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Details

Stereochemistry ACHIRAL
Molecular Formula C6H8AsNO3
Molecular Weight 217.0542
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARSANILIC ACID

SMILES

NC1=CC=C(C=C1)[As](O)(O)=O

InChI

InChIKey=XKNKHVGWJDPIRJ-UHFFFAOYSA-N
InChI=1S/C6H8AsNO3/c8-6-3-1-5(2-4-6)7(9,10)11/h1-4H,8H2,(H2,9,10,11)

HIDE SMILES / InChI

Molecular Formula C6H8AsNO3
Molecular Weight 217.0542
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

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 In 2013, its approval by US government as an animal drug was voluntarily withdrawn by its sponsors.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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Atoxyl
Primary
Atoxyl
Curative
Atoxyl
Primary
Atoxyl

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Tox targets

PubMed

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
Record UNII
UDX9AKS7GM
Record Status Validated (UNII)
Record Version