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Carbadox

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Carbadox
Names
IUPAC name Methyl (2E)-2-hydrazinecarboxylate
Other names Mecadox
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.027.163 Edit this at Wikidata
EC Number
  • 229-879-0
PubChem CID
RTECS number
  • FE2779000
UNII
CompTox Dashboard (EPA)
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+Key: OVGGLBAWFMIPPY-WUXMJOGZSA-N
  • 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()c1ccccc12
Properties
Chemical formula C11H10N4O4
Molar mass 262.225 g·mol
Appearance Yellow crystals
Density 1.44 g/cm
Melting point 239.5 °C (463.1 °F; 512.6 K)
Solubility in water Insoluble
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS07: Exclamation mark
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Safety

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

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. In 2016, the United States Food and Drug Administration moved to ban its use in pork, citing a potential cancer risk to humans. However, as of August 2018, FDA had indefinitely stayed its withdrawal of approval and carbadox remains available.

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

References

  1. ^ "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 (8 April 2016). "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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