Carbadox

Carbadox

Names
IUPAC name Methyl (2E)-2-[(1,4-dioxidoquinoxalin-2-yl)methylene]hydrazinecarboxylate
Other names Mecadox
Identifiers
CAS Number	6804-07-5^N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:94744^Y
ChEMBL	ChEMBL13779^Y
ChemSpider	10606106^Y
ECHA InfoCard	100.027.163
EC Number	229-879-0
PubChem CID	135403805
RTECS number	FE2779000
UNII	M2X04R2E2Y^Y
CompTox Dashboard (EPA)	DTXSID6043913
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+^Y Key: OVGGLBAWFMIPPY-WUXMJOGZSA-N^Y 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/cm^3
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). N verify (what is ^YN ?) 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^[citation needed] 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]^[failed verification] 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. "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