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Key Documents

C6770

Sigma-Aldrich

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:
Molecular Weight:
262.22
EC Number:
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.85

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

SMILES string

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

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+

InChI key

OVGGLBAWFMIPPY-WUXMJOGZSA-N

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.

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

64.4 °F - closed cup

Flash Point(C)

18 °C - closed cup


Certificates of Analysis (COA)

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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
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
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
Thaddeus B Stanton et al.
Applied and environmental microbiology, 74(10), 2950-2956 (2008-03-25)
Brachyspira hyodysenteriae is an anaerobic spirochete and the etiologic agent of swine dysentery. The genome of this spirochete contains a mitomycin C-inducible, prophage-like gene transfer agent designated VSH-1. VSH-1 particles package random 7.5-kb fragments of the B. hyodysenteriae genome and

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