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Details

Stereochemistry ACHIRAL
Molecular Formula C9H6ClNO
Molecular Weight 179.603
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOXYQUIN

SMILES

OC1=CC=C(Cl)C2=C1N=CC=C2

InChI

InChIKey=CTQMJYWDVABFRZ-UHFFFAOYSA-N
InChI=1S/C9H6ClNO/c10-7-3-4-8(12)9-6(7)2-1-5-11-9/h1-5,12H

HIDE SMILES / InChI
Molecular Formula C9H6ClNO
Molecular Weight 179.603
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/24513205

Cloxyquin has being shown to be a novel activator of the two-pore domain potassium channel TRESK, which is linked to causing migraines and controls the sensitivity of pain nerves in the brain.

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
UNIPROT: Q208C2 (Acyl-CoA-binding protein)
2
Target ID: UNIPROT: Q208C2 (Acyl-CoA-binding protein)
Inhibitor
8297
 0.097 µM [IC50]
Inhibitor
8297
Activator
1430
 3.8 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Preventing
Basic research
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
5 % multiple, topical
Studied dose
Dose: 5 %
Route: topical
Route: multiple
Dose: 5 %
Sources:
https://pubmed.ncbi.nlm.nih.gov/7758311/
unhealthy, 68 years
n = 1
Health Status: unhealthy
Condition: cutaneous mycosis
Age Group: 68 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/7758311/
Other AEs: Contact dermatitis...
Other AEs:
Contact dermatitis
Sources:
https://pubmed.ncbi.nlm.nih.gov/7758311/
AEs

