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4-Hydroxy-3-nitrobenzenearsonic acid

Roxarsone
Skeletal formula of roxarsone
Space-filling model of the roxarsone molecule
Names
IUPAC name
4-Hydroxy-3-nitrobenzenearsonic acid
Systematic IUPAC name
(4-Hydroxy-3-nitrophenyl)arsonic acid
Other names
3-Nitro-4-hydroxyphenyl arsonic acid
2-Nitrophenol-4-arsonic acid
Identifiers
3D model (JSmol)
1976533
ChEBI
ChemSpider
ECHA InfoCard 100.004.049
EC Number 204-453-7
1221211
KEGG
MeSH Roxarsone
PubChem CID
RTECS number CY5250000
UNII
UN number 3465
Properties
C
6
AsNH
6
O
6
Molar mass 263.0365 g mol−1
Melting point > 300 °C (572 °F; 573 K)
Hazards
GHS pictograms The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H301, H331, H410
P261, P273, P301+310, P311, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Roxarsone is an organoarsenic compound that is widely used in poultry production as a feed additive to increase weight gain and improve feed efficiency, and as a coccidiostat. The drug is also approved in the United States for use in pigs. Roxarsone is marketed as 3-Nitro by Zoetis, a former subsidiary of Pfizer now a publicly traded company. In 2006, approximately one million kilograms of roxarsone were produced in the U.S.

Roxarsone is one of four arsenical animal drugs approved by the U.S. Food and Drug Administration (FDA) for use in poultry and/or swine, along with nitarsone, arsanilic acid, and carbarsone. In September 2013, the FDA announced that Zoetis and Fleming Laboratories would voluntarily withdraw current roxarsone, arsanilic acid, and carbarsone approvals, leaving only nitarsone approvals in place. In 2015 FDA withdraw the approval of using nitarsone in animal feeds. The ban came into effect at the end of 2015. Roxarsone is banned in the European Union.

Roxarsone is a derivative of phenylarsonic acid (C6H5As(O)(OH)2). It was first reported in a 1923 British patent that described the nitration and diazotization of arsanilic acid. When blended with calcite powder, it is used in poultry feed premixes and is usually available in 5%, 20% and 50% concentrations.


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