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Details

Stereochemistry ACHIRAL
Molecular Formula C9H5I2NO
Molecular Weight 396.951
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IODOQUINOL

SMILES

OC1=C2N=CC=CC2=C(I)C=C1I

InChI

InChIKey=UXZFQZANDVDGMM-UHFFFAOYSA-N
InChI=1S/C9H5I2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://en.wikipedia.org/wiki/Diiodohydroxyquinoline

The quinoline derivative diiodohydroxyquinoline (INN) or iodoquinol (USAN), one of the halogenated 8-quinolinols widely used as an intestinal antiseptic, especially as an antiamebic agent. Iodoquinol is also used topically in other infections and may cause CNS and eye damage. It was discovered by Adco Co. and introduced as diiodohydroxyquinoline. The mechanism of action is unknown. Iodoquinol acts against the trophozoites of Entamoeba histolytica. Iodoquinol produces its amebicidal effect at the site of infection, since it is poorly absorbed from the gastrointestinal tract and can reach high concentrations in the intestinal lumen.

Originator

Stenhouse, J.|Groves, C.E.
1
Sources: Journal of the Chemical Society, Transactions (1878), 33, 415-422

Approval Year

1953
193
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Withdrawn
Yodoxin

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.
2013-09-05
Differential modulation of Alzheimer's disease amyloid beta-peptide accumulation by diverse classes of metal ligands.
2007-11-01
Acrodermatitis enteropathica-like eruption associated with combined nutritional deficiency.
2005-10
Adverse effects of the antimalaria drug, mefloquine: due to primary liver damage with secondary thyroid involvement?
2002-03-25
Spectrofluorometric determination of erbium in seawater with 5,7-diiodoquinoline-8-ol and rhodamine 6G.
2001-11
The therapeutic effect of 16 antimicrobial agents on Cryptosporidium infection in mice.
1982-04
Chloroquine seizures. Report of four cases.
1968-06-03

Sample Use Guides

In Vivo Use Guide
3 times/day after food
Route of Administration: Oral
In Vitro Use Guide
Iodoquinol 1% produced the broadest and greatest antimicrobial activity as measured by a 3-log reduction of colony-forming units active against all microbes tested following incubation times of 1 or 5 minutes, except M luteus
Name Type Language
IODOQUINOL
HSDB   MI   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
DIIODOHYDROXYQUINOLINE
INN   MART.   WHO-DD  
INN  
Preferred Name English
IODOQUINOL [USP MONOGRAPH]
Common Name English
DIIODOHYDROXYQUINOLINE [MART.]
Common Name English
LANODOXIN
Brand Name English
ENTERODIAMOEBINE
Brand Name English
Diiodohydroxyquinoline [WHO-DD]
Common Name English
IODOQUINOL [HSDB]
Common Name English
ZOAQUIN
Brand Name English
YODOXIN
Brand Name English
DI-IODOHYDROXY QUINOLINE
Systematic Name English
DIODOQUIN
Common Name English
5,7-DIIODO-8-QUINOLINOL
Systematic Name English
IODOQUINOL [USP IMPURITY]
Common Name English
SEARLEQUIN
Brand Name English
NSC-8704
Code English
IODOQUINOL [USP-RS]
Common Name English
diiodohydroxyquinoline [INN]
Common Name English
8-QUINOLINOL, 5,7-DIIODO-
Systematic Name English
IOQUIN
Brand Name English
SS-578
Code English
QUINADOME
Brand Name English
IODOQUINOL [MI]
Common Name English
IODOQUINOL [USAN]
Common Name English
Classification Tree Code System Code
WHO-ATC G01AC01
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LIVERTOX 511
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WHO-VATC QG01AC01
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EPA PESTICIDE CODE 24003
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Code System Code Type Description
FDA UNII
63W7IE88K8
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PRIMARY
INN
1613
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PRIMARY
DRUG CENTRAL
1457
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PRIMARY
PUBCHEM
3728
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PRIMARY
HSDB
3224
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PRIMARY
RXCUI
3435
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PRIMARY RxNorm
SMS_ID
100000082627
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PRIMARY
NSC
8704
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PRIMARY
MESH
D004103
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PRIMARY
MERCK INDEX
m6355
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PRIMARY Merck Index
DAILYMED
63W7IE88K8
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PRIMARY
WIKIPEDIA
DIIODOHYDROXYQUINOLINE
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PRIMARY
CAS
83-73-8
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PRIMARY
CHEBI
5950
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PRIMARY
EVMPD
SUB07142MIG
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PRIMARY
RS_ITEM_NUM
1344509
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PRIMARY
EPA CompTox
DTXSID6023155
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PRIMARY
ChEMBL
CHEMBL86754
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PRIMARY
NCI_THESAURUS
C76008
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PRIMARY
ECHA (EC/EINECS)
201-497-9
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PRIMARY
DRUG BANK
DB09115
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PRIMARY
ACTIVE MOIETY
Structure of IODOQUINOL
NIH
NCATS
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