AEs

AESignificanceDosePopulation
Contact dermatitis
5 % multiple, topical
Studied dose
Dose: 5 %
Route: topical
Route: multiple
Dose: 5 %
Sources:
https://pubmed.ncbi.nlm.nih.gov/7758311/
unhealthy, 68 years
n = 1
Health Status: unhealthy
Condition: cutaneous mycosis
Age Group: 68 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/7758311/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY516669
https://www.001chemical.com/chem/130-16-5
3B Scientific (Wuhan) Corp
3B3-035899
http://www.3bsc.com/index/pro_info.php?id=57931
AA Blocks
AA000TRZ
http://www.aablocks.com/goods/Goods/detail?id=AA000TRZ
AHH Chemical co.,ltd
MT-05571
http://www.ahhchemical.com/product/MT-05571.html
AK Scientific, Inc. (AKSCI)
768831
http://www.aksci.com/item_detail.php?cat=768831
Aaron Chemicals
AR000UJR
http://www.aaronchem.com/130-16-5
AbMole Bioscience
M4922
http://www.abmole.com/products/cloxiquine.html
Acadechem
ACDS-018126
http://www.acadechemical.com/product/92825
Accela ChemBio Inc
SY047042
http://www.accelachem.com/cn/search.html?keyword=SY047042&attname=GoodsCode
Achemica
ACMC-209bhm
http://www.achemica.com/prodinfo/?id=121886
Achemo Scientific Limited
AC-25895
http://www.achemo.com/search/?Keyword=130-16-5
Achemtek
0104-004048
http://www.achemtek.com/130-16-5
Acorn PharmaTech
ACN-040468
http://www.acornpharmatech.com/
Acros Organics
AC109300050
https://www.fishersci.com/shop/products/1-chloro-8-hydroxyquinoline-95-acros-organics/AC109300050
Acros Organics
AC109301000
https://www.fishersci.com/shop/products/1-chloro-8-hydroxyquinoline-95-acros-organics/AC109301000
Acros Organics
AC109305000
https://www.fishersci.com/shop/products/1-chloro-8-hydroxyquinoline-95-acros-organics/AC109305000
Adooq BioScience
A16468
https://www.adooq.com/cloxiquine.html
Alfa Aesar
B22856
https://www.alfa.com/en/catalog/B22856/
Alfa Chemistry
ACM130165
https://materials.alfachemic.com/5-chloro-8-quinolinol-cas-130-16-5-item-56250.htm
Allbio Pharm Co., Ltd
AD10799
http://www.allbiopharm.com/product/n/AD10799
Ambinter
Amb1777292
http://www.ambinter.com/reference/1777292
Angene
AGN-PC-00C4OT
http://www.angenechemical.com/productshow/AGN-PC-00C4OT.html
Anward
ANW-19160
http://www.anward.com/pro_result/19188
Ark Pharm
AK-45933
http://www.arkpharminc.com/products/130-16-5.html
Aurora Fine Chemicals LLC
K01.593.028
http://online.aurorafinechemicals.com/info?ID=K01.593.028
Aurum Pharmatech LLC
NE10457
http://www.Aurumpharmatech.com/Product/ProductDetails/NE10457
Avantor Inc
101179-862
https://us.vwr.com/store/catalog/product.jsp?catalog_number=101179-862
Avantor Inc
200042-272
https://us.vwr.com/store/product/7513911/cloxiquina-95
BLD Pharm
BD17969
http://www.bldpharm.com/products/130-16-5.html
BioSynth
W-108352
https://www.biosynth.com/en/products/chemical-intermediates/basic-intermediates/products/W-108352.html
CSNpharm
CSN12522
https://www.csnpharm.com/products/cloxiquine.html
Capot Chemical
21921
http://www.capotchem.com/en/21921.htm
Capot Chemical
PubChem21921
http://www.capotchem.com/en/21921.htm
Chem Scene
CS-4448
http://www.chemscene.com/130-16-5.html
ChemMol
2000137
http://www.chemmol.com/chemmol/2000137.html
ChemMol
30107515
http://www.chemmol.com/chemmol/30107515.html
ChemMol
49405850
http://www.chemmol.com/chemmol/49405850.html
ChemMol
96700214
http://www.chemmol.com/chemmol/96700214.html
Chemenu
CM112436
http://www.chemenu.com/products/CM112436
Chemspace
CSSB00000212186
https://chem-space.com/CSSB00000212186
Clearsynth
CS-O-06307
https://www.clearsynth.com/en/CSO06307.html
Debye Scientific
DB-041946
http://www.debyesci.com/cas_130-16-5.html
Finetech
FT-0620307
http://www.finetechnology-ind.com/prod/detail/pub/130-16-5.html
Glentham Life Sciences
GK7391
http://www.glentham.com/products/product/GK7391/
Hairui
HR126058
http://www.hairuichem.com/en/product/130-16-5.html
LGC Standards
DRE-A11692130AL-100
https://www.lgcstandards.com/US/en/p/DRE-A11692130AL-100
LGC Standards
DRE-C11692130
https://www.lgcstandards.com/US/en/p/DRE-C11692130
LGC Standards
LGCFOR0391.00
https://www.lgcstandards.com/US/en/p/LGCFOR0391.00
LGC Standards
MM0312.01
https://www.lgcstandards.com/US/en/p/MM0312.01
LGC Standards
MM0391.00
https://www.lgcstandards.com/US/en/p/MM0391.00
Lab Network
LN00195665
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00195665
Matrix Scientific
139959
https://www.matrixscientific.com/139959.html
MedChem Express
HY-B0963
https://www.medchemexpress.com/Cloxiquine.html
Molcore
MC516669
https://www.molcore.com/product/130-16-5
MuseChem
I001155
https://www.musechem.com/product/I001155.html
Parchem
37581
http://www.parchem.com/chemical-supplier-distributor/5-Chloro-8-hydroxyquinoline-027581.aspx
Renno Tech
RP24085
http://www.rennotech.com/product_show.asp?id=29740
Selleck Chemicals
S4559
http://www.selleckchem.com/products/cloxiquine.html
Sigma-Aldrich
C47000_ALDRICH
https://www.sigmaaldrich.com/catalog/product/aldrich/c47000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich
C6383_SIGMA
https://www.sigmaaldrich.com/catalog/product/sigma/c6383?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech
S002469
http://www.sinfoobiotech.com/product/1005867
Smolecule
S587933
https://www.smolecule.com/products/s587933
TCI (Tokyo Chemical Industry)
C0645
http://www.tcichemicals.com/eshop/en/us/commodity/C0645/index.html
THE BioTek
bt-288688
https://www.thebiotek.com/product/others/bt-288688
VladaChem
VL279709-100G
https://www.vladachem.com/product.php?products=130-16-5
abcr GmbH
AB132450
http://www.abcr.com/shop/en/AB132450
eNovation Chemicals
D378769
http://www.enovationchem.com/productDetails.asp?productID=D378769
eNovation Chemicals
D663683
https://enovationchem.com/ProductDetails.asp?ProductID=D663683
eNovation Chemicals
D600492
https://www.enovationchem.com/ProductDetails.asp?ProductID=D600492
eNovation Chemicals
D915120
https://www.enovationchem.com/ProductDetails.asp?ProductID=D915120
eNovation Chemicals
Y1040739
https://www.enovationchem.com/ProductDetails.asp?ProductID=Y1040739
iChemical
EBD34547
http://www.ichemical.com/products/130-16-5.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule
MCULE-2202432462
https://mcule.com/MCULE-2202432462/
PubMed

