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Revision as of 20:00, 10 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'CASNo').← Previous edit Latest revision as of 22:39, 11 July 2024 edit undoCitation bot (talk | contribs)Bots5,418,802 edits Added date. | Use this bot. Report bugs. | Suggested by Abductive | Category:Antiparasitic agents | #UCB_Category 30/62 
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{{chembox {{chembox
| Verifiedfields = changed | Verifiedfields = changed
⚫ | verifiedrevid = 460017339
⚫ | UNII_Ref = {{fdacite|changed|FDA}}
⚫ | UNII = M2X04R2E2Y
⚫ | verifiedrevid = 399704976
| ImageFile = Carbadox.svg | ImageFile = Carbadox.svg
| ImageSize = | ImageSize =
| IUPACName = methyl (2''E'')-2-hydrazinecarboxylate | IUPACName = Methyl (2''E'')-2-hydrazinecarboxylate
| OtherNames = | OtherNames = Mecadox
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| Abbreviations = | Abbreviations =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10606106 | ChemSpiderID = 10606106
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 13779 | ChEMBL = 13779
| InChIKey = OVGGLBAWFMIPPY-WUXMJOGZBN | InChIKey = OVGGLBAWFMIPPY-WUXMJOGZBN
Line 19: Line 17:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OVGGLBAWFMIPPY-WUXMJOGZSA-N | StdInChIKey = OVGGLBAWFMIPPY-WUXMJOGZSA-N
| CASNo_Ref = {{cascite|correct|??}} | CASNo_Ref = {{cascite|changed|??}}
| CASNo = <!-- blanked - oldvalue: 6804-07-5 --> | CASNo = 6804-07-5
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
⚫ | UNII = M2X04R2E2Y
| EINECS = 229-879-0 | EINECS = 229-879-0
| PubChem = 5353472 | PubChem = 135403805
| SMILES = COC(=O)N\N=C\c2c()c1ccccc12 | SMILES = COC(=O)N\N=C\c2c()c1ccccc12
| 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+ | 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+
Line 28: Line 28:
| MeSHName = | MeSHName =
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = | ChEBI = 94744
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = | KEGG =
}}
| ATCCode_prefix =
⚫ |Section2={{Chembox Properties
| ATCCode_suffix =
| C=11
| ATC_Supplemental =}}
| H=10
⚫ | Section2 = {{Chembox Properties
| N=4
| Formula = C<sub>11</sub>H<sub>10</sub>N<sub>4</sub>O<sub>4</sub>
| O=4
| MolarMass = 262.22 g/mol
| Appearance = Yellow crystals | Appearance = Yellow crystals
| Density = 1.44 g/cm<sup>3</sup> | Density = 1.44 g/cm<sup>3</sup>
| MeltingPt = 239.5 °C | MeltingPtC = 239.5
| Melting_notes = | MeltingPt_notes =
| BoilingPt = | BoilingPt =
| BoilingPt_notes =
| Boiling_notes =
| Solubility = Insoluble | Solubility = Insoluble
| SolubleOther = | SolubleOther =
| Solvent = | Solvent =
| pKa = | pKa =
| pKb = }} | pKb = }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| GHSPictograms = {{GHS02}}{{GHS07}}
| EUClass = F, T
| GHSSignalWord = Warning
| EUIndex =
| HPhrases = {{H-phrases|228|302}}
| MainHazards =
| PPhrases = {{P-phrases|210|240|241|264|270|280|301+312|330|370+378|501}}
⚫ | NFPA-H =
| NFPA-F = | MainHazards =
| NFPA-R = | NFPA-H =
| NFPA-O = | NFPA-F =
⚫ | NFPA-R =
| RSPhrases = ]: {{R45}}, {{R11}}, {{R22}}<br>]: {{S53}}, {{S45}}
| FlashPt = | NFPA-S =
| Autoignition = | FlashPt =
| ExploLimits = | AutoignitionPt =
| ExploLimits =
| PEL = }} | PEL = }}
}} }}
'''Carbadox''' is a drug that combats bacterial infection in swine, particularly swine dysentary. In early 2004 it was banned by the ] as a ] feed additive and for human consumption.<ref>{{cite
| url = http://www.hc-sc.gc.ca/dhp-mps/vet/faq/faq_mrl-lmr-eng.php#a6
| title = Maximum Residue Limits
| publisher = Health Canada
| accessdate = 2010-07-27
}}</ref> The European Union also forbids the use of Carbadox at any level.{{Citation needed|date=January 2010}} It is approved in the ] for use in ] for up to 42 days before slaughter.{{Citation needed|date=January 2010}}
Australia also forbids the use of Carbadox for Food Producing Animals.<ref>{{cite
| url = http://www.apvma.gov.au/registration/not_permitted.php
| title = Substances Not Permitted for use on Food-Producing Animals in Australia
| publisher = Australian Pesticides and Veterinary Medicines Authority
| accessdate = 2010-08-31
}}</ref>


'''Carbadox''' is a ] that combats infection in ], particularly swine ].

