Diiodohydroxyquinoline

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

Diiodohydroxyquinoline
Names
Preferred IUPAC name
5,7-Diiodoquinolin-8-ol
Other names
Diquinol, iodoxin, diiodoquin, amebaquin
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.362
KEGG
MeSH Iodoquinol
PubChem CID
UNII
InChI
  • InChI=1S/C9H5I2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H N
    Key: UXZFQZANDVDGMM-UHFFFAOYSA-N 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
G01AC01 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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 amebicide 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 full mechanism of action is unknown. Iodoquinol is used for diseases caused by moderate intestinal amebiasis.

Diodoquin enhances zinc absorption in the zinc deficiency disorder Acrodermatitis enteropathica, probably because Diodoquin act as a zinc ionophore.[5]

See also
  • Ionophore

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. Nagata, Noriyuki; Marriott, Deborah; Harkness, John; Ellis, John T.; Stark, Damien (2012). "Current treatment options for Dientamoeba fragilis infections". International Journal for Parasitology: Drugs and Drug Resistance. 2: 204–215. doi:10.1016/j.ijpddr.2012.08.002. ISSN 2211-3207. PMC 3862407. PMID 24533282.
  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.
  5. Aggett, P.J.; Delves, H.T.; Harries, J.T.; Bangham, A.D. (March 1979). "The possible role of Diodoquin as a zinc ionophore in the treatment of acrodermatitis enteropathica". Biochemical and Biophysical Research Communications. 87 (2): 513–517. doi:10.1016/0006-291X(79)91825-4. PMID 375935.
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