Carbadox
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 540058

CAS#: 6804-07-5

Description: Carbadox is a livestock anitbiotic and growth promoter. It is particularly effective in treating swine dysentery and enteritis. However, its use has been prohibited in the UK following reports of carcinogenicity and mutagenicity.

Chemical Structure

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Carbadox
CAS# 6804-07-5
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 540058
Name: Carbadox
CAS#: 6804-07-5
Chemical Formula: C11H9N4O4
Exact Mass: 261.06
Molecular Weight: 261.210
Elemental Analysis: C, 50.58; H, 3.47; N, 21.45; O, 24.50

Price and Availability

Size Price Availability Quantity
5g USD 350 2 Weeks
10g USD 550 2 Weeks
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Synonym: Carbadoxum; Fortigro; Getroxel; CCRIS-3002; CCRIS 3002; CCRIS3002; GS-6244; GS 6244; GS6244; HSDB-7028; HSDB 7028; HSDB7028;

IUPAC/Chemical Name: Carbazic acid, 3-(2-quinoxalinylmethylene)-, methyl ester, N(sup 1),N(sup 4)-dioxide

InChi Key: NXQFDWYUYAYCEI-NTUHNPAUSA-N

InChi Code: InChI=1S/C11H9N4O4/c1-19-11(16)15(17,18)13-7-8-6-12-9-4-2-3-5-10(9)14-8/h2-7H,1H3/q-1/b13-7+

SMILES Code: O=C(OC)[N+]([O-])([O-])/N=C/C1=NC2=CC=CC=C2N=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Carbadox is a quinoxaline-di-N-oxide antibiotic compound.
In vitro activity: The results of MTT assay demonstrate a dose-dependent decrease in mitochondrial activity in Vero cells at all concentrations of Carbadox. Treatment with Carbadox at the highest concentration of 160 μg/mL results in cell viability down to only 12%. Cells following Carbadox treatment show a dose-dependent increase of the DNA migration (p<0.01). The nuclear division index (NDI) reduces markedly with the increase doses of Carbadox. Reference: Food Chem Toxicol. 2009 Feb;47(2):328-34. https://linkinghub.elsevier.com/retrieve/pii/S0278-6915(08)00653-4
In vivo activity: Alpha diversities (Shannon diversity, Heips evenness, and inverse Simpson indices) of samples from medicated piglets compare to non-medicated piglets are significantly different at 2, 3, and 4 days after continuous Carbadox, but not different in either late Carbadox or at any time during the withdrawal period. Analysis of the community structure of bacteria in animals shows significant differences at days 3 and 4 of early Carbadox treatment ([R=0.32, p=0.015] and [R=0.54, p=0.003], respectively), but not before starting antibiotic treatment (p=0.82). No significant differences in E. coli colony forming units (CFUs) are observed during the Carbadox-treatment period of the study or late in the withdrawal period. E. coli CFUs are significantly different between the medicated and non-medicated groups on day 2 after the withdrawal of Carbadox. Reference: Front Microbiol. 2014 Jun 10;5:276. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/24959163/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 3.6 13.61

Preparing Stock Solutions

The following data is based on the product molecular weight 261.21 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol: 1. Chen Q, Tang S, Jin X, Zou J, Chen K, Zhang T, Xiao X. Investigation of the genotoxicity of quinocetone, carbadox and olaquindox in vitro using Vero cells. Food Chem Toxicol. 2009 Feb;47(2):328-34. doi: 10.1016/j.fct.2008.11.020. Epub 2008 Nov 21. PMID: 19061932.
In vivo protocol: 1. Looft T, Allen HK, Casey TA, Alt DP, Stanton TB. Carbadox has both temporary and lasting effects on the swine gut microbiota. Front Microbiol. 2014 Jun 10;5:276. doi: 10.3389/fmicb.2014.00276. PMID: 24959163; PMCID: PMC4050737.

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1: Segato G, Biancotto G, Agnoletti F, Berto G, Montesissa C, Benetti C. In vivo studies to highlight possible illegal treatments of rabbits with carbadox and olaquindox. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2015;32(12):1976-91. doi: 10.1080/19440049.2015.1086822. Epub 2015 Oct 21. PubMed PMID: 26400201.

2: Souza Dibai WL, de Alkimin Filho JF, da Silva Oliveira FA, Sampaio de Assis DC, Camargos Lara LJ, de Figueiredo TC, de Vasconcelos Cançado S. HPLC-MS/MS method validation for the detection of carbadox and olaquindox in poultry and swine feedingstuffs. Talanta. 2015 Nov 1;144:740-4. doi: 10.1016/j.talanta.2015.07.029. Epub 2015 Jul 11. PubMed PMID: 26452885.

3: Sniegocki T, Gbylik-Sikorska M, Posyniak A, Zmudzki J. Determination of carbadox and olaquindox metabolites in swine muscle by liquid chromatography/mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Jan 1;944:25-9. doi: 10.1016/j.jchromb.2013.09.039. Epub 2013 Nov 9. PubMed PMID: 24291715.

4: Chen WR, Liu C, Boyd SA, Teppen BJ, Li H. Reduction of carbadox mediated by reaction of Mn(III) with oxalic acid. Environ Sci Technol. 2013 Feb 5;47(3):1357-64. doi: 10.1021/es303895w. Epub 2013 Jan 15. PubMed PMID: 23320784.

