CLIOQUINOL

US Approved OTC

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 Search

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

Description
Sources: http://www.nature.com/nm/journal/v15/n4/full/nm0409-356.html
Curator's Comment: Description was created based on several sources, including: https://pubchem.ncbi.nlm.nih.gov/compound/clioquinol; https://www.ebi.ac.uk/chembldb/compound/inspect/CHEMBL497; http://www.cell.com/trends/neurosciences/pdf/S0166-2236(00)02086-5.pdf http://www.ncbi.nlm.nih.gov/pubmed/11598313; http://harvoa.org/polio/smon.htm; http://www.ncbi.nlm.nih.gov/pubmed/20526539

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

Condition	Modality	Highest Phase	Product
Pruritus Ani 1 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=134a88a1-13e5-4da0-8270-c380b57aaeb7	Curative	Approved 8429	DERMOSCRIBE ICHYBUM Approved Use Unknown
Dermatitis 10 Sources: http://crownlaboratories.com/wp-content/uploads/2015/08/AF_DI.pdf	Primary	Approved 8429	Dermasorb AF Approved Use Unknown
Eczema 46 Sources: http://crownlaboratories.com/wp-content/uploads/2015/08/AF_DI.pdf	Primary	Approved 8429	Dermasorb AF Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
42 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22683301/	1600 mg 2 times / day multiple, oral dose: 1600 mg route of administration: Oral experiment type: MULTIPLE co-administered:		CLIOQUINOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
1600 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22683301/	1600 mg 2 times / day multiple, oral dose: 1600 mg route of administration: Oral experiment type: MULTIPLE co-administered:		CLIOQUINOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
41 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22683301/	1600 mg 2 times / day multiple, oral dose: 1600 mg route of administration: Oral experiment type: MULTIPLE co-administered:		CLIOQUINOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
4 g single, oral Studied dose Dose: 4 g Route: oral Route: single Dose: 4 g Sources: https://pubmed.ncbi.nlm.nih.gov/2950208/	unhealthy, 32 years n = 1 Health Status: unhealthy Condition: acute episode of abdominal pain and nausea Age Group: 32 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2950208/	Other AEs: Late onset epilepsy... Other AEs: Late onset epilepsy (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/2950208/
5 g single, oral Studied dose Dose: 5 g Route: oral Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/2950208/	unhealthy, 43 years n = 1 Health Status: unhealthy Condition: intestinal infection Age Group: 43 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2950208/	Other AEs: Late onset epilepsy... Other AEs: Late onset epilepsy (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/2950208/
6 % 1 times / day steady, topical Recommended Dose: 6 %, 1 times / day Route: topical Route: steady Dose: 6 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/157250/	unhealthy, adult n = 1756 Health Status: unhealthy Condition: eczema Age Group: adult Sex: unknown Population Size: 1756 Sources: https://pubmed.ncbi.nlm.nih.gov/157250/	Other AEs: Skin irritation... Other AEs: Skin irritation (35 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/157250/

AEs

AE	Significance	Dose	Population
Late onset epilepsy	1 patient	4 g single, oral Studied dose Dose: 4 g Route: oral Route: single Dose: 4 g Sources: https://pubmed.ncbi.nlm.nih.gov/2950208/	unhealthy, 32 years n = 1 Health Status: unhealthy Condition: acute episode of abdominal pain and nausea Age Group: 32 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2950208/
Late onset epilepsy	1 patient	5 g single, oral Studied dose Dose: 5 g Route: oral Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/2950208/	unhealthy, 43 years n = 1 Health Status: unhealthy Condition: intestinal infection Age Group: 43 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2950208/
Skin irritation	35 patients	6 % 1 times / day steady, topical Recommended Dose: 6 %, 1 times / day Route: topical Route: steady Dose: 6 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/157250/	unhealthy, adult n = 1756 Health Status: unhealthy Condition: eczema Age Group: adult Sex: unknown Population Size: 1756 Sources: https://pubmed.ncbi.nlm.nih.gov/157250/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		P-gp 257

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1650	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/30738852/	no

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0219	http://www.3bsc.com/index/pro_info.php?id=19575
AA Blocks	AA003MLM	https://www.aablocks.com/goods/Goods/detail?id=AA003MLM
AEchem Scientific Corp., USA	AE042367	http://www.aechemsc.com/info_products/AE042367.php
AHH Chemical co.,ltd	API-1205	http://www.ahhchemical.com/product/API-1205.html
AK Scientific, Inc. (AKSCI)	L813	http://www.aksci.com/item_detail.php?cat=L813
AK Scientific, Inc. (AKSCI)	V2416	http://www.aksci.com/item_detail.php?cat=V2416
Aaron Chemicals	AR003NDE	http://www.aaronchem.com/130-26-7
AbMole Bioscience	M5528	http://www.abmole.com/products/clioquinol.html
Acadechem	ACDS-033102	http://www.acadechemical.com/product/107801
Achemica	ACMC-1CD8U	http://www.achemica.com/prodinfo/?id=117868
Achemo Scientific Limited	AC-15595	http://www.achemo.com/search/?Keyword=130-26-7
Achemtek	0104-017864	http://www.achemtek.com/130-26-7
Adooq BioScience	A16461	https://www.adooq.com/clioquinol.html
Alfa Aesar	A11137	https://www.alfa.com/en/catalog/A11137/
Alinda	ALBB-031653	http://alinda.ru/finechem_en_.html?i=ALBB-031653
Anward	ANW-19167	http://www.anward.com/pro_result/19187
Ark Pharm	AK-57345	http://www.arkpharminc.com/products/130-26-7.html
Avantor Inc	101183-410	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101183-410
BLD Pharm	BD103586	http://www.bldpharm.com/products/130-26-7.html
BioSynth	Q-200875	https://www.biosynth.com/en/products/life-science/culture-media-additives/products/Q-200875.html
Calbiochem	233165	http://www.emdbiosciences.com/product/233165
Capot Chemical	16777	http://www.capotchem.com/en/16777.htm
Capot Chemical	PubChem16777	http://www.capotchem.com/en/16777.htm
Chem Scene	CS-4283	http://www.chemscene.com/130-26-7.html
ChemMol	30111781	http://www.chemmol.com/chemmol/30111781.html
ChemMol	49404006	http://www.chemmol.com/chemmol/49404006.html
ChemMol	96700213	http://www.chemmol.com/chemmol/96700213.html
Chemspace	CSSB00000211503	https://chem-space.com/CSSB00000211503
Clearsynth	CS-T-13125	https://www.clearsynth.com/en/CST13125.html
DC Chemicals	DC10242	http://www.dcchemicals.com/product_show-5_Chloro_8_hydroxy_7_iodoquinoline.html
Debye Scientific	DB-041956	http://www.debyesci.com/cas_130-26-7.html
EMD Millipore	233165	http://www.emdbiosciences.com/product/233165
Enamine	Z2768770393	https://www.enaminestore.com/catalog/Z2768770393
Finetech	FT-0603209	http://www.finetechnology-ind.com/prod/detail/pub/130-26-7.html
Glentham Life Sciences	GP1671	http://www.glentham.com/products/product/GP1671/
Hairui	HR136705	http://www.hairuichem.com/en/product/130-26-7.html
Iodochem	ID10298	https://www.iodochem.com/product/130-26-7
LGC Standards	LGCFOR0312.00	https://www.lgcstandards.com/US/en/p/LGCFOR0312.00
LGC Standards	MM0312.00	https://www.lgcstandards.com/US/en/p/MM0312.00
Lab Network	LN00194812	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00194812
Matrix Scientific	184515	https://www.matrixscientific.com/184515.html
MedChem Express	HY-14603	https://www.medchemexpress.com/Clioquinol.html
Oakwood	236842	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=117841&ExtHyperLink=1
Parchem	28568	http://www.parchem.com/chemical-supplier-distributor/Clioquinol-018568.aspx
Selleck Chemicals	S4601	http://www.selleckchem.com/products/5-chloro-8-hydroxy-7-iodoquinoline.html
Sigma-Aldrich	24880_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/24880?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	33931_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/33931?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	BP084_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/bp084?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	Y0000364_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/y0000364?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1138201_USP	https://www.sigmaaldrich.com/catalog/product/usp/1138201?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S017445	http://www.sinfoobiotech.com/product/1020843
Smolecule	S523982	http://www.smolecule.com/products/s523982
TCI (Tokyo Chemical Industry)	C0187	http://www.tcichemicals.com/eshop/en/us/commodity/C0187/index.html
THE BioTek	bt-263843	https://www.thebiotek.com/product/inhibitors/bt-263843
abcr GmbH	AB126750	http://www.abcr.com/shop/en/AB126750
eNovation Chemicals	D617634	https://www.enovationchem.com/ProductDetails.asp?ProductID=D617634
iChemical	EBD53345	http://www.ichemical.com/products/130-26-7.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-5389218452	https://mcule.com/MCULE-5389218452/