==Indications==
Carbadox is indicated for control of swine dysentery (vibrionic dysentery, bloody scours, or hemorrhagic dysentery); control of bacterial swine ] (] or necrotic enteritis caused by '']''); aid in the prevention of migration and establishment of large roundworm ('']'') infections; aid in the prevention of establishment of nodular worm ('']'') infections.<ref name=cfr>{{cite web |title= 21CFR 558.115 |work= Code of Federal Regulations |publisher= FDA |date= 1 Apr 2014 |url= http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=558.115 |access-date= 23 Mar 2015 }}</ref>

==Safety==
In ]s, carbadox has been shown to be carcinogenic{{cn|date=August 2019}} and to induce birth defects.<ref>{{Cite journal | doi = 10.1016/S0378-4274(01)00522-7 | title = Teratogenic assessment of carbadox in rats | journal = Toxicology Letters | volume = 129 | issue = 1–2 | pages = 115–118 | year = 2002 | last1 = Yoshimura | first1 = Haruo | pmid = 11879981 }}</ref> The ]'s Center for Veterinary Medicine has questioned the safety in light of its possible carcinogenicity.<ref>{{Cite web | url = https://www.fda.gov/animal-veterinary/product-safety-information/questions-and-answers-regarding-carbadox | title = Questions and Answers regarding Carbadox | publisher = Food and Drug Administration | date = July 31, 2019 | access-date = August 7, 2019 }}</ref>

==Regulation==

Carbadox is approved in the ] only for use in ] and may not be used within 42 days of slaughter or used in pregnant animals.<ref name=cfr/> In 2016, the United States ] moved to ban its use in pork, citing a potential cancer risk to humans.<ref>{{cite web |first= Maggie |last= Fox |url= https://www.nbcnews.com/health/health-news/fda-moves-ban-cancer-causing-pork-antibiotic-n553101?cid=sm_fb |title= FDA Moves to Ban Cancer-Causing Pork Antibiotic |work= NBC News |date= 8 April 2016 |access-date= 9 Apr 2016}}</ref> However, as of August 2018, FDA had indefinitely stayed its withdrawal of approval and carbadox remains available. <ref>{{cite web |url= https://www.marketwatch.com/press-release/10-k-phibro-animal-health-corp-2018-08-27 |title= 10-K: PHIBRO ANIMAL HEALTH CORP |publisher= MarketWatch |access-date= 3 Jul 2019}}</ref>

In 2004, carbadox was banned by the ] as a ] feed additive and for human consumption.<ref>{{citation |url= http://www.hc-sc.gc.ca/dhp-mps/vet/faq/faq_mrl-lmr-eng.php#a6 |title= Maximum Residue Limits |publisher= Health Canada |access-date= 2010-07-27|date= 2003-05-15 }}</ref>{{failed verification|date=April 2016}} The European Union also forbids the use of carbadox at any level.<ref>{{cite web |last= Ungemach |first= Fritz R. |title= WHO Food Additives Series: 51 CARBADOX (addendum) |work= WHO Food Additives Series |publisher= INCHEM| url= http://www.inchem.org/documents/jecfa/jecmono/v51je05.htm |access-date= 23 Mar 2015 }}</ref> Australia forbids the use of carbadox in food producing animals.<ref>{{citation |url= http://www.apvma.gov.au/registration/not_permitted.php |title= Substances Not Permitted for use on Food-Producing Animals in Australia |publisher= Australian Pesticides and Veterinary Medicines Authority |access-date= 2010-08-31 |archive-url= https://web.archive.org/web/20110222131102/http://www.apvma.gov.au/registration/not_permitted.php |archive-date= 2011-02-22 |url-status= dead }}</ref>


==References== ==References==
{{reflist}} {{reflist}}


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