U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C6H6AsNO6
Molecular Weight 263.0365
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ROXARSONE

SMILES

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

InChI

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

HIDE SMILES / InChI

Molecular Formula C6H6AsNO6
Molecular Weight 263.0365
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

4-Hydroxy-3-nitrobenzenearsonic acid (commonly 3-Nitro, or its generic, Roxarsone) was a FDA approved for increased rate of weight gain, improved feed efficiency, and improved pigmentation for growing chickens and growing turkeys. For increased rate of weight gain and improved feed efficiency for growing-finishing swine. Roxarsone is marketed as 3-Nitro by Zoetis, a former subsidiary of Pfizer now a publicly traded company. 3-Nitro is indicated for combination use with certain other medications as an effective aid in the prevention of coccidiosis, the most common infection in poultry. Roxarsone promotes angiogenesis in vivo, and a VEGF/VEGFR mechanism may be involved. 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 will came into effect at the end of 2015. Roxarsone is banned in the European Union.

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
3-Nitro 20

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
for animals:in the feed For increased rate of weight gain and improved feed efficiency for growing-finishing swine: Mix 4 ounces (113.4 grams) to 6 ounces (170.1 grams) of 3-Nitro 20 (roxarsone) in 2,000 pounds (909 kg) of a complete feed. Give continuously through the growing-finishing period. As an aid in the treatment of swine dysentery (hemorrhagic enteritis or bloody scours): Mix 2 pounds (909 grams) of 3-Nitro 20 in 2,000 pounds (909 kg) of a complete feed. Give for no more than 6 consecutive days.
Route of Administration: Oral
In Vitro Use Guide
The ability of roxarsone to promote angiogenesis of rat endothelial cells in vitro and from rat aorta rings ex vivo was studied. Endothelial cells from rats were exposed to 0.01-10.00μM roxarsone, 5ng/mL vascular endothelial growth factor (VEGF) as a positive control or phosphate buffer saline (PBS) as a negative control.
Substance Class Chemical
Record UNII
H5GU9YQL7L
Record Status Validated (UNII)
Record Version