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Merck
CN

C6770

Carbadox

Synonym(s):

3-(2-Quinoxalinylmethylene)carbazic acid methyl ester N,N′-dioxide

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About This Item

Empirical Formula (Hill Notation):
C11H10N4O4
CAS Number:
6804-07-5
Molecular Weight:
262.22
NACRES:
NA.85
PubChem Substance ID:
24892894
UNSPSC Code:
41116107
EC Number:
229-879-0
MDL number:
MFCD00057293

Key Documents

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InChI key

OVGGLBAWFMIPPY-WUXMJOGZSA-N

InChI

1S/C11H10N4O4/c1-19-11(16)13-12-6-8-7-14(17)9-4-2-3-5-10(9)15(8)18/h2-7H,1H3,(H,13,16)/b12-6+

SMILES string

COC(=O)N\N=C\c1cn(=O)c2ccccc2n1=O

form

powder

solubility

1 M NaOH: 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

mode of action

DNA synthesis | interferes

storage temp.

2-8°C

Application

Carbadox has been used to suppress aldosterone production, to study the spread of shiga toxin-producing Escherichia coli (STEC) strains, and to compare different antimicrobial activities.

Biochem/physiol Actions

Carbadox is a quinoxaline-di-N-oxide antibiotic that is generally used in feed to swine to prevent dysentery and improve feed efficiency. It inhibits bacteria by intercalation and induction of mutations in bacterial genome.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B - Flam. Sol. 1

Storage Class

4.1B - Flammable solid hazardous materials

wgk

WGK 3

flash_point_f

64.4 °F - closed cup

flash_point_c

18 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
MKCF3297
MKBW5210V
MKBT3688V
SLBG9102V
SLBC0732V

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Qian Chen et al.
Mutation research, 638(1-2), 11-16 (2007-09-28)
Carbadox, a quinoxaline 1,4-dioxide derivative, is a known mutagen with its functional mechanism yet to be well defined. In the present study we used a shuttle vector assay in vitro to uncover the functional details of carbadox-induced mutagenesis in mammalian
Awais Ihsan et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 51, 330-336 (2012-10-16)
Quinoxaline-1,4-dioxides (QdNOs) are the potent heterocyclic N-oxides with interesting biological properties such as antibacterial, anticandida, antitubercular, anticancer and antiprotozoal activities. Here, we tested and compared the mequindox (MEQ) for mutagenic abilities in a battery of different short term tests according
L Beutin et al.
Antimicrobial agents and chemotherapy, 20(3), 336-343 (1981-09-01)
The quinoxaline-di-N-oxides carbadox, olaquindox, and quindoxin, which are potent antibacterial agents, were tested for mutagenicity in the Salmonella microsomal system. They all induced base pair substitutions and frameshift mutations in Salmonella, and occurred independently of the presence of a rat
G Gizzi et al.
Food additives and contaminants, 24(11), 1226-1235 (2007-09-14)
The performance characteristics of an analytical method based on high-performance liquid chromatography (HPLC) for the detection of the banned growth promoters, carbadox and olaquindox, in feedstuff were determined via a collaborative study. The relative standard deviation of repeatability (RSDr) ranged
Antibacterials that are used as growth promoters in animal husbandry can affect the release of Shiga-toxin-2-converting bacteriophages and Shiga toxin 2 from Escherichia coli strains.
Bernd Kohler, Helge Karch, et al.
Microbiology, 5, 1085-1090 (2000)
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