Diiodohydroxyquinoline

Last updated
Diiodohydroxyquinoline
Iodoquinol.png
Iodoquinol 3D ball.png
Names
Preferred IUPAC name
5,7-Diiodoquinolin-8-ol
Other names
Diquinol, iodoxin, diiodoquin, amebaquin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.362 OOjs UI icon edit-ltr-progressive.svg
KEGG
MeSH Iodoquinol
PubChem CID
UNII
  • InChI=1S/C9H5I2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H X mark.svgN
    Key: UXZFQZANDVDGMM-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C9H5I2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H
    Key: UXZFQZANDVDGMM-UHFFFAOYAF
  • C1=CC2=C(C(=C(C=C2I)I)O)N=C1
Properties
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).
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The quinoline derivative diiodohydroxyquinoline (INN), or iodoquinol (USAN), brand name Diodoquin, 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 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.

Diiodohydroxyquinoline enhances zinc absorption in the zinc deficiency disorder acrodermatitis enteropathica, probably because it acts as a zinc ionophore. [5]

See also

Related Research Articles

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Dientamoeba fragilis is a species of single-celled excavates found in the gastrointestinal tract of some humans, pigs and gorillas. It causes gastrointestinal upset in some people, but not in others. It is an important cause of travellers diarrhoea, chronic diarrhoea, fatigue and, in children, failure to thrive. Despite this, its role as a "commensal, pathobiont, or pathogen" is still debated. D. fragilis is one of the smaller parasites that are able to live in the human intestine. Dientamoeba fragilis cells are able to survive and move in fresh feces but are sensitive to aerobic environments. They dissociate when in contact or placed in saline, tap water or distilled water.

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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.