U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C8H6N2O2
Molecular Weight 162.1454
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUINDOXIN

SMILES

[O-][N+]1=CC=[N+]([O-])C2=CC=CC=C12

InChI

InChIKey=CKIHZSGJPSDCNC-UHFFFAOYSA-N
InChI=1S/C8H6N2O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H

HIDE SMILES / InChI
Quindoxin (quinoxaline-1,4-dioxide), a former 'growth promoter' used in animal husbandry, has been taken from the market because of its photoallergic properties. Quindoxin increased the live weight gain in young chickens, pigs, and poultry. Quindoxin showed little antibacterial activity in vitro against common gram-positive or gram-negative species under aerobic conditions, but its activity was 10-100 times greater under anaerobic conditions. Under anaerobic conditions, Quindoxin inhibited the growth of Staphylococcus aureus and Escherichia coli. Quindoxin derivatives olaquindox and carbadox have been used as feed additives for growth promotion in pigs, rabbits, and other animals. It is extremely difficult for breeders to avoid exposure to dust containing relatively high concentrations of olaquindox. A very low dose of olaquindox produces contact dermatitis mainly by phototoxic or photoallergic mechanisms.

Approval Year

PubMed

PubMed

TitleDatePubMed
Novel Cu(II) quinoxaline N1,N4-dioxide complexes as selective hypoxic cytotoxins.
2005 May
Reaction kinetics and transformation of carbadox and structurally related compounds with aqueous chlorine.
2006 Dec 1
Novel vanadyl complexes with quinoxaline N(1),N(4)-dioxide derivatives as potent in vitro insulin-mimetic compounds.
2006 Feb
New copper-based complexes with quinoxaline N1,N4-dioxide derivatives, potential antitumoral agents.
2008 Jan
Metabolism of mequindox in liver microsomes of rats, chicken and pigs.
2010 Apr 15
1,2,3,4-Tetra-hydro-phenazine 5,10-dioxide.
2010 Aug 28
Identification of the major metabolites of quinocetone in swine urine using ultra-performance liquid chromatography/electrospray ionization quadrupole time-of-flight tandem mass spectrometry.
2010 Feb
2-Isopropyl-3-methyl-quinoxaline 1,4-dioxide.
2010 Jul 3
Patents

Patents

Name Type Language
QUINDOXIN
INN  
INN  
Official Name English
NSC-21653
Code English
ICI-8173
Code English
ICI 8173
Code English
quindoxin [INN]
Common Name English
NSC-193508
Code English
Classification Tree Code System Code
NCI_THESAURUS C258
Created by admin on Sat Dec 16 17:49:53 GMT 2023 , Edited by admin on Sat Dec 16 17:49:53 GMT 2023
Code System Code Type Description
EVMPD
SUB10208MIG
Created by admin on Sat Dec 16 17:49:53 GMT 2023 , Edited by admin on Sat Dec 16 17:49:53 GMT 2023
PRIMARY
SMS_ID
100000080294
Created by admin on Sat Dec 16 17:49:53 GMT 2023 , Edited by admin on Sat Dec 16 17:49:53 GMT 2023
PRIMARY
PUBCHEM
72073
Created by admin on Sat Dec 16 17:49:53 GMT 2023 , Edited by admin on Sat Dec 16 17:49:53 GMT 2023
PRIMARY
ChEMBL
CHEMBL2104626
Created by admin on Sat Dec 16 17:49:53 GMT 2023 , Edited by admin on Sat Dec 16 17:49:53 GMT 2023
PRIMARY
ECHA (EC/EINECS)
219-352-3
Created by admin on Sat Dec 16 17:49:53 GMT 2023 , Edited by admin on Sat Dec 16 17:49:53 GMT 2023
PRIMARY
FDA UNII
AMX8J6YS1H
Created by admin on Sat Dec 16 17:49:53 GMT 2023 , Edited by admin on Sat Dec 16 17:49:53 GMT 2023
PRIMARY
NCI_THESAURUS
C72588
Created by admin on Sat Dec 16 17:49:53 GMT 2023 , Edited by admin on Sat Dec 16 17:49:53 GMT 2023
PRIMARY
MESH
C003282
Created by admin on Sat Dec 16 17:49:53 GMT 2023 , Edited by admin on Sat Dec 16 17:49:53 GMT 2023
PRIMARY
INN
3145
Created by admin on Sat Dec 16 17:49:53 GMT 2023 , Edited by admin on Sat Dec 16 17:49:53 GMT 2023
PRIMARY
EPA CompTox
DTXSID8046165
Created by admin on Sat Dec 16 17:49:53 GMT 2023 , Edited by admin on Sat Dec 16 17:49:53 GMT 2023
PRIMARY
NSC
21653
Created by admin on Sat Dec 16 17:49:53 GMT 2023 , Edited by admin on Sat Dec 16 17:49:53 GMT 2023
PRIMARY
NSC
193508
Created by admin on Sat Dec 16 17:49:53 GMT 2023 , Edited by admin on Sat Dec 16 17:49:53 GMT 2023
PRIMARY
CAS
2423-66-7
Created by admin on Sat Dec 16 17:49:53 GMT 2023 , Edited by admin on Sat Dec 16 17:49:53 GMT 2023
PRIMARY