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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=C1C=CC=C2

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

Molecular Formula C8H6N2O2
Molecular Weight 162.1454
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
1,2,3,4-Tetra-hydro-phenazine 5,10-dioxide.
2010-08-28
2-Isopropyl-3-methyl-quinoxaline 1,4-dioxide.
2010-07-03
Metabolism of mequindox in liver microsomes of rats, chicken and pigs.
2010-04-15
Identification of the major metabolites of quinocetone in swine urine using ultra-performance liquid chromatography/electrospray ionization quadrupole time-of-flight tandem mass spectrometry.
2010-02
New copper-based complexes with quinoxaline N1,N4-dioxide derivatives, potential antitumoral agents.
2008-01
A quinoxaline 1,4-di-N-oxide derivative induces DNA oxidative damage not attenuated by vitamin C and E treatment.
2007-06-30
Reaction kinetics and transformation of carbadox and structurally related compounds with aqueous chlorine.
2006-12-01
Novel vanadyl complexes with quinoxaline N(1),N(4)-dioxide derivatives as potent in vitro insulin-mimetic compounds.
2006-02
Novel Cu(II) quinoxaline N1,N4-dioxide complexes as selective hypoxic cytotoxins.
2005-05
Quinoxaline N,N'-dioxide derivatives and related compounds as growth inhibitors of Trypanosoma cruzi. Structure-activity relationships.
2004-07-16
Patents

Patents

Substance Class Chemical
Created
by admin
on Wed Apr 02 09:34:28 GMT 2025
Edited
by admin
on Wed Apr 02 09:34:28 GMT 2025
Record UNII
AMX8J6YS1H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ICI 8173
Preferred Name English
QUINDOXIN
INN  
INN  
Official Name English
NSC-21653
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 Wed Apr 02 09:34:28 GMT 2025 , Edited by admin on Wed Apr 02 09:34:28 GMT 2025
Code System Code Type Description
EVMPD
SUB10208MIG
Created by admin on Wed Apr 02 09:34:28 GMT 2025 , Edited by admin on Wed Apr 02 09:34:28 GMT 2025
PRIMARY
SMS_ID
100000080294
Created by admin on Wed Apr 02 09:34:28 GMT 2025 , Edited by admin on Wed Apr 02 09:34:28 GMT 2025
PRIMARY
PUBCHEM
72073
Created by admin on Wed Apr 02 09:34:28 GMT 2025 , Edited by admin on Wed Apr 02 09:34:28 GMT 2025
PRIMARY
ChEMBL
CHEMBL2104626
Created by admin on Wed Apr 02 09:34:28 GMT 2025 , Edited by admin on Wed Apr 02 09:34:28 GMT 2025
PRIMARY
ECHA (EC/EINECS)
219-352-3
Created by admin on Wed Apr 02 09:34:28 GMT 2025 , Edited by admin on Wed Apr 02 09:34:28 GMT 2025
PRIMARY
FDA UNII
AMX8J6YS1H
Created by admin on Wed Apr 02 09:34:28 GMT 2025 , Edited by admin on Wed Apr 02 09:34:28 GMT 2025
PRIMARY
NCI_THESAURUS
C72588
Created by admin on Wed Apr 02 09:34:28 GMT 2025 , Edited by admin on Wed Apr 02 09:34:28 GMT 2025
PRIMARY
MESH
C003282
Created by admin on Wed Apr 02 09:34:28 GMT 2025 , Edited by admin on Wed Apr 02 09:34:28 GMT 2025
PRIMARY
INN
3145
Created by admin on Wed Apr 02 09:34:28 GMT 2025 , Edited by admin on Wed Apr 02 09:34:28 GMT 2025
PRIMARY
EPA CompTox
DTXSID8046165
Created by admin on Wed Apr 02 09:34:28 GMT 2025 , Edited by admin on Wed Apr 02 09:34:28 GMT 2025
PRIMARY
NSC
21653
Created by admin on Wed Apr 02 09:34:28 GMT 2025 , Edited by admin on Wed Apr 02 09:34:28 GMT 2025
PRIMARY
NSC
193508
Created by admin on Wed Apr 02 09:34:28 GMT 2025 , Edited by admin on Wed Apr 02 09:34:28 GMT 2025
PRIMARY
CAS
2423-66-7
Created by admin on Wed Apr 02 09:34:28 GMT 2025 , Edited by admin on Wed Apr 02 09:34:28 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY