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Details

Stereochemistry ACHIRAL
Molecular Formula C6H7AsNO3.Na
Molecular Weight 239.036
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SODIUM ARSANILATE

SMILES

[Na+].NC1=CC=C(C=C1)[As](O)([O-])=O

InChI

InChIKey=OUFRIWNNMFWZTM-UHFFFAOYSA-M
InChI=1S/C6H8AsNO3.Na/c8-6-3-1-5(2-4-6)7(9,10)11;/h1-4H,8H2,(H2,9,10,11);/q;+1/p-1

HIDE SMILES / InChI
Molecular Formula C6H7AsNO3
Molecular Weight 216.0463
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/20763444 | https://www.ncbi.nlm.nih.gov/pubmed/21772505 | https://www.ncbi.nlm.nih.gov/pubmed/20219092

Arsanilic acid, also known as aminophenyl arsenic acid or aminophenyl arsonic acid, is an organoarsenic compound first reported in 1863 by Antoine Béchamp. Arsanilic acid is a crystalline powder introduced medically in the late 19th century as Atoxyl, its sodium salt was used by injection in the early 20th century as the first organic arsenical drug, but it was soon found prohibitively toxic for human use. Arsanilic acid saw long use as a veterinary feed additive promoting growth and to prevent or treat dysentery in poultry and swine. In 2013, its approval by US government as an animal drug was voluntarily withdrawn by its sponsors. Still sometimes used in laboratories, Arsanilic acid's legacy is principally through its influence on Paul Ehrlich in launching the chemotherapeutic approach to treating infectious diseases of humans.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Atoxyl

Approved Use

African trypanosomiasis
Primary
Approved
8429
Atoxyl

Approved Use

Syphilis
Curative
Withdrawn
Atoxyl

Approved Use

Unknown
Primary
Withdrawn
Atoxyl

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Immunochemical study of antigenic specificity in delayed hypersensitivity. IV. The production of unresponsiveness to delayed hypersensitivity with a single antigenic determinant.
1965 Sep 1
Immunochemical study of antigenic specificity in delayed hypersensitivity. V. Immunization with monovalent low molecular weight conjugates.
1966 Feb 1
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.
1996 Dec
Hippocampal and striatal M(1) -muscarinic acetylcholine receptors are down-regulated following bilateral vestibular loss in rats.
2016 Dec
Short-term galvanic vestibular stimulation promotes functional recovery and neurogenesis in unilaterally labyrinthectomized rats.
2016 Oct 1
The coordination complex structures and hydrogen bonding in the three-dimensional alkaline earth metal salts (Mg, Ca, Sr and Ba) of (4-aminophenyl)arsonic acid.
2017 Jan 1
Effects of bilateral vestibular deafferentation in rat on hippocampal theta response to somatosensory stimulation, acetylcholine release, and cholinergic neurons in the pedunculopontine tegmental nucleus.
2017 Sep
Patents

Patents

20060229441
4
20110053155
10
7799926
4
US2348417
3
US4665100
7

Sample Use Guides

In Vivo Use Guide
Pigs: 161 mg/liter in drinking water for seven days
Route of Administration: Oral
In Vitro Use Guide
In cultures of retina in vitro, addition of 5X10-3 M sodium arsanilate has caused degeneration of the rod cells
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:08:00 GMT 2023
Edited
by admin
on Fri Dec 15 15:08:00 GMT 2023
Record UNII
UC2409302Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SODIUM ARSANILATE
HSDB   MART.   MI  
Common Name English
SODIUM ANILARSONATE
Common Name English
SOAMIN
Brand Name English
Sodium arsanilate [WHO-DD]
Common Name English
SODIUM ARSANILATE [MART.]
Common Name English
SODIUM ARSANILATE [MI]
Common Name English
SODIUM AMINARSONATE
Common Name English
AS-(4-AMINOPHENYL)ARSONIC ACID SODIUM SALT
Common Name English
SODIUM ARSANILATE [HSDB]
Common Name English
Code System Code Type Description
CAS
10361-33-8
Created by admin on Fri Dec 15 15:08:00 GMT 2023 , Edited by admin on Fri Dec 15 15:08:00 GMT 2023
NON-SPECIFIC STOICHIOMETRY
HSDB
5189
Created by admin on Fri Dec 15 15:08:00 GMT 2023 , Edited by admin on Fri Dec 15 15:08:00 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-869-9
Created by admin on Fri Dec 15 15:08:00 GMT 2023 , Edited by admin on Fri Dec 15 15:08:00 GMT 2023
PRIMARY
EPA CompTox
DTXSID2026022
Created by admin on Fri Dec 15 15:08:00 GMT 2023 , Edited by admin on Fri Dec 15 15:08:00 GMT 2023
PRIMARY
FDA UNII
UC2409302Q
Created by admin on Fri Dec 15 15:08:00 GMT 2023 , Edited by admin on Fri Dec 15 15:08:00 GMT 2023
PRIMARY
PUBCHEM
23670523
Created by admin on Fri Dec 15 15:08:00 GMT 2023 , Edited by admin on Fri Dec 15 15:08:00 GMT 2023
PRIMARY
CHEBI
36049
Created by admin on Fri Dec 15 15:08:00 GMT 2023 , Edited by admin on Fri Dec 15 15:08:00 GMT 2023
PRIMARY
CAS
127-85-5
Created by admin on Fri Dec 15 15:08:00 GMT 2023 , Edited by admin on Fri Dec 15 15:08:00 GMT 2023
PRIMARY
Related Record Type Details
Structure of ARSANILIC ACID
PARENT -> SALT/SOLVATE
Structure of SODIUM ARSANILATE TETRAHYDRATE
SOLVATE->ANHYDROUS
NIH
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