ARSANILIC ACID

Possibly Marketed Outside US

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 Search

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

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.who.int/trypanosomiasis_african/country/history/en/index6.html | https://www.ncbi.nlm.nih.gov/pubmed/24251577 | https://www.ncbi.nlm.nih.gov/pubmed/920189 | https://www.ncbi.nlm.nih.gov/pubmed/3742372https://www.ncbi.nlm.nih.gov/pubmed/24136205
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 In 2013, its approval by US government as an animal drug was voluntarily withdrawn by its sponsors.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

Targets

Primary Target	Pharmacology	Condition	Potency
Treponema pallidum 3 Target ID: Treponema pallidum Sources: https://www.ncbi.nlm.nih.gov/pubmed/19868094	Inhibitor 8504
Apoptosis 156 Target ID: WP1018 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23848144	Activator 1447

Conditions

Condition	Modality	Highest Phase	Product
Trypanosomiasis 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24251577 https://www.ncbi.nlm.nih.gov/pubmed/16103665	Primary	Approved 8583	Atoxyl Approved Use African trypanosomiasis
Syphilis 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16103665 https://www.wired.com/2009/08/0831chemotherapy-syphilis/	Primary	Approved 8583	Atoxyl Approved Use Syphilis
Trypanosomiasis 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20763444	Curative	Withdrawn	Atoxyl Approved Use Unknown
Syphilis 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21772505	Primary	Withdrawn	Atoxyl Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 BSEP 550 CYP1A2 2153

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/23670523#section=BioAssay-Results Page: 1.0	inconclusive [IC50 13.3142 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/23670523#section=BioAssay-Results Page: 4.0	inconclusive [IC50 38.8447 uM]
BSEP 554	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/23670523#section=BioAssay-Results Page: 4.0	no [IC50 1000 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/23670523#section=BioAssay-Results Page: 50.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/23670523#section=BioAssay-Results Page: 49.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/23670523#section=BioAssay-Results Page: 3.0	yes [IC50 34.6204 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/23670523#section=BioAssay-Results Page: 49.0

PubMed

Title	Date	PubMed
Effects of bilateral vestibular deafferentation in rat on hippocampal theta response to somatosensory stimulation, acetylcholine release, and cholinergic neurons in the pedunculopontine tegmental nucleus.	2017-09	28349227
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.	2017-01-01	28035104
Hippocampal and striatal M1 -muscarinic acetylcholine receptors are down-regulated following bilateral vestibular loss in rats.	2016-12	27569857
Short-term galvanic vestibular stimulation promotes functional recovery and neurogenesis in unilaterally labyrinthectomized rats.	2016-10-01	27444558
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.	1996-12	9039272
Immunochemical study of antigenic specificity in delayed hypersensitivity. V. Immunization with monovalent low molecular weight conjugates.	1966-02-01	5905240
Immunochemical study of antigenic specificity in delayed hypersensitivity. IV. The production of unresponsiveness to delayed hypersensitivity with a single antigenic determinant.	1965-09-01	5839283

Patents

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 `Wed Apr 02 08:42:34 GMT 2025` Edited by `admin` on `Wed Apr 02 08:42:34 GMT 2025`
Record UNII	UDX9AKS7GM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ARSANILIC ACID

Official Name

English

AS 101

Preferred Name

English

ARSANILIC ACID [MI]

Common Name

English

ARSANILIC ACID [MART.]

Common Name

English

Arsanilic acid [WHO-DD]

Common Name

English

ARSANILIC ACID [GREEN BOOK]

Common Name

English

ARSANILIC ACID [USP MONOGRAPH]

Common Name

English

arsanilic acid [INN]

Common Name

English

NSC-2023

Code

English

ARSANILIC ACID [USP-RS]

Common Name

English

ARSANILIC ACID [USP IMPURITY]

Common Name

English

P-AMINOBENZENEARSONIC ACID

Common Name

English

ARSANILIC ACID [HSDB]

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

129005