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 8583	DERMOSCRIBE ICHYBUM Approved Use Unknown
Dermatitis 10 Sources: http://crownlaboratories.com/wp-content/uploads/2015/08/AF_DI.pdf	Primary	Approved 8583	Dermasorb AF Approved Use Unknown
Eczema 46 Sources: http://crownlaboratories.com/wp-content/uploads/2015/08/AF_DI.pdf	Primary	Approved 8583	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 Health Status: unhealthy Age Group: 32 years Sex: M 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 Health Status: unhealthy Age Group: 43 years Sex: F 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 Health Status: unhealthy Age Group: adult Sex: unknown 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 Health Status: unhealthy Age Group: 32 years Sex: M 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 Health Status: unhealthy Age Group: 43 years Sex: F 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 Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/157250/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		P-gp 301

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1932	inducer 1966 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
Aaron Chemicals	AR003NDE	http://www.aaronchem.com/130-26-7
abcr GmbH	AB126750	http://www.abcr.com/shop/en/AB126750
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
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
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
BioSynth	Q-200875	https://www.biosynth.com/en/products/life-science/culture-media-additives/products/Q-200875.html
BLD Pharm	BD103586	http://www.bldpharm.com/products/130-26-7.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
eNovation Chemicals	D617634	https://www.enovationchem.com/ProductDetails.asp?ProductID=D617634
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
iChemical	EBD53345	http://www.ichemical.com/products/130-26-7.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Iodochem	ID10298	https://www.iodochem.com/product/130-26-7
Lab Network	LN00194812	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00194812
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
Matrix Scientific	184515	https://www.matrixscientific.com/184515.html
mcule	MCULE-5389218452	https://mcule.com/MCULE-5389218452/
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	1138201_USP	https://www.sigmaaldrich.com/catalog/product/usp/1138201?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
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
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

PubMed

Title	Date	PubMed
The redox chemistry of the Alzheimer's disease amyloid beta peptide.	2007-08	17433250
Clioquinol attenuates zinc-dependent beta-cell death and the onset of insulitis and hyperglycemia associated with experimental type I diabetes in mice.	2007-06-22	17434477
Stoichiometry and conditional stability constants of Cu(II) or Zn(II) clioquinol complexes; implications for Alzheimer's and Huntington's disease therapy.	2007-05	17382398
Copper and clioquinol treatment in young APP transgenic and wild-type mice: effects on life expectancy, body weight, and metal-ion levels.	2007-04	17211610
Mechanisms of copper ion mediated Huntington's disease progression.	2007-03-28	17396163
Pharmacokinetics and distribution of clioquinol in golden hamsters.	2007-03	17331342
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.	2007-02-15	17308104
The inhalation anesthetic isoflurane induces a vicious cycle of apoptosis and amyloid beta-protein accumulation.	2007-02-07	17287498
The copper chelator, D-penicillamine, does not attenuate MPTP induced dopamine depletion in mice.	2007-02	16736232
Copper-binding compounds as proteasome inhibitors and apoptosis inducers in human cancer.	2007-01-01	17127289
Oral administration of metal chelator ameliorates motor dysfunction after a small hemorrhage near the internal capsule in rat.	2007-01	17061255
Synthesis and anti-HIV properties of new hydroxyquinoline-polyamine conjugates on cells infected by HIV-1 LAV and HIV-1 BaL viral strains.	2006-12-01	17000109
Medical treatment of vulvar squamous cell hyperplasia.	2006-12	17010347
Novel Schiff base copper complexes of quinoline-2 carboxaldehyde as proteasome inhibitors in human prostate cancer cells.	2006-11-30	17125278
Clioquinol, a Cu(II)/Zn(II) chelator, inhibits both ubiquitination and asparagine hydroxylation of hypoxia-inducible factor-1alpha, leading to expression of vascular endothelial growth factor and erythropoietin in normoxic cells.	2006-11-10	16973622
Aluminum and other metals in Alzheimer's disease: a review of potential therapy with chelating agents.	2006-11	17119296
Short G-rich oligonucleotides as a potential therapeutic for Huntington's Disease.	2006-10-02	17014717
Therapeutic treatments for Alzheimer's disease based on metal bioavailability.	2006-10	17160147
Natural distribution of environmental radon daughters in the different brain areas of an Alzheimer disease victim.	2006-09-11	16965619
Iron: a new target for pharmacological intervention in neurodegenerative diseases.	2006-09	17101458
European Standard Series patch test results from a contact dermatitis clinic in Israel during the 7-year period from 1998 to 2004.	2006-08	16930229
Clioquinol and docosahexaenoic acid act synergistically to kill tumor cells.	2006-07	16891473
Degradation of the Alzheimer disease amyloid beta-peptide by metal-dependent up-regulation of metalloprotease activity.	2006-06-30	16648635
1,1'-Xylyl bis-1,4,8,11-tetraaza cyclotetradecane: a new potential copper chelator agent for neuroprotection in Alzheimer's disease. Its comparative effects with clioquinol on rat brain copper distribution.	2006-06-15	16581247
Determination of 5-chloro-7-iodo-8-quinolinol (clioquinol) in plasma and tissues of hamsters by high-performance liquid chromatography and electrochemical detection.	2006-06-06	16714152
Effect of copper and manganese on the de novo generation of protease-resistant prion protein in yeast cells.	2006-05-30	16716078
Metal homeostasis in Alzheimer's disease.	2006-05	16734519
Infiltrative intestinal disease.	2006-04	16627090
Clioquinol treatment in familiar early onset of Alzheimer's disease: Ibach B et al., Pharmacopsychiatry 2005; 38: 178-179.	2006-03	16555171
Radioiodinated clioquinol as a biomarker for beta-amyloid: Zn complexes in Alzheimer's disease.	2006-02	16441845
Clioquinol for the treatment of Alzheimer's Disease.	2006-01-25	16437529
Pharmacological strategies for the prevention of Alzheimer's disease.	2006-01	16370917
A rapid and efficient preparation of [123I]radiopharmaceuticals using a small HPLC (Rocket) column.	2006-01	16129607
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
M30, a novel multifunctional neuroprotective drug with potent iron chelating and brain selective monoamine oxidase-ab inhibitory activity for Parkinson's disease.	2006	17017567
Hope for Huntington's from an old antibiotic.	2005-12	16376812
Translational research on the way to effective therapy for Alzheimer disease.	2005-11	16275806
The oxidative neurotoxicity of clioquinol.	2005-10	15992834
Alzheimer disease beta-amyloid activity mimics cholesterol oxidase.	2005-09	16127459
Evaluation of anti-prionic activity of clioquinol in an in vivo model (Mesocricetus auratus).	2005-08	16244968
[Antimicrobially effective compounded medications. Clinical value and critical comments].	2005-08	15933865
Clioquinol treatment in familiar early onset of Alzheimer's disease: a case report.	2005-07	16025421
Metal ion-dependent effects of clioquinol on the fibril growth of an amyloid {beta} peptide.	2005-04-22	15718230
Anticancer activity of the antibiotic clioquinol.	2005-04-15	15833873
Why nutraceuticals do not prevent or treat Alzheimer's disease.	2005-04-12	15826313
Clioquinol and pyrrolidine dithiocarbamate complex with copper to form proteasome inhibitors and apoptosis inducers in human breast cancer cells.	2005	16280039
Evaluation of phototoxic properties of antimicrobials used in topical preparations by a photohaemolysis test.	2005	15848984
Transient global amnesia after clioquinol: five personal observations from outside Japan.	1979-12	160443
[Subacute myelopathy during a course of treatment with clioquinol in a patient colectomized for Crohn's disease].	1978-01-01	161413

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

IODOCHLORHYDROXYQUIN

Preferred Name

English

CLIOQUINOL

Official Name

English

CLIOQUINOL [VANDF]

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

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