Basic information
- CAS
97-44-9- Standard SMILES
CC(=O)Nc1cc([As](=O)(O)O)ccc1O- InChIKey
ODFJOVXVLFUVNQ-UHFFFAOYSA-N- Molecular formula
- C8H10AsNO5
- Average molar mass
- 275.09 g/mol
- Monoisotopic mass
- 274.977492
Overview
Acetarsol is an anilide and a member of acetamides.
Names & identifiers
- Preferred name
- Acetarsol
- IUPAC
- (3-acetamido-4-hydroxyphenyl)arsonic acid
- English name
- ACETARSONE
- Molecular formula
- C8H10AsNO5
- Molecular weight
- 275.09
Names & synonyms
acetarsolAcetarsone97-44-9AcetphenarsineStovarsolAmarsanArsaphenAmoebalN-Acetyl-4-hydroxy-m-arsanilic acidDynarsanGynoplixKharophen
Show more names
vagiseptsvc190ff190goylamasanOracidAmassn
LimarsolMalagrideDeveganMexylDisparicidaGinarsolKubarsolMonargan
Database identifiers
- CAS
97-44-9- PubChem CID
- 1985
- DTXSID
DTXSID9045847- ChEMBL
CHEMBL1330792- ChEBI
CHEBI:135135- UNII
- 806529YU1N
- EC Number
- 202-582-3
- Nikkaji
- J1.495H
Properties
Computed structural properties
- Topological polar surface area
- 107 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 289
Experimental & physicochemical properties
Solubility
Slightly soluble
>41.3 [ug/mL] (The mean of the results at pH 7.4)
Melting Point225-227 ºC
Collision Cross Section
151.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
153.02 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 220.5 °C · 220.5°C
- Boiling point
- 72.17 °C · 72.17°C
- Density
- 1.0325 g/cm3 · 1.0325 g/cm3(Temp: 15 °C)
- storage temp.
- Store at RT
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
- form
- solid
- pka
- 3.73 · pKa 3.73 (H2O t=26) (Uncertain);7.9 (Uncertain); 9.3(H2O) (Uncertain)
- color
- Crystalline material
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H228 (36.1%): Flammable solid [Danger Flammable solids]
P210, P240, P241, P261, P264, P270, P271, P273, P280, P301+P316, P304+P340, P316, P321, P330, P370+P378, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 61 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationRestricted substance: Acetarsol
Other Safety InformationIMAP assessments - Arsonic acid, [3-(acetylamino)-4-hydroxyphenyl]-: Environment tier I assessment
Hazard Classes and CategoriesFlam. Sol. 1 (36.1%)
Safety & protection
Minimum Risk LevelAcute Oral: 0.005 mg/kg/day (L134)
Chronic Oral: 0.0003 mg/kg/day (L134)
Chronic Inhalation: 0.01 mg/m3 (L134)
Toxicology
Treatment
Arsenic poisoning can be treated by chelation therapy, using chelating agents such as dimercaprol, EDTA or DMSA. Charcoal tablets may also be used for less severe cases. In addition, maintaining a diet high in sulfur helps eliminate arsenic from the body. (L20)
Health EffectsArsenic poisoning can lead to death from multi-system organ failure, probably from necrotic cell death, not apoptosis. Arsenic is also a known carcinogen, esepcially in skin, liver, bladder and lung cancers. (T1, L20)
Chemistry & industry
Pharmacology
ATC Code
G - Genito urinary system and sex hormones
P - Antiparasitic products, insecticides and repellents
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
QG - Genito urinary system and sex hormones
QP - Antiparasitic products, insecticides and repellents
Protein BindingThis pharmacokinetic property was not addressed.
PharmacodynamicsSome reports indicate a certain infection remission with the use of acetarsol but this reports also demonstrate the absorption of systemic arsenic which can be physiologically dangerous.
Mechanism of Action
The mechanism of action of acetarsol is not well known but it is thought to bind to protein-containing sulfhydryl groups located in the infective microorganism and to form a lethal As-S bond. The formation of this bond impairs the protein to function and it eventually kills the microorganism.
Biological Half-LifeThis pharmacokinetic property was not addressed.
Metabolism/Metabolites
This pharmacokinetic property was not addressed.
Arsenic is absorbed mainly by inhalation or ingestion, as to a lesser extent, dermal exposure. It is then distributed throughout the body, where it is reduced into arsenite if necessary, then methylated into monomethylarsenic (MMA) and dimethylarsenic acid (DMA) by arsenite methyltransferase. Arsenic and its metabolites are primarily excreted in the urine. Arsenic is known to induce the metal-binding protein metallothionein, which decreases the toxic effects of arsenic and other metals by binding them and making them biologically inactive, as well as acting as an antioxidant. (L20)
MeSH Pharmacological ClassificationSubstances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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