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Details

Stereochemistry ACHIRAL
Molecular Formula C9H5ClINO
Molecular Weight 305.5
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLIOQUINOL

SMILES

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

InChI

InChIKey=QCDFBFJGMNKBDO-UHFFFAOYSA-N
InChI=1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H

HIDE SMILES / InChI

Molecular Formula C9H5ClINO
Molecular Weight 305.5
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Clioquinol is a broad-spectrum antibacterial with antifungal properties, bacteriostatic. It is used as an antifungal and antiprotozoal topical drug OTC product for treatment of human infections. Previousely was used for wide number of intestinal disorders including lambliasis, shigellosis, balantidiral dysentery and some forms of diarrheas. The physiologic effect of clioquinol is by increased histamine release and cell-mediated immunity. It is a member of a family hydroxyquinolines which inhibit certain enzymes related to DNA replication. It is a copper, iron and zink chelating agent. It is an organic molecule with a quinolinic acid as its apparent core which itself is a neurotransmitter. In large doses it possesses neurotoxicity and may induce neurological disease such as subacute myelo-optic neuropathy by creating copper deficiency that leads to zink excess. SMON (Sub-Acute-Myelo-Optical-Neuropathy) - a polio-like disease began as an epidemic in 1959 in Japan was believed to be a Clioquinol caused. Clioquinol is a standardized chemical allergen. It has been resurrected as a potential treatment for Alzheimer's disease since it perturbs metallo-chemistry of amyloid and clioquinol treatment has been shown to be beneficial in a mouse model of Alzheimer's disease.

CNS Activity

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
DERMOSCRIBE ICHYBUM
Primary
Dermasorb AF
Primary
Dermasorb AF

Cmax

ValueDoseCo-administeredAnalytePopulation
42 μg/mL
1600 mg 2 times / day multiple, oral
CLIOQUINOL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1600 μg × h/mL
1600 mg 2 times / day multiple, oral
CLIOQUINOL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
41 h
1600 mg 2 times / day multiple, oral
CLIOQUINOL plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
Apply a thin layer to the affected area 3 or 4 times daily (3% clioquinol, 0.5% hydrocortisone)
Route of Administration: Topical
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
7BHQ856EJ5
Record Status Validated (UNII)
Record Version