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=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
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 |
|---|---|---|
| 1,2,3,4-Tetra-hydro-phenazine 5,10-dioxide. | 2010-08-28 |
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| 2-Isopropyl-3-methyl-quinoxaline 1,4-dioxide. | 2010-07-03 |
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| Metabolism of mequindox in liver microsomes of rats, chicken and pigs. | 2010-04-15 |
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| 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 |
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| New copper-based complexes with quinoxaline N1,N4-dioxide derivatives, potential antitumoral agents. | 2008-01 |
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| A quinoxaline 1,4-di-N-oxide derivative induces DNA oxidative damage not attenuated by vitamin C and E treatment. | 2007-06-30 |
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| Reaction kinetics and transformation of carbadox and structurally related compounds with aqueous chlorine. | 2006-12-01 |
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| Novel vanadyl complexes with quinoxaline N(1),N(4)-dioxide derivatives as potent in vitro insulin-mimetic compounds. | 2006-02 |
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| Novel Cu(II) quinoxaline N1,N4-dioxide complexes as selective hypoxic cytotoxins. | 2005-05 |
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| Quinoxaline N,N'-dioxide derivatives and related compounds as growth inhibitors of Trypanosoma cruzi. Structure-activity relationships. | 2004-07-16 |
Patents
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Preferred Name | English | ||
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Official Name | English | ||
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Code | English | ||
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Code | English | ||
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Code | English |
| 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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72073
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CHEMBL2104626
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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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DTXSID8046165
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21653
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193508
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2423-66-7
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ACTIVE MOIETY