan FT, Guan MX, Mackenzie AM, Diaz-Mitoma F (May 1994). "Susceptibility testing of Dientamoeba fragilis ATCC 30948 with iodoquinol, paromomycin, tetracycline, and metronidazole". Antimicrob. Agents Chemother. 38 (5): 1157–60. doi:10.1128/aac.38.5.1157. PMC 188168. PMID 8067755.