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Merck
CN

24880

5-Chloro-7-iodo-8-quinolinol

≥95.0% (HPLC)

Synonym(s):

5-Chloro-8-hydroxy-7-iodoquinoline, Clioquinol, Iodochlorhydroxyquin

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About This Item

Empirical Formula (Hill Notation):
C9H5ClINO
CAS Number:
130-26-7
Molecular Weight:
305.50
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57648095
EC Number:
204-984-4
Beilstein/REAXYS Number:
153637
MDL number:
MFCD00006787
Assay:
≥95.0% (HPLC)
Form:
powder

Key Documents

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Product Name

5-Chloro-7-iodo-8-quinolinol, ≥95.0% (HPLC)

InChI key

QCDFBFJGMNKBDO-UHFFFAOYSA-N

InChI

1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H

SMILES string

Oc1c(I)cc(Cl)c2cccnc12

assay

≥95.0% (HPLC)

form

powder

solubility

dioxane: soluble 0.5 g/10 mL, clear, faintly yellow to yellow

functional group

chloro
iodo

Quality Level

200

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Application

5-Chloro-7-iodo-8-quinolinol has been used in analysis of intracellular free zinc ions with the FluoZin-3 probes using fluorescence microscopy.

General description

5-Chloro-7-iodo-8-quinolinol is an antibiotic with metal-binding properties and exhibits anticancer activity in vitro and in vivo. 5-Chloro-7-iodo-8-quinolinol, its glucuronide and sulfate in serum, urine and milk has been quantitated by gas chromatography.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ9965
BCBW9276
BCBT1809
BCBR8937V
BCBN5847V

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A gas chromatographic determination method of 5-chloro-7-iodo-8-quinolinol and its conjugates in biological fluids.
C Chen et al.
Chemical & pharmaceutical bulletin, 24(1), 97-101 (1976-01-01)
A D Schimmer
Current cancer drug targets, 11(3), 325-331 (2011-01-21)
Clioquinol (5-chloro-7-iodo-quinolin-8-ol) was used in the 1950's-1970's as an oral anti-parasitic agent. More recently, studies have demonstrated that Clioquinol displays preclinical efficacy in the treatment of malignancy. Its anti-cancer activity relates, at least in part, to its ability to inhibit
Aaron D Schimmer et al.
Clinical lymphoma, myeloma & leukemia, 12(5), 330-336 (2012-06-12)
Clioquinol is a small-molecule metal ionophore that inhibits the proteasome through a metal-dependent mechanism. Here, we report a phase I study of clioquinol in patients with refractory hematologic malignancies. Neuropathy and abdominal pain were dose-limiting toxicities. Minimal pharmacodynamic effects were
Amy M Ruschak et al.
Journal of the National Cancer Institute, 103(13), 1007-1017 (2011-05-25)
The proteasome is an intracellular enzyme complex that degrades ubiquitin-tagged proteins and thereby regulates protein levels within the cell. Given this important role in maintaining cellular homeostasis, it is perhaps somewhat surprising that proteasome inhibitors have a therapeutic window. Proteasome
Xinliang Mao et al.
Toxicology letters, 182(1-3), 1-6 (2008-09-25)
5-Chloro-7-iodo-quinolin-8-ol (Clioquinol) is a halogenated 8-hydroxyquinoline that was used in 1950-1970s as an oral anti-parasitic agent for the treatment and prevention of intestinal amebiasis. However in the 1970s oral Clioquinol was withdrawn from the market due to reports of neurotoxicity
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