CHLOROXINE

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H5Cl2NO
Molecular Weight	214.048
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=C1Cl

InChI

InChIKey=WDFKMLRRRCGAKS-UHFFFAOYSA-N

InChI=1S/C9H5Cl2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H

HIDE SMILES / InChI

Molecular Formula	C9H5Cl2NO
Molecular Weight	214.048
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.acs.org/content/acs/en/molecule-of-the-week/archive/c/molecule-of-the-week-chloroxine.html

Chloroxine, a dichloroquinolinol, was first prepared by A. Hebebrand in 1888. It is an antibacterial drug that has been incorporated into shampoos to treat dandruff and seborrheic dermatitis. It has also been used internally as an antidiarrheal and in the lab as an analytical reagent. The drug was withdrawn from the market in the US by unknown reason.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Severe seborrheic dermatitis of the scalp 1 Sources: http://www.drugs.com/pro/capitrol.html	Curative		Approved 8429	CAPITROL Approved Use Unknown Launch Date 1976

C_max

Value	Dose	Co-administered	Analyte	Population
0.713 μg/g EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16910862/	2 μL single, oral dose: 2 μL route of administration: Oral experiment type: SINGLE co-administered:		CHLOROXINE plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
60.72 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16910862/	2 μL single, oral dose: 2 μL route of administration: Oral experiment type: SINGLE co-administered:		CHLOROXINE plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
48.72 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16910862/	2 μL single, oral dose: 2 μL route of administration: Oral experiment type: SINGLE co-administered:		CHLOROXINE plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:59477	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:59477
ChemicalBook	CB8304708	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8304708
MolPort	MolPort-000-510-505	https://www.molport.com/shop/molecule-link/MolPort-000-510-505
Selleck Chemicals	Chloroxine	http://www.selleckchem.com/products/Chloroxine.html
ZINC	ZINC000000001131	http://zinc15.docking.org/substances/ZINC000000001131
eMolecules	537541	https://www.emolecules.com/cgi-bin/more?vid=537541

PubMed

Title	Date	PubMed
Genotoxicity of ochratoxin A and structurally related compounds in Escherichia coli strains: studies on their mode of action.	1991	1820340
Structure-activity studies in E. coli strains on ochratoxin A (OTA) and its analogues implicate a genotoxic free radical and a cytotoxic thiol derivative as reactive metabolites.	1994 May 1	7513790
Solid phase extractive preconcentration of thorium onto 5,7-dichloroquinoline-8-ol modified benzophenone.	2002 Oct 16	18968799
A monooxygenase catalyzes sequential dechlorinations of 2,4,6-trichlorophenol by oxidative and hydrolytic reactions.	2004 Feb 20	14662756
Clioquinol and pyrrolidine dithiocarbamate complex with copper to form proteasome inhibitors and apoptosis inducers in human breast cancer cells.	2005	16280039
Solid phase extraction preconcentration of cobalt and nickel with 5,7-dichloroquinone-8-ol embedded styrene-ethylene glycol dimethacrylate polymer particles and determination by flame atomic absorption spectrometry (FAAS).	2005 Apr 15	18970015
Selective recognition of neodymium (III) using ion imprinted polymer particles.	2005 Jan-Feb	15386615
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Ion imprinted polymer particles for separation of yttrium from selected lanthanides.	2006 Jun	16833087
The evaluation of liposome-water partitioning of 8-hydroxyquinolines and their copper complexes.	2006 Mar 15	16570598
Investigation of the role of chelating ligand in the synthesis of ion-imprinted polymeric resins on the selective enrichment of uranium(VI).	2007 Mar 28	17386782
Differential modulation of Alzheimer's disease amyloid beta-peptide accumulation by diverse classes of metal ligands.	2007 Nov 1	17680773
Synthesis of nano-pore samarium (III)-imprinted polymer for preconcentrative separation of samarium ions from other lanthanide ions via solid phase extraction.	2008 Aug 8	18611461
5,7-Dichloro-quinolin-8-ol.	2009 Apr 25	21583941
N,N-Dicyclo-hexyl-2-(5,7-dichloro-8-quinol-yloxy)acetamide.	2009 Oct 7	21578274
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	23445471

Patents

Sample Use Guides

In Vivo Use Guide

Apply onto the wet scalp, leave on for approximately three minutes, then rinse.

Route of Administration: Topical

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:13:57 GMT 2023` Edited by `admin` on `Fri Dec 15 15:13:57 GMT 2023`
Record UNII	2I8BD50I8B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CHLOROXINE

Official Name

English

5,7-Dichloro-8-quinolinol

Systematic Name

English

CHLOROXINE [USAN]

Common Name

English

Chloroxine [WHO-DD]

Common Name

English

CHLOROXINE [MART.]

Common Name

English

8-QUINOLINOL, 5,7-DICHLORO-

Systematic Name

English

CAPITROL

Brand Name

English

CHLOROXINE [ORANGE BOOK]

Common Name

English

NSC-3904

Code

English

CHLOROXINE [VANDF]

Common Name

English

CHLOROXINE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29708