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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
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
Angiogenic potential of 3-nitro-4-hydroxy benzene arsonic acid (roxarsone).
2008 Apr
Genome-wide expression analysis of roxarsone-stimulated growth of broiler chickens (Gallus gallus).
2011 Sep
Exocrine pancreatic carcinogenesis and autotaxin expression.
2012
In vitro and ex vivo angiogenic effects of roxarsone on rat endothelial cells.
2013 Nov 25
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 14:58:42 GMT 2023
Edited
by admin
on Fri Dec 15 14:58:42 GMT 2023
Record UNII
H5GU9YQL7L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ROXARSONE
GREEN BOOK   HSDB   INN   MART.   MI   USAN   USP   USP-RS  
USAN   INN  
Official Name English
4-Hydroxy-3-nitrobenzenearsonic acid
Systematic Name English
ROXARSONE [MI]
Common Name English
ROXARSONE [USP MONOGRAPH]
Common Name English
ROXARSONE [MART.]
Common Name English
ROXARSONE [USP-RS]
Common Name English
NSC-2101
Code English
ROXARSONE [GREEN BOOK]
Common Name English
3-NITRO
Brand Name English
roxarsone [INN]
Common Name English
ROXARSONE [HSDB]
Common Name English
ROXARSONE [USP IMPURITY]
Common Name English
ARSONIC ACID, (4-HYDROXY-3-NITROPHENYL)-
Common Name English
ROXARSONE [USAN]
Common Name English
Code System Code Type Description
INN
2226
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
PUBCHEM
5104
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
EVMPD
SUB10395MIG
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
MESH
D012406
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
NSC
2101
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
MERCK INDEX
m9676
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
204-453-7
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
EPA CompTox
DTXSID9020956
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
CAS
121-19-7
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
CHEBI
35817
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
NCI_THESAURUS
C76429
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
RXCUI
1314413
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY RxNorm
HSDB
4296
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
SMS_ID
100000084365
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
FDA UNII
H5GU9YQL7L
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
DRUG BANK
DB11458
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
RS_ITEM_NUM
1606208
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
WIKIPEDIA
ROXARSONE
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY