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
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
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.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Quinoxaline N,N'-dioxide derivatives and related compounds as growth inhibitors of Trypanosoma cruzi. Structure-activity relationships. | 2004 Jul 16 |
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Novel Cu(II) quinoxaline N1,N4-dioxide complexes as selective hypoxic cytotoxins. | 2005 May |
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Reaction kinetics and transformation of carbadox and structurally related compounds with aqueous chlorine. | 2006 Dec 1 |
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Metabolism of mequindox in liver microsomes of rats, chicken and pigs. | 2010 Apr 15 |
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1,2,3,4-Tetra-hydro-phenazine 5,10-dioxide. | 2010 Aug 28 |
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2-Isopropyl-3-methyl-quinoxaline 1,4-dioxide. | 2010 Jul 3 |
Patents
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C258
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SUB10208MIG
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100000080294
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219-352-3
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AMX8J6YS1H
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C72588
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C003282
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3145
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193508
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2423-66-7
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ACTIVE MOIETY