| Revision as of 10:11, 14 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validation|Chem/Drug← Previous edit |
Latest revision as of 09:22, 21 October 2023 edit undoCitation bot (talk | contribs)Bots5,430,467 edits Alter: issn. | Use this bot. Report bugs. | Suggested by Abductive | Category:Quinolinols | #UCB_Category 24/24 |
| (48 intermediate revisions by 33 users not shown) |
| Line 1: |
Line 1: |
|
{{chembox |
|
{{chembox |
|
|
| Verifiedfields = changed |
| ⚫ |
| UNII_Ref = {{fdacite|correct|FDA}} |
|
|
|
| Watchedfields = changed |
| ⚫ |
| UNII = 63W7IE88K8 |
|
|
| verifiedrevid = 437149853 |
|
| verifiedrevid = 444779295 |
|
|ImageFile=Iodoquinol.png |
|
| ImageFile=Iodoquinol.png |
|
|ImageSize=150px |
|
| ImageSize=150px |
|
|
| ImageAlt=Skeletal formula of diiodohydroxyquinoline |
|
|IUPACName=5,7-diiodoquinolin-8-ol |
|
|
|
| ImageFile1=Iodoquinol 3D ball.png |
|
|OtherNames= |
|
|
|
| ImageSize1=160 |
| ⚫ |
|Section1= {{Chembox Identifiers |
|
|
|
| ImageAlt1=Ball-and-stick model of the diiodohydroxyquinoline molecule |
| ⚫ |
| CASNo=83-73-8 |
|
|
|
| PIN=5,7-Diiodoquinolin-8-ol |
| ⚫ |
| PubChem=3728 |
|
|
|
| OtherNames= Diquinol, ], diiodoquin, amebaquin |
|
⚫ |
|Section1={{Chembox Identifiers |
|
|
| CASNo_Ref = {{cascite|correct|??}} |
|
⚫ |
| CASNo=83-73-8 |
|
⚫ |
| PubChem=3728 |
|
|
| ChEBI = 5950 |
|
|
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
|
|
| ChEMBL = 86754 |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG = D00581 |
|
| KEGG = D00581 |
|
⚫ |
| UNII_Ref = {{fdacite|correct|FDA}} |
| ⚫ |
| SMILES=C1=CC2=C(C(=C(C=C2I)I)O)N=C1 |
|
|
⚫ |
| UNII = 63W7IE88K8 |
| ⚫ |
| MeSHName=Iodoquinol |
|
|
⚫ |
| SMILES=C1=CC2=C(C(=C(C=C2I)I)O)N=C1 |
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|
|
| ChemSpiderID = 3597 |
|
|
| InChI = 1/C9H5I2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H |
|
|
| InChIKey = UXZFQZANDVDGMM-UHFFFAOYAF |
|
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChI = 1S/C9H5I2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H |
|
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChIKey = UXZFQZANDVDGMM-UHFFFAOYSA-N |
|
⚫ |
| MeSHName=Iodoquinol |
|
}} |
|
}} |
|
|Section2= {{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| Formula=C<sub>9</sub>H<sub>5</sub>I<sub>2</sub>NO |
|
| Formula=C<sub>9</sub>H<sub>5</sub>I<sub>2</sub>NO |
|
| MolarMass=396.951 |
|
| MolarMass=396.951 |
|
| Appearance= |
|
| Appearance= |
|
| Density= |
|
| Density= |
|
| MeltingPt= |
|
| MeltingPt= |
|
| BoilingPt= |
|
| BoilingPt= |
|
| Solubility= |
|
| Solubility= |
|
}} |
|
}} |
|
|Section3= {{Chembox Hazards |
|
|Section6={{Chembox Pharmacology |
|
|
| ATCCode_prefix = G01 |
| ⚫ |
| MainHazards= |
|
|
|
| ATCCode_suffix = AC01 |
| ⚫ |
| FlashPt= |
|
|
|
}} |
|
| Autoignition= |
|
|
|
|Section7={{Chembox Hazards |
|
⚫ |
| MainHazards= |
|
⚫ |
| FlashPt= |
|
|
| AutoignitionPt = |
|
}} |
|
}} |
|
}} |
|
}} |
|
|
|
|
|
'''Diiodohydroxyquinoline''' (]) or '''iodoquinol''' (]), widely known by the trade name '''Diodoquin''', is a ] derivative which can be used in the treatment of ].<ref name="pmid2493578">{{cite journal |author=Ghaskadbi S, Vaidya VG |title=In vivo antimutagenic effect of ascorbic acid against mutagenicity of the common antiamebic drug diiodohydroxyquinoline |journal=Mutat. Res. |volume=222 |issue=3 |pages=219–22 |year=1989 |month=March |pmid=2493578 |doi= 10.1016/0165-1218(89)90137-7|url=}}</ref> |
|
The ] derivative '''diiodohydroxyquinoline''' (]), or '''iodoquinol''' (]), brand name '''Diodoquin''', can be used in the treatment of ].<ref name="pmid2493578">{{cite journal |vauthors=Ghaskadbi S, Vaidya VG |title=In vivo antimutagenic effect of ascorbic acid against mutagenicity of the common antiamebic drug diiodohydroxyquinoline |journal=Mutat. Res. |volume=222 |issue=3 |pages=219–22 |date=March 1989 |pmid=2493578 |doi= 10.1016/0165-1218(89)90137-7}}</ref> |
|
|
|
|
|
|
It is poorly absorbed from the ] and is used as a luminal amebicide. It acts by ] of ]s essential for metabolism.<ref name="NagataMarriott2012">{{cite journal|last1=Nagata|first1=Noriyuki|last2=Marriott|first2=Deborah|last3=Harkness|first3=John|last4=Ellis|first4=John T.|last5=Stark|first5=Damien|title=Current treatment options for Dientamoeba fragilis infections|journal=International Journal for Parasitology: Drugs and Drug Resistance|volume=2|year=2012|pages=204–215|issn=2211-3207|doi=10.1016/j.ijpddr.2012.08.002|pmc=3862407|pmid=24533282}}</ref> |
|
Iodoquinol is poorly absorbed from the ] and is amebicidal at the site of infection.<ref>http://www.drugs.com/mmx/iodoquinol.html</ref> It acts by chelating ferrous ions essential for metabolism.<ref>http://web.gideononline.com/web/therapy/index.php?type=drugs&code=20130&view=General</ref> |
|
|
|
|
|
|
|
It was discovered by Adco Co. and introduced as ''diiodohydroxyquinoline''.<ref>{{Cite book|url=https://books.google.com/books?id=TIu28TH_iAYC|title=Pharmaceutical Manufacturing Encyclopedia|edition=3rd|last=Publishing|first=William Andrew|date=2013-01-15|publisher=Elsevier Science|isbn=9780080947266|page=1312|language=en}}</ref> |
|
In the United States this medicine is sold under the names '''Diquinol''', '''Yodoquinol''', and '''Yodoxin'''.<ref>http://www.drugs.com/cons/yodoxin.html</ref> Yodoxin is available in 210- and 650-mg oral tablet form.<ref>http://www.walgreens.com/library/finddrug/druginfo.html?particularDrug=Yodoxin&searchChar=Y</ref> |
|
|
|
|
|
|
Susceptibility of '']'' has been measured.<ref name="pmid8067755">{{cite journal |author=Chan FT, Guan MX, Mackenzie AM, Diaz-Mitoma F |title=Susceptibility testing of Dientamoeba fragilis ATCC 30948 with iodoquinol, paromomycin, tetracycline, and metronidazole |journal=Antimicrob. Agents Chemother. |volume=38 |issue=5 |pages=1157–60 |year=1994 |month=May |pmid=8067755 |pmc=188168 |doi= |url=http://aac.asm.org/cgi/pmidlookup?view=long&pmid=8067755}}</ref> |
|
Susceptibility of '']'' has been measured.<ref name="pmid8067755">{{cite journal |vauthors=Chan FT, Guan MX, Mackenzie AM, Diaz-Mitoma F |title=Susceptibility testing of Dientamoeba fragilis ATCC 30948 with iodoquinol, paromomycin, tetracycline, and metronidazole |journal=Antimicrob. Agents Chemother. |volume=38 |issue=5 |pages=1157–60 |date=May 1994 |pmid=8067755 |pmc=188168 |doi= 10.1128/aac.38.5.1157|url=}}</ref> |
|
|
|
|
|
Iodoquinol is an amebicide used against '']'', and it is active against both ] 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 ], probably because it acts as a zinc ].<ref>{{cite journal |last1=Aggett |first1=P.J. |last2=Delves |first2=H.T. |last3=Harries |first3=J.T. |last4=Bangham |first4=A.D. |title=The possible role of Diodoquin as a zinc ionophore in the treatment of acrodermatitis enteropathica |journal=Biochemical and Biophysical Research Communications |date=March 1979 |volume=87 |issue=2 |pages=513–517 |doi=10.1016/0006-291X(79)91825-4|pmid=375935 }}</ref> |
|
|
|
|
|
==See also== |
|
|
* ] |
|
|
|
|
|
==References== |
|
==References== |
| Line 44: |
Line 73: |
|
{{Agents against amoebozoa}} |
|
{{Agents against amoebozoa}} |
|
{{Excavata antiparasitics}} |
|
{{Excavata antiparasitics}} |
| ⚫ |
] |
|
| ⚫ |
] |
|
|
|
|
|
|
⚫ |
] |
|
|
|
|
⚫ |
] |
|
{{biochem-stub}} |
|
|
|
|
|
] |
|