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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
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 In 2013, its approval by US government as an animal drug was voluntarily withdrawn by its sponsors.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Withdrawn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Withdrawn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
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
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 Sat Dec 16 17:02:00 UTC 2023
Edited
by admin
on Sat Dec 16 17:02:00 UTC 2023
Record UNII
UDX9AKS7GM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARSANILIC ACID
GREEN BOOK   HSDB   INN   MART.   MI   USP   USP-RS   WHO-DD  
INN  
Official 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
AS 101
Code English
ARSANILIC ACID [HSDB]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 129005
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
NCI_THESAURUS C254
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
Code System Code Type Description
RS_ITEM_NUM
1042703
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
PRIMARY
NSC
2023
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
PRIMARY
NCI_THESAURUS
C29883
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
PRIMARY
DRUG CENTRAL
3549
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
PRIMARY
CAS
98-50-0
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
PRIMARY
MERCK INDEX
m2053
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
PRIMARY Merck Index
SMS_ID
100000086603
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
PRIMARY
WIKIPEDIA
ARSANILIC ACID
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
PRIMARY
MESH
D001147
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
PRIMARY
HSDB
432
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
PRIMARY
INN
2857
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
PRIMARY
EPA CompTox
DTXSID8035138
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
PRIMARY
DRUG BANK
DB03006
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
PRIMARY
CHEBI
49477
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
PRIMARY
PUBCHEM
7389
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
PRIMARY
ECHA (EC/EINECS)
202-674-3
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
PRIMARY
EVMPD
SUB05571MIG
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
PRIMARY
FDA UNII
UDX9AKS7GM
Created by admin on Sat Dec 16 17:02:00 UTC 2023 , Edited by admin on Sat Dec 16 17:02:00 UTC 2023
PRIMARY
Related Record Type Details
Structure of SODIUM ARSANILATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of ARSANILIC ACID
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