PubMed

Title	Date	PubMed
[Subacute myelopathy during a course of treatment with clioquinol in a patient colectomized for Crohn's disease].	1978 Jan-Jun	161413
Transient global amnesia after clioquinol: five personal observations from outside Japan.	1979 Dec	160443
The same chemicals induce different neurotoxicity when administered in high doses for short term or low doses for long term to rats and dogs.	1992 Feb-Apr	1387790
Contact cross-sensitization among quinolines.	2001 Aug	11488685
'...and C is for Clioquinol' - the AbetaCs of Alzheimer's disease.	2002 Mar	11852134
The metallobiology of Alzheimer's disease.	2003 Apr	12689772
Why participate in an Alzheimer's disease clinical trial? Is it of benefit to carers and patients?	2003 Jun	14620073
In vivo model for the evaluation of molecules active towards transmissible spongiform encephalopathies.	2004 Aug	15372984
Evaluation of anti-prionic activity of clioquinol in an in vivo model (Mesocricetus auratus).	2005 Aug	16244968
Clioquinol treatment in familiar early onset of Alzheimer's disease: a case report.	2005 Jul	16025421
Translational research on the way to effective therapy for Alzheimer disease.	2005 Nov	16275806
Alzheimer disease beta-amyloid activity mimics cholesterol oxidase.	2005 Sep	16127459
Metal specificity of an iron-responsive element in Alzheimer's APP mRNA 5'untranslated region, tolerance of SH-SY5Y and H4 neural cells to desferrioxamine, clioquinol, VK-28, and a piperazine chelator.	2006	17447434
[Contact allergy to preservatives contained in cosmetics].	2006	17125030
Synthesis and anti-HIV properties of new hydroxyquinoline-polyamine conjugates on cells infected by HIV-1 LAV and HIV-1 BaL viral strains.	2006 Dec 1	17000109
A rapid and efficient preparation of [123I]radiopharmaceuticals using a small HPLC (Rocket) column.	2006 Jan	16129607
Clioquinol and docosahexaenoic acid act synergistically to kill tumor cells.	2006 Jul	16891473
Degradation of the Alzheimer disease amyloid beta-peptide by metal-dependent up-regulation of metalloprotease activity.	2006 Jun 30	16648635
Clioquinol treatment in familiar early onset of Alzheimer's disease: Ibach B et al., Pharmacopsychiatry 2005; 38: 178-179.	2006 Mar	16555171
Metal homeostasis in Alzheimer's disease.	2006 May	16734519
Novel Schiff base copper complexes of quinoline-2 carboxaldehyde as proteasome inhibitors in human prostate cancer cells.	2006 Nov 30	17125278
Therapeutic treatments for Alzheimer's disease based on metal bioavailability.	2006 Oct	17160147
Iron: a new target for pharmacological intervention in neurodegenerative diseases.	2006 Sep	17101458
The redox chemistry of the Alzheimer's disease amyloid beta peptide.	2007 Aug	17433250
Clioquinol, a therapeutic agent for Alzheimer's disease, has proteasome-inhibitory, androgen receptor-suppressing, apoptosis-inducing, and antitumor activities in human prostate cancer cells and xenografts.	2007 Feb 15	17308104
Copper-binding compounds as proteasome inhibitors and apoptosis inducers in human cancer.	2007 Jan 1	17127289
Clioquinol attenuates zinc-dependent beta-cell death and the onset of insulitis and hyperglycemia associated with experimental type I diabetes in mice.	2007 Jun 22	17434477
Pharmacokinetics and distribution of clioquinol in golden hamsters.	2007 Mar	17331342
Mechanisms of copper ion mediated Huntington's disease progression.	2007 Mar 28	17396163
Stoichiometry and conditional stability constants of Cu(II) or Zn(II) clioquinol complexes; implications for Alzheimer's and Huntington's disease therapy.	2007 May	17382398

Patents

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

Name

Type

Language

CLIOQUINOL

Official Name

English

CLIOQUINOL [VANDF]

Common Name

English

IODOCHLORHYDROXYQUIN

Common Name

English

Clioquinol [WHO-DD]

Common Name

English

NSC-74938

Code

English

CLIOQUINOL [USP-RS]

Common Name

English

CLIOQUINOL [HSDB]

Common Name

English

NSC-3531

Code

English

clioquinol [INN]

Common Name

English

8-QUINOLINOL, 5-CHLORO-7-IODO-

Systematic Name

English

CLIOQUINOL [ORANGE BOOK]

Common Name

English

5-Chloro-7-iodo-8-quinolinol

Systematic Name

English

CLIOQUINOL [MART.]

Common Name

English

CLIOQUINOL COMPONENT OF NYSTAFORM

Common Name

English

IODOCHLORHYDROXYQUIN [GREEN BOOK]

Common Name

English

5-CHLORO-7-IODOQUINOLIN-8-OL

Systematic Name

English

CLIOQUINOL [EP MONOGRAPH]

Common Name

English

CLIOQUINOL [USP MONOGRAPH]

Common Name

English

NYSTAFORM COMPONENT CLIOQUINOL

Common Name

English

IODOCHLORHYDROXYQUINOLONE

Common Name

English

IODOCHLORHYDROXYQUIN [MI]

Common Name

English

Classification Tree Code System Code

WHO-ATC

D09AA10