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Details

Stereochemistry ACHIRAL
Molecular Formula C8H10AsNO5
Molecular Weight 275.0903
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACETARSOL

SMILES

CC(=O)NC1=CC(=CC=C1O)[As](O)(O)=O

InChI

InChIKey=ODFJOVXVLFUVNQ-UHFFFAOYSA-N
InChI=1S/C8H10AsNO5/c1-5(11)10-7-4-6(9(13,14)15)2-3-8(7)12/h2-4,12H,1H3,(H,10,11)(H2,13,14,15)

HIDE SMILES / InChI

Description

Acetarsone is a pentavalent arsenical compound with antiprotozoal and antihelmintic properties. It was first discovered in 1921 at Pasteur Institute by Ernest Fourneau, and sold under the brand name Stovarsol (fourneau is the French word for stove). Before stovarsol was used in the treatment of congenital syphilis, it had already been used in other diseases : amoebiasis, acquired syphilis, yaws, trypanosomiasis and malaria, and a formidable list of toxic manifestations can be compiled from the literature. Bender (I927) recorded six cases of poisoning with malaise, fever, cedema, jaundice, diarrhoea, albuminuria, bronchitis, coryza and skin troubles, such as diffuse erythema, dryness and pruritus. Of 232 cases of amoebiasis treated by Brown (I935) without a death, thirteen (5.6%) had toxic erythemata, some of them so severe as to amount to exfoliative dermatitis. Although its mechanism of action is not fully known, acetarsone may bind to protein-containing sulfhydryl groups located in the parasite, thereby forming lethal As-S bonds. This may prevent their functioning and eventually kill the parasite.

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
one to four grains
Route of Administration: Oral
In Vitro Use Guide
Unknown