Roxarsone: Difference between revisions

| verifiedrevid = 444387517

| ImageFileL1 = Roxarsone.png

| ImageFileL1_Ref = {{chemboximage|correct|??}}

| ImageSizeL1 = 121

| ImageAltL1 = Skeletal formula of roxarsone

| ImageFileR1 = Roxarsone-3D-spacefill.png

| ImageSizeR1 = 130

| ImageAltR1 = Space-filling model of the roxarsone molecule

| PIN = (4-Hydroxy-3-nitrophenyl)arsonic acid

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 121-19-7

| PubChem = 5104

| ChemSpiderID = 4925

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 204-453-7

| ChEMBL = 1321154

| UNNumber = 3465

| KEGG = D05771

| KEGG_Ref = {{keggcite|correct|kegg}}

| MeSHName = Roxarsone

| ChEBI_Ref = {{ebicite|correct|EBI}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = H5GU9YQL7L

| RTECS = CY5250000

| Beilstein = 1976533

| Gmelin = 1221211

| SMILES = Oc1ccc(cc1[N+](=O)[O-])[As](O)(O)=O

| SMILES1 = OC1=CC=C(C=C1[N+]([O-])=O)[As](O)(O)=O

| StdInChI = 1S/C6H6AsNO6/c9-6-2-1-4(7(10,11)12)3-5(6)8(13)14/h1-3,9H,(H2,10,11,12)

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| InChI = 1/C6H6AsNO6/c9-6-2-1-4(7(10,11)12)3-5(6)8(13)14/h1-3,9H,(H2,10,11,12)

| StdInChIKey = XMVJITFPVVRMHC-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| InChIKey = XMVJITFPVVRMHC-UHFFFAOYAF

|Section2={{Chembox Properties

| Formula = {{Chem|C|6|AsNH|6|O|6}}

| MolarMass = 263.0365 g mol⁻¹

| MeltingPt = >

| MeltingPtC = 300

|Section3={{Chembox Hazards

| GHSPictograms = {{GHS skull and crossbones}} {{GHS environment}}

| GHSSignalWord = '''DANGER'''

| HPhrases = {{H-phrases|301|331|410}}

| PPhrases = {{P-phrases|261|273|301+310|311|501}}

'''Roxarsone''' is an [[organoarsenic compound]] that has been used in [[poultry production]] as a feed additive to increase weight gain and improve [[feed conversion ratio|feed efficiency]], and as a [[coccidiostat]].<ref name=FDA>{{cite news | author = U.S. Food and Drug Administration | url = https://www.fda.gov/AnimalVeterinary/SafetyHealth/ProductSafetyInformation/ucm258313.htm | title = Questions and Answers Regarding 3-Nitro (Roxarsone) | date = June 8, 2011}}</ref> As of June 2011, it was approved for chicken feed in the [[United States]], [[Canada]], [[Australia]], and 12 other countries.<ref name="NYT2011">{{cite web | last1=Harris | first1=Gardiner | last2=Grady | first2=Denise | title=Pfizer Suspends Sales of Chicken Drug | website=The New York Times | date=9 June 2011 | url=https://www.nytimes.com/2011/06/09/business/09arsenic.html | access-date=19 October 2018}}</ref> The drug was also approved in the United States and elsewhere for use in [[Swine production|pigs]].<ref name=FDA /><ref name="NYT2011"/>

