Carbadox

Carbadox
Names
IUPAC name
Methyl (2E)-2-[(1,4-dioxidoquinoxalin-2-yl)methylene]hydrazinecarboxylate
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.027.163
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EC Number
  • 229-879-0
PubChem CID
RTECS number
  • FE2779000
UNII
InChI
  • 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+ checkY
    Key: OVGGLBAWFMIPPY-WUXMJOGZSA-N checkY
  • InChI=1/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+
    Key: OVGGLBAWFMIPPY-WUXMJOGZBN
SMILES
  • COC(=O)N\N=C\c2c[n+]([O-])c1ccccc1[n+]2[O-]
Properties
Chemical formula
 C11H10N4O4
Molar mass 262.225 g·mol−1
Appearance Yellow crystals
Density 1.44 g/cm3
Melting point 239.5 °C (463.1 °F; 512.6 K)
Solubility in water
 Insoluble
Hazards
GHS labelling:
Pictograms
Signal word
 Warning
Hazard statements
 H228, H302
Precautionary statements
 P210, P240, P241, P264, P270, P280, P301+P312, P330, P370+P378, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Carbadox is a veterinary drug that combats infection in swine, particularly swine dysentery.

Indications

Carbadox is indicated for control of swine dysentery (vibrionic dysentery, bloody scours, or hemorrhagic dysentery); control of bacterial swine enteritis (salmonellosis or necrotic enteritis caused by Salmonella enterica); aid in the prevention of migration and establishment of large roundworm (Ascaris suum) infections; aid in the prevention of establishment of nodular worm (Oesophagostomum) infections.[1]

Safety

In animal models, carbadox has been shown to be carcinogenic and to induce birth defects.[2] The Food and Drug Administration's Center for Veterinary Medicine has questioned the safety in light of its possible carcinogenicity.[3]

Regulation

Carbadox is approved in the United States only for use in swine and may not be used within 42 days of slaughter or used in pregnant animals.[1] In 2016, the United States Food and Drug Administration moved to ban its use in pork, citing a potential cancer risk to humans.[4] However, as of August 2018, FDA had indefinitely stayed its withdrawal of approval and carbadox remains available. [5]

In 2004, carbadox was banned by the Canadian government as a livestock feed additive and for human consumption.[6] The European Union also forbids the use of carbadox at any level.[7] Australia forbids the use of carbadox in food producing animals.[8]

References

  1. 1 2 "21CFR 558.115". Code of Federal Regulations. FDA. 1 Apr 2014. Retrieved 23 Mar 2015.
  2. ↑ Yoshimura, Haruo (2002). "Teratogenic assessment of carbadox in rats". Toxicology Letters. 129 (1–2): 115–118. doi:10.1016/S0378-4274(01)00522-7. PMID 11879981.
  3. ↑ "Questions and Answers regarding Carbadox". Food and Drug Administration. July 31, 2019. Retrieved August 7, 2019.
  4. ↑ Fox, Maggie. "FDA Moves to Ban Cancer-Causing Pork Antibiotic". NBC News. Retrieved 9 Apr 2016.
  5. ↑ "10-K: PHIBRO ANIMAL HEALTH CORP". MarketWatch. Retrieved 3 Jul 2019.
  6. ↑ Maximum Residue Limits, Health Canada, 2003-05-15, retrieved 2010-07-27
  7. ↑ Ungemach, Fritz R. "WHO Food Additives Series: 51 CARBADOX (addendum)". WHO Food Additives Series. INCHEM. Retrieved 23 Mar 2015.
  8. ↑ Substances Not Permitted for use on Food-Producing Animals in Australia, Australian Pesticides and Veterinary Medicines Authority, archived from the original on 2011-02-22, retrieved 2010-08-31
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