Carbarsone

Carbarsone
Names
	Preferred IUPAC name Carbarsone
	Systematic IUPAC name [4-(Carbamoylamino)phenyl]arsonic acid
Identifiers
CAS Number	121-59-5 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEMBL	ChEMBL1331366 ;
ChemSpider	8167 ;
ECHA InfoCard	100.004.077
EC Number	204-484-6;
MeSH	Carbarson
PubChem CID	8480;
UNII	8PK70TXE1T ;
CompTox Dashboard (EPA)	DTXSID4020246 ;
	InChI InChI=1S/C7H9AsN2O4/c9-7(11)10-6-3-1-5(2-4-6)8(12,13)14/h1-4H,(H3,9,10,11)(H2,12,13,14) Key: WWXBHTZSYYGCSG-UHFFFAOYSA-N ; InChI=1/C7H9AsN2O4/c9-7(11)10-6-3-1-5(2-4-6)8(12,13)14/h1-4H,(H3,9,10,11)(H2,12,13,14) Key: WWXBHTZSYYGCSG-UHFFFAOYAW;
	SMILES O=C(Nc1ccc(cc1)[As](=O)(O)O)N; NC(=O)NC1=CC=C(C=C1)[As](O)(O)=O;
Properties
Chemical formula	C7H9AsN2O4
Molar mass	260.081 g·mol−1
Pharmacology
Routes of; administration	Oral
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Carbarsone is an organoarsenic compound used as an antiprotozoal drug for treatment of amebiasis and other infections.[1][2][3] It was available for amebiasis in the United States as late as 1991. Thereafter, it remained available as a turkey feed additive for increasing weight gain and controlling histomoniasis (blackhead disease).[4][5]

Carbarsone is one of four arsenical animal drugs approved by the U.S. Food and Drug Administration for use in poultry and/or swine, along with nitarsone, arsanilic acid, and roxarsone.[6] 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.[7] In 2015 FDA withdrew the approval of using nitarsone in animal feeds. The ban came into effect at the end of 2015.[8]

References

SASAKI T, YOKAGAWA M, WYKOFF DE, RITICHIE LS (1956). "Asymptomatic amebiasis; treatment with atabrine in combination with carbarsone or chiniofon". United States Armed Forces medical journal. 7 (3): 363–8. PMID 13299463.
RADKE RA (1955). "Ameboma of the intestine: an analysis of the disease as presented in 78 collected and 41 previously unreported cases". Ann. Intern. Med. 43 (5): 1048–66. doi:10.7326/0003-4819-43-5-1048. PMID 13268997.
HOEKENGA MT (1 July 1951). "A comparison of aureomycin and carbarsone in the treatment of intestinal amebiasis". Am. J. Trop. Med. Hyg. 31 (4): 423–5. PMID 14857246.
McDougald LR (1979). "Efficacy and compatibility of amprolium and carbarsone against Coccidiosis and blackhead in turkeys". Poult. Sci. 58 (1): 76–80. doi:10.3382/ps.0580076. PMID 572970.
Worden AN, Wood EC (1973). "The effect of Carbarsone (33.6 per cent w-v p-ureidobenzene arsonic acid) on bodyweight gain, food conversion and tissue arsenic levels of turkey poults". J. Sci. Food Agric. 24 (1): 35–41. doi:10.1002/jsfa.2740240107. PMID 4696593.
U.S. Food and Drug Administration (June 8, 2011). "Questions and Answers Regarding 3-Nitro (Roxarsone)".
U.S. Food and Drug Administration (September 20, 2011). "FDA Response to Citizen Petition on Arsenic-based Animal Drugs".
U.S. Food and Drug Administration (April 1, 2015). "FDA Announces Pending Withdrawal of Approval of Nitarsone".

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[pmid13299463-1] SASAKI T, YOKAGAWA M, WYKOFF DE, RITICHIE LS (1956). "Asymptomatic amebiasis; treatment with atabrine in combination with carbarsone or chiniofon". United States Armed Forces medical journal. 7 (3): 363–8. PMID 13299463.

[pmid13268997-2] RADKE RA (1955). "Ameboma of the intestine: an analysis of the disease as presented in 78 collected and 41 previously unreported cases". Ann. Intern. Med. 43 (5): 1048–66. doi:10.7326/0003-4819-43-5-1048. PMID 13268997.

[pmid14857246-3] HOEKENGA MT (1 July 1951). "A comparison of aureomycin and carbarsone in the treatment of intestinal amebiasis". Am. J. Trop. Med. Hyg. 31 (4): 423–5. PMID 14857246.

[pmid572970-4] McDougald LR (1979). "Efficacy and compatibility of amprolium and carbarsone against Coccidiosis and blackhead in turkeys". Poult. Sci. 58 (1): 76–80. doi:10.3382/ps.0580076. PMID 572970.

[pmid4696593-5] Worden AN, Wood EC (1973). "The effect of Carbarsone (33.6 per cent w-v p-ureidobenzene arsonic acid) on bodyweight gain, food conversion and tissue arsenic levels of turkey poults". J. Sci. Food Agric. 24 (1): 35–41. doi:10.1002/jsfa.2740240107. PMID 4696593.

[FDA-6] U.S. Food and Drug Administration (June 8, 2011). "Questions and Answers Regarding 3-Nitro (Roxarsone)".

[7] U.S. Food and Drug Administration (September 20, 2011). "FDA Response to Citizen Petition on Arsenic-based Animal Drugs".

[8] U.S. Food and Drug Administration (April 1, 2015). "FDA Announces Pending Withdrawal of Approval of Nitarsone".