PubMed

TitleDatePubMed
The evaluation of liposome-water partitioning of 8-hydroxyquinolines and their copper complexes.
2006 Mar 15
In vitro activities of cloxyquin (5-chloroquinolin-8-ol) against Mycobacterium tuberculosis.
2007 Mar
Differential modulation of Alzheimer's disease amyloid beta-peptide accumulation by diverse classes of metal ligands.
2007 Nov 1
Outlook on Thailand's genomics and computational biology research and development.
2008 Jul 25
Bis(μ-5-chloro-quinolin-8-olato)-κN,O:O;κO:N,O-bis-[(acetato-κO,O')lead(II)].
2009 Feb 11
5-Chloro-8-hydroxy-quinolinium nitrate.
2009 May 29
Grafting aluminum(III) 8-hydroxyquinoline derivatives on MCM-41 mesoporous silica for tuning of the light emitting color.
2010 Jun 15
Fragment-based discovery of 8-hydroxyquinoline inhibitors of the HIV-1 integrase-lens epithelium-derived growth factor/p75 (IN-LEDGF/p75) interaction.
2013 Mar 28
Patents

Patents

06500842
3
JP2003515526A
462

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Curator's Comment: Growth of the organisms was determined after reincubation at 37°C for 16 to 24 h by visual determination of a color change from blue to pink. The MIC was defined as the lowest concentration which prevented the color change.
The MICs of cloxyquin for 150 clinical isolates of Mycobacterium tuberculosis ranged from 0.062 to 0.25 g/ml. The MIC50 and MIC90 were 0.125 and 0.25 g/ml, respectively.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:15:26 GMT 2023
Edited
by admin
on Fri Dec 15 15:15:26 GMT 2023
Record UNII
BPF36H1G6S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLOXYQUIN
MI   USAN  
USAN  
Official Name English
5-CHLORO-8-HYDROXYQUINOLINE
Systematic Name English
NSC-35083
Code English
8-QUINOLINOL, 5-CHLORO-
Systematic Name English
CLOXYQUIN [USAN]
Common Name English
Cloxiquine [WHO-DD]
Common Name English
CLOXIQUINE
INN   MART.   WHO-DD  
INN  
Official Name English
cloxiquine [INN]
Common Name English
CLOXIQUINE [MART.]
Common Name English
CLOXYQUIN [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C254
Created by admin on Fri Dec 15 15:15:26 GMT 2023 , Edited by admin on Fri Dec 15 15:15:26 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID4045973
Created by admin on Fri Dec 15 15:15:26 GMT 2023 , Edited by admin on Fri Dec 15 15:15:26 GMT 2023
PRIMARY
FDA UNII
BPF36H1G6S
Created by admin on Fri Dec 15 15:15:26 GMT 2023 , Edited by admin on Fri Dec 15 15:15:26 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-978-1
Created by admin on Fri Dec 15 15:15:26 GMT 2023 , Edited by admin on Fri Dec 15 15:15:26 GMT 2023
PRIMARY
NCI_THESAURUS
C61689
Created by admin on Fri Dec 15 15:15:26 GMT 2023 , Edited by admin on Fri Dec 15 15:15:26 GMT 2023
PRIMARY
ChEMBL
CHEMBL225164
Created by admin on Fri Dec 15 15:15:26 GMT 2023 , Edited by admin on Fri Dec 15 15:15:26 GMT 2023
PRIMARY
SMS_ID
100000084038
Created by admin on Fri Dec 15 15:15:26 GMT 2023 , Edited by admin on Fri Dec 15 15:15:26 GMT 2023
PRIMARY
INN
3428
Created by admin on Fri Dec 15 15:15:26 GMT 2023 , Edited by admin on Fri Dec 15 15:15:26 GMT 2023
PRIMARY
CAS
130-16-5
Created by admin on Fri Dec 15 15:15:26 GMT 2023 , Edited by admin on Fri Dec 15 15:15:26 GMT 2023
PRIMARY
EVMPD
SUB06784MIG
Created by admin on Fri Dec 15 15:15:26 GMT 2023 , Edited by admin on Fri Dec 15 15:15:26 GMT 2023
PRIMARY
DRUG CENTRAL
3114
Created by admin on Fri Dec 15 15:15:26 GMT 2023 , Edited by admin on Fri Dec 15 15:15:26 GMT 2023
PRIMARY
PUBCHEM
2817
Created by admin on Fri Dec 15 15:15:26 GMT 2023 , Edited by admin on Fri Dec 15 15:15:26 GMT 2023
PRIMARY
MERCK INDEX
m3675
Created by admin on Fri Dec 15 15:15:26 GMT 2023 , Edited by admin on Fri Dec 15 15:15:26 GMT 2023
PRIMARY Merck Index
NSC
35083
Created by admin on Fri Dec 15 15:15:26 GMT 2023 , Edited by admin on Fri Dec 15 15:15:26 GMT 2023
PRIMARY
Related Record Type Details
Structure of CLOXYQUIN
ACTIVE MOIETY
NIH
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