5: Le T, Zhu L, Yu H. Dual-label quantum dot-based immunoassay for simultaneous determination of Carbadox and Olaquindox metabolites in animal tissues. Food Chem. 2016 May 15;199:70-4. doi: 10.1016/j.foodchem.2015.11.116. Epub 2015 Nov 26. PubMed PMID: 26775945.

6: Liu ZY, Tao YF, Chen DM, Wang X, Yuan ZH. Identification of carbadox metabolites formed by liver microsomes from rats, pigs and chickens using high-performance liquid chromatography combined with hybrid ion trap/time-of-flight mass spectrometry. Rapid Commun Mass Spectrom. 2011 Jan 30;25(2):341-8. doi: 10.1002/rcm.4833. PubMed PMID: 21192029.

7: Yang J, Liu Z, Li M, Qiu X. Hydroxylation of quinocetone and carbadox is mediated by CYP1As in the chicken (Gallus gallus). Comp Biochem Physiol C Toxicol Pharmacol. 2013 Aug;158(2):84-90. doi: 10.1016/j.cbpc.2013.05.008. Epub 2013 May 28. PubMed PMID: 23726999.

8: Liu ZY, Sun ZL. The metabolism of carbadox, olaquindox, mequindox, quinocetone and cyadox: an overview. Med Chem. 2013 Dec;9(8):1017-27. Review. PubMed PMID: 23521002.

9: Wilt HD, Carlson MS. Effect of supplementing zinc oxide and biotin with or without carbadox on nursery pig performance. J Anim Sci. 2009 Oct;87(10):3253-8. doi: 10.2527/jas.2007-0643. Epub 2009 Jul 2. PubMed PMID: 19574566.

10: Merou A, Kaklamanos G, Theodoridis G. Determination of Carbadox and metabolites of Carbadox and Olaquindox in muscle tissue using high performance liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Jan 15;881-882:90-5. doi: 10.1016/j.jchromb.2011.12.007. Epub 2011 Dec 15. PubMed PMID: 22204872.

11: Le T, Xu J, Jia YY, He HQ, Niu XD, Chen Y. Development and validation of an immunochromatographic assay for the rapid detection of quinoxaline-2-carboxylic acid, the major metabolite of carbadox in the edible tissues of pigs. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2012;29(6):925-34. doi: 10.1080/19440049.2012.662703. Epub 2012 Mar 16. PubMed PMID: 22423958.

12: Chen Q, Chen Y, Qi Y, Hao L, Tang S, Xiao X. Characterization of carbadox-induced mutagenesis using a shuttle vector pSP189 in mammalian cells. Mutat Res. 2008 Feb 1;638(1-2):11-6. Epub 2007 Aug 19. PubMed PMID: 17897684.

13: Boison JO, Lee SC, Gedir RG. A determinative and confirmatory method for residues of the metabolites of carbadox and olaquindox in porcine tissues. Anal Chim Acta. 2009 Apr 1;637(1-2):128-34. doi: 10.1016/j.aca.2008.09.016. Epub 2008 Sep 12. PubMed PMID: 19286021.

14: Chen Q, Tang S, Jin X, Zou J, Chen K, Zhang T, Xiao X. Investigation of the genotoxicity of quinocetone, carbadox and olaquindox in vitro using Vero cells. Food Chem Toxicol. 2009 Feb;47(2):328-34. doi: 10.1016/j.fct.2008.11.020. Epub 2008 Nov 21. PubMed PMID: 19061932.

15: Kesiūnaite G, Naujalis E, Padarauskas A. Matrix solid-phase dispersion extraction of carbadox and olaquindox in feed followed by hydrophilic interaction ultra-high-pressure liquid chromatographic analysis. J Chromatogr A. 2008 Oct 31;1209(1-2):83-7. doi: 10.1016/j.chroma.2008.09.025. Epub 2008 Sep 12. PubMed PMID: 18814878.

16: Gizzi G, Vincent U, von Holst C, de Jong J, Genouel C. Validation of an analytical method for the determination of carbadox and olaquindox in feedstuff by liquid chromatography coupled to UV and/or diode array detection. Food Addit Contam. 2007 Nov;24(11):1226-35. PubMed PMID: 17852387.

17: Bearson BL, Allen HK, Brunelle BW, Lee IS, Casjens SR, Stanton TB. The agricultural antibiotic carbadox induces phage-mediated gene transfer in Salmonella. Front Microbiol. 2014 Feb 11;5:52. doi: 10.3389/fmicb.2014.00052. eCollection 2014. PubMed PMID: 24575089; PubMed Central PMCID: PMC3920066.

18: Looft T, Allen HK, Casey TA, Alt DP, Stanton TB. Carbadox has both temporary and lasting effects on the swine gut microbiota. Front Microbiol. 2014 Jun 10;5:276. doi: 10.3389/fmicb.2014.00276. eCollection 2014. PubMed PMID: 24959163; PubMed Central PMCID: PMC4050737.

19: Stanton TB, Humphrey SB, Sharma VK, Zuerner RL. Collateral effects of antibiotics: carbadox and metronidazole induce VSH-1 and facilitate gene transfer among Brachyspira hyodysenteriae strains. Appl Environ Microbiol. 2008 May;74(10):2950-6. doi: 10.1128/AEM.00189-08. Epub 2008 Mar 21. PubMed PMID: 18359835; PubMed Central PMCID: PMC2394957.

20: Shah AD, Kim JH, Huang CH. Reaction kinetics and transformation of carbadox and structurally related compounds with aqueous chlorine. Environ Sci Technol. 2006 Dec 1;40(23):7228-35. PubMed PMID: 17180971.