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

Details

Stereochemistry ACHIRAL
Molecular Formula C6H5AsNO6.Na
Molecular Weight 285.0184
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MONOSODIUM 3-NITRO-4-HYDROXYPHENYLARSONATE

SMILES

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

InChI

InChIKey=QWDZBFNAMNUMMZ-UHFFFAOYSA-M
InChI=1S/C6H6AsNO6.Na/c9-6-2-1-4(7(10,11)12)3-5(6)8(13)14;/h1-3,9H,(H2,10,11,12);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C6H5AsNO6
Molecular Weight 262.0286
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including http://news.zoetis.com/press-release/farm-animals/pfizer-suspend-sale-3-nitro-roxarsone-united-states http://www.ncbi.nlm.nih.gov/pubmed/26450128

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
3-Nitro 20

Approved Use

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. 3-Nitro is also approved by the FDA to improve rate of weight gain and feed efficiency in poultry and swine. Its use in swine is negligible.
PubMed

PubMed

TitleDatePubMed
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.
1996 Dec
Patents

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
Created
by admin
on Fri Dec 15 17:42:20 GMT 2023
Edited
by admin
on Fri Dec 15 17:42:20 GMT 2023
Record UNII
0G63Q22980
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MONOSODIUM 3-NITRO-4-HYDROXYPHENYLARSONATE
Systematic Name English
SODIUM 3-NITRO-4-HYDROXYBENZENEARSONATE
Systematic Name English
ARSONIC ACID, (4-HYDROXY-3-NITROPHENYL)-, MONOSODIUM SALT
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C277
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID90975253
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY
CAS
5985-41-1
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY
PUBCHEM
56841614
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY
FDA UNII
0G63Q22980
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY
NCI_THESAURUS
C83972
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY