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Clioquinol

VETRANAL®, analytical standard

Synonym(s):

5-Chloro-7-iodo-8-quinolinol, 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
Beilstein/REAXYS Number:
153637
EC Number:
204-984-4
MDL number:
MFCD00006787
UNSPSC Code:
41116107
PubChem Substance ID:
329754701
NACRES:
NA.24

grade

analytical standard

Quality Level

100

product line

VETRANAL®

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

forensics and toxicology
pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

Oc1c(I)cc(Cl)c2cccnc12

InChI

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

InChI key

QCDFBFJGMNKBDO-UHFFFAOYSA-N

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General description

Clioquinol is a 8-hydroxyquinoline derivative, which comes under the category of allergens and finds potential applications as an anti-infective agent for diarrhoea. It can be used like a chelator in the treatment of alzheimer′s disease, since it has good affinity towards zinc and copper ions and can easily cross the blood-brain barrier.

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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Legal Information

VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

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_germany

WGK 3

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL6289
BCCH8158
BCBW1927
SZBD238XV
SZBA221XV

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Clioquinol, a drug for Alzheimer's disease specifically interfering with brain metal metabolism: structural characterization of its zinc (II) and copper (II) complexes
Vaira DM, et al
Inorganic Chemistry, 43, 3795-3379 (2004)
Treatment of Alzheimer?s disease with clioquinol
Regland B, et al.
Dementia and Geriatric Cognitive Disorders, 12, 408-414 (2001)
Kouichi Yoshinari et al.
Toxicology letters, 206(2), 229-233 (2011-08-09)
Clioquinol, originally marketed as an oral intestinal amebicide, was widely used for multiple intestinal disorders. Its use as an oral agent was, however, discontinued because of its possible association with subacute myelo-optico-neuropathy or SMON. Meanwhile, its use for neurodegenerative diseases
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
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