Carbadox

Structural formula
General
Surname	Carbadox
other names	Methyl 3- (quinoxalin-2-ylmethylene) carbazate 1,4-dioxide; 2- (methoxycarbonylhydrazonomethyl) quinoxaline 1,4-dioxide;
Molecular formula	C 11 H 10 N 4 O 4
Brief description	yellow solid
External identifiers / databases
EC number	229-879-0
ECHA InfoCard	100.027.163
PubChem	135511839
Wikidata	Q1810456
properties
Molar mass	262.23 g mol −1
Physical state	firmly
Melting point	239.5-240 ° C
Vapor pressure	<0.001 Pa (25 ° C)
solubility	practically insoluble in water
safety instructions
H and P phrases	H: 228-302-350
	P: 201-210-308 + 313
Toxicological data	850 mg kg −1 ( LD 50 , oral , rat )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Carbadox is a chemical compound from the group of carbamates and quinoxaline derivatives .

Extraction and presentation

Carbadox can be obtained from derivatives of quinoxaline 1,4-dioxide ( quindoxine ).

properties

Carbadox is a yellow solid that is practically insoluble in water.

use

Carbadox is a growth-promoting and antibacterial aid that is added to pig feed at a dose of 50 ppm. In many countries around the world it is used for human consumption in animals up to four months old with a four week waiting period before slaughter. Carbadox has not yet been evaluated by the Joint FAO / WHO Expert Committee on Food Additives. In the EU and Switzerland, the use of the compound has been banned since September 1999 because of its carcinogenic effect. In the USA, a ban has been announced by the FDA since April 2016. The antibacterial effect of the compound, discovered in 1964, is based on the inhibition of the DNA synthesis of the bacteria.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on Carbadox in the GESTIS substance database of the IFA , accessed on December 29, 2019(JavaScript required) .
↑ ^a ^b ^c ^d International Chemical Safety Card (ICSC) for Carbadox at the National Institute for Occupational Safety and Health (NIOSH), accessed on October 16, 2016.
↑ Entry on Carbadox in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 29, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ John P. Dirlam, Joseph E. Presslitz, BJ Williams: Synthesis and antibacterial activity of some 3 - [(alkylthio) methyl] quinoxaline 1-oxide derivatives. In: Journal of Medicinal Chemistry. 26, 1983, p. 1122, doi : 10.1021 / jm00362a007 .
^ Joint FAO / WHO Expert Committee on Food Additives (JECFA), Monograph for Carbadox , accessed October 16, 2016.
^ Robert Paul Hunter, Carlos F. Amábile-Cuevas, Jun Lin, Joshua D. Nosanchuk, Rustam Aminov: Low-dose antibiotics: current status and outlook for the future . Frontiers E-books, 2014, ISBN 2-88919-355-1 , pp. 98 ( limited preview in Google Book search).
^ TS Stahly, Department of Animal Science: Growth Response to Carbadox in Pigs with a High or Low Genetic Capacity for Lean Tissue Growth , accessed October 16, 2016.
↑ vetpharm.uzh.ch: CPT: CliniPharm / CliniTox , accessed on October 16, 2016.
↑ fda.gov: Press Announcements> FDA takes steps to withdraw approval of the swine drug carbadox due to safety concerns , accessed October 16, 2016
^ Steeve Giguère, John F. Prescott, Patricia M. Dowling: Antimicrobial Therapy in Veterinary Medicine . John Wiley & Sons, 2013, ISBN 978-1-118-67507-6 ( limited preview in Google Book Search).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on Carbadox in the GESTIS substance database of the IFA , accessed on December 29, 2019(JavaScript required) .

[ICSC-2] International Chemical Safety Card (ICSC) for Carbadox at the National Institute for Occupational Safety and Health (NIOSH), accessed on October 16, 2016.

[CLP_100.027.163-3] Entry on Carbadox in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 29, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .

[DOI10.1021/jm00362a007-4] John P. Dirlam, Joseph E. Presslitz, BJ Williams: Synthesis and antibacterial activity of some 3 - [(alkylthio) methyl] quinoxaline 1-oxide derivatives. In: Journal of Medicinal Chemistry. 26, 1983, p. 1122, doi : 10.1021 / jm00362a007 .

[INCHEM-5] Joint FAO / WHO Expert Committee on Food Additives (JECFA), Monograph for Carbadox , accessed October 16, 2016.

[Robert_Paul_Hunter,_Carlos_F._Amábile-Cuevas,_Jun_Lin,_Joshua_D._Nosanchuk,_Rustam_Aminov-6] Robert Paul Hunter, Carlos F. Amábile-Cuevas, Jun Lin, Joshua D. Nosanchuk, Rustam Aminov: Low-dose antibiotics: current status and outlook for the future . Frontiers E-books, 2014, ISBN 2-88919-355-1 , pp. 98 ( limited preview in Google Book search).

[extension.iastate.edu-7] TS Stahly, Department of Animal Science: Growth Response to Carbadox in Pigs with a High or Low Genetic Capacity for Lean Tissue Growth , accessed October 16, 2016.

[vetpharm.uzh.ch-8] vetpharm.uzh.ch: CPT: CliniPharm / CliniTox , accessed on October 16, 2016.

[fda.gov-9] .gov: Press Announcements> FDA takes steps to withdraw approval of the swine drug carbadox due to safety concerns , accessed October 16, 2016

[Steeve_Giguère,_John_F._Prescott,_Patricia_M._Dowling-10] Steeve Giguère, John F. Prescott, Patricia M. Dowling: Antimicrobial Therapy in Veterinary Medicine . John Wiley & Sons, 2013, ISBN 978-1-118-67507-6 ( limited preview in Google Book Search).