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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:
6804-07-5
Molecular Weight:
262.22
EC Number:
229-879-0
MDL number:
MFCD00057293
UNSPSC Code:
41116107
PubChem Substance ID:
24892894
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

H228,H302,H350

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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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
T Hayashi et al.
Antimicrobial agents and chemotherapy, 32(4), 458-461 (1988-04-01)
Sedecamycin (lankacidin A), one of the lankacidin-group antibiotics, showed potent activity against Treponema hyodysenteriae. The MICs of sedecamycin against 79 field isolates of T. hyodysenteriae ranged from 0.78 to 12.5 micrograms/ml, the MIC for 90% of the strains tested (MIC90)
Amisha D Shah et al.
Environmental science & technology, 40(23), 7228-7235 (2006-12-22)
The potential release of carbadox (CDX), a commonly used antibacterial agent in swine husbandry, into water systems is of a concern due to its carcinogenic and genotoxic effects. Until this study, the reactivity of carbadox (possessing quinoxaline N,N'-dioxide and hydrazone
M C Walsh et al.
Journal of animal science, 90(8), 2599-2608 (2012-02-22)
The objective of this study was to evaluate the effects of water-delivered, direct-fed microbials (DFM) or organic acids on intestinal morphology and active nutrient absorption in weanling pigs after deliberate Salmonella infection. Pigs (n = 88) were weaned at 19
Torey Looft et al.
Frontiers in microbiology, 5, 276-276 (2014-06-25)
Antibiotics are used in livestock and poultry production to treat and prevent disease as well as to promote animal growth. Carbadox is an in-feed antibiotic that is widely used in swine production to prevent dysentery and to improve feed efficiency.
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