Its use in the United States was voluntarily ended by the manufacturers in June 2011 and has been illegal since 2013.<ref name="withdrawn"/><ref>{{Cite news|url=https://www.chickencheck.in/faq/arsenic-chicken/|title=Arsenic in Chicken: Does chicken meat contain arsenic?|date=21 July 2017|work=Chicken Check In|access-date=20 March 2018|language=en-US}}</ref> Its use was immediately suspended in Malaysia.<ref name="Malaysia">{{cite web | title=Malaysian Pharmaceutical Society | website=Malaysian Pharmaceutical Society | url=http://www.mps.org.my/newsmaster.cfm?&menuid=36&action=view&retrieveid=3448 | access-date=19 October 2018}}</ref> It was banned in Canada in August 2011.<ref name="Canada">{{cite news | title=Sales halted after arsenic found in chicken drug | website=The Globe and Mail | date=3 May 2018 | url=https://www.theglobeandmail.com/life/health-and-fitness/sales-halted-after-arsenic-found-in-chicken-drug/article591962/ | access-date=19 October 2018}}</ref> In Australia, its use in chicken feed was discontinued in 2012.<ref>{{cite web| url=https://www.chicken.org.au/wp-content/uploads/2018/05/New_ACMF_Position-Statement_Roxarsone_180222F-3.pdf| title=Roxarsone not used in the Australian chicken industry| publisher=Australian Meat Chicken Federation| date=24 May 2018| access-date=19 October 2018}}</ref> Roxarsone has been banned in the European Union since 1999.<ref>{{cite web| url=https://www.motherjones.com/tom-philpott/2011/06/arsenic-chicken-fda-roxarsone-pfizer| title=Some Arsenic With That Supermarket Chicken?| first=Tom| last=Philpott| website=Mother Jones| date=11 June 2011| access-date=19 October 2018}}</ref>

==Production and applications==

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]].<ref>GB 226255 19230718</ref> When blended with calcite powder, it is used in poultry feed premixes in some parts of the world. Where available, it can be purchased in 5%, 20% and 50% concentrations.{{cn|date=December 2022}}

Roxarsone was 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.<ref>{{cite news | author = Hileman, B. | url = http://pubs.acs.org/cen/government/85/8515gov2.html | title = Arsenic in Chicken Production | publisher = [[Chemical and Engineering News]] | date = April 9, 2007 | pages = 34–35}}</ref>

==Marketing approval in the United States==

Roxarsone is one of four [[arsenical]] animal drugs that had been approved by the [[U.S. Food and Drug Administration]] (FDA) for use in poultry and swine, along with [[nitarsone]], [[arsanilic acid]], and [[carbarsone]].<ref name=FDA /> 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.<ref name="withdrawn">{{cite news | author = U.S. Food and Drug Administration | url = https://www.fda.gov/AnimalVeterinary/SafetyHealth/ProductSafetyInformation/ucm370568.htm | title = FDA Response to Citizen Petition on Arsenic-based Animal Drugs | date = September 20, 2011}}</ref> In 2015, the FDA withdrew the approval of using nitarsone in animal feeds. The ban came into effect at the end of 2015.<ref name="nitarsone">{{cite news | author = U.S. Food and Drug Administration | url =https://www.fda.gov/AnimalVeterinary/NewsEvents/CVMUpdates/ucm440668.htm | title =FDA Announces Pending Withdrawal of Approval of Nitarsone | date = April 1, 2015}}</ref>

==Controversy==

Roxarsone has attracted attention as a source of [[arsenic]] contamination of poultry and other foods.<ref>{{cite news | author = Institute for Agriculture and Trade Policy | url = http://www.iatp.org/documents/playing-chicken-avoiding-arsenic-in-your-meat | title = Playing Chicken: Avoiding Arsenic in Your Meat | date = April 4, 2006}}</ref><ref>{{cite news | author = Consumer Reports | url = http://www.consumerreports.org/cro/magazine/2012/11/arsenic-in-your-food/index.htm | title = Arsenic in your food | date = November 2012}}</ref> In June 2011, the manufacturers suspended sales of roxarsone in the U.S. and Canada in response to a study by the [[Food and Drug Administration]] (FDA).<ref name=FDA2>{{cite news | author = U.S. Food and Drug Administration | url = https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm258342.htm | title = FDA: Pfizer will voluntarily suspend sale of animal drug 3-Nitro | date = June 8, 2011}}</ref><ref name="AGCanada">{{cite web | author=AGCanada | title=Poultry antibiotic pulled in Canada | website=AGCanada | date=7 July 2011 | url=https://www.agcanada.com/daily/poultry-antibiotic-pulled-in-canada | access-date=19 October 2018}}</ref> The FDA found that roxarsone use was associated with elevated levels of [[inorganic arsenic]] in chicken livers.<ref>{{cite news | author = Cevallos, M. | url = http://www.latimes.com/health/boostershots/la-heb-arsenic-chicken-pfizer-20110608,0,6568583.story | title = Arsenic-containing drug in chicken feed to be pulled from U.S | newspaper = [[LA Times]] | date = June 9, 2011}}</ref> An FDA press release stated that the findings raised "concerns of a very low but completely avoidable exposure to a carcinogen."<ref name=FDA2 />

A 2013 [[market basket]] study conducted in the United States linked the use of roxarsone and other arsenical feed additives to increased levels of inorganic arsenic in [[Poultry#Cuts of poultry|chicken breast meat]], albeit at concentrations well below danger levels set in federal safety standards.<ref>{{cite journal |author1=KE Nachman |author2=PA Baron |author3=G Raber |author4=KA Francesconi |author5=A Navas-Acien |author6=DC Love | title = Roxarsone, Inorganic Arsenic, and Other Arsenic Species in Chicken: A U.S.-Based Market Basket Sample | journal = [[Environmental Health Perspectives]] | year = 2013 | doi = 10.1289/ehp.1206245 |pmid=23694900 |pmc=3701911 | url = http://ehp.niehs.nih.gov/wp-content/uploads/121/5/ehp.1206245.pdf | volume=121 |issue=7 | pages=818–824}}</ref><ref>{{cite news | author = Sabrina Tavernise | url = https://www.nytimes.com/2013/05/11/health/study-finds-an-increase-in-arsenic-levels-in-chicken.html | title = Study Finds an Increase in Arsenic Levels in Chicken | work = New York Times | date = May 11, 2013}}</ref> Breast meat from chickens exposed to arsenical feed additives contained inorganic arsenic at the level of about two parts per billion. Organic chickens not exposed to arsenical feed additives contained about half a part per billion. Federal standards permitted concentrations of 500 parts per billion of total arsenic. The study was performed on chickens raised prior to the voluntary withdrawal of Roxarsone from the market by its manufacturer in June 2011.{{cn|date=December 2022}}

* {{cite journal

|author1=J. R. Garbarino |author2=A. J. Bednar |author3=D. W. Rutherford |author4=R. S. Beyer |author5=R. L. Wershaw |name-list-style=amp | title = Environmental Fate of Roxarsone in Poultry Litter. I. Degradation of Roxarsone during Composting

| journal = Environ. Sci. Technol.

| doi = 10.1021/es026219q

| pmid = 12731831|bibcode=2003EnST...37.1509G }}

* {{cite journal

|author1=Chiou P. W.-S. |author2=Chen K.-L. |author3=Yu B. | title = Effects of roxarsone on performance, toxicity, tissue accumulation and residue of eggs and excreta in laying

| journal = [[Journal of the Science of Food and Agriculture]]

* {{cite conference

|author1=R. L. Wershaw |author2=J. R. Garbarino |author3=M. R. Burkhardt |name-list-style=amp | title = Roxarsone in Natural Water Systems

| conference = Effects of Confined Animal Feeding Operations (CAFOs) on Hydrologic Resources and the Environment

| date = 1999

| location=Fort Collins, Colorado |publisher=U.S. Geological Survey

| url = https://water.usgs.gov/owq/AFO/proceedings/afo/pdf/Wershaw.pdf |accessdate=2020-06-06}}

* {{cite journal

|author1=KB Kerr |author2=JR Narveson |author3=FA Lux | title = Toxicity of an organic arsenical, 3-nitro-4-hydroxyphenylarsonic acid. Residues in chicken tissues

| journal = Journal of Agricultural and Food Chemistry

| volume = 17

| doi =10.1021/jf60166a021

| issue = 6}}

* [https://www.npr.org/blogs/health/2010/11/24/131566322/no-arsenic-in-pardoned-turkeys-but-it-might-be-in-yours No Arsenic In Pardoned Turkeys, But It Might Be In Yours] at [[NPR]]

[[Category:Antiprotozoal agents]]

[[Category:Veterinary drugs]]

[[Category:Food safety]]

[[Category:Medicated feed]]

[[Category:Nitrophenol derivatives]]