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Record Information
Version1.0
Creation Date2009-03-06 18:58:30 UTC
Update Date2016-11-09 01:08:12 UTC
Accession NumberCHEM000265
Identification
Common NameSodium arsanilate
ClassSmall Molecule
DescriptionSodium arsanilate is an arsenic compound used mainly in veterinary medicine as an anthelmintic. it is also used as a growth promoter in animal feed.
Contaminant Sources
  • IARC Carcinogens Group 3
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Arsenic Compound
  • Food Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organometallic
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
(4-Aminophenyl)arsonic acid sodium saltChEBI
ArsaminChEBI
Arsanilic acid sodium saltChEBI
AtoxylChEBI
Monosodium (4-aminophenyl)arsonateChEBI
Sodium aminarsonateChEBI
Sodium anilarsonateChEBI
Sodium hydrogen 4-aminophenylarsonateChEBI
Sodium p-aminophenylarsonateChEBI
(4-Aminophenyl)arsonate sodium saltGenerator
Arsanilate sodium saltGenerator
Monosodium (4-aminophenyl)arsonic acidGenerator
Sodium aminarsonic acidGenerator
Sodium anilarsonic acidGenerator
Sodium hydrogen 4-aminophenylarsonic acidGenerator
Sodium p-aminophenylarsonic acidGenerator
Sodium arsanilic acidGenerator
Arsenilate, sodiumMeSH
4 Aminobenzenearsonic acidMeSH
4-Aminobenzenearsonic acidMeSH
Acid, arsanilicMeSH
Arsanilate, sodiumMeSH
Acid, P-aminophenylarsonicMeSH
Sodium arsenilateMeSH
Acid, 4-aminobenzenearsonicMeSH
Arsanilic acidMeSH
P Aminophenylarsonic acidMeSH
P-Aminophenylarsonic acidMeSH
Chemical FormulaC6H7AsNNaO3
Average Molecular Mass239.036 g/mol
Monoisotopic Mass238.954 g/mol
CAS Registry Number127-85-5
IUPAC Namesodium hydrogen (4-aminophenyl)arsonate
Traditional Nameatoxyl
SMILESNC1=CC=C(C=C1)[As](O)(=O)O[Na]
InChI IdentifierInChI=1S/C6H8AsNO3.Na/c8-6-3-1-5(2-4-6)7(9,10)11;/h1-4H,8H2,(H2,9,10,11);/q;+1/p-1
InChI KeyOUFRIWNNMFWZTM-UHFFFAOYSA-M
Chemical Taxonomy
Description belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAniline and substituted anilines
Direct ParentAniline and substituted anilines
Alternative Parents
Substituents
  • Aniline or substituted anilines
  • Pentaorganoarsane
  • Organic metalloid salt
  • Organic alkali metal salt
  • Oxygen-containing organoarsenic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Amine
  • Organic sodium salt
  • Organic nitrogen compound
  • Organic salt
  • Organic zwitterion
  • Primary amine
  • Organonitrogen compound
  • Organoarsenic compound
  • Organic oxide
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility167 mg/mL [MERCK INDEX (1996)]
Predicted Properties
PropertyValueSource
Water Solubility21.8 g/LALOGPS
logP0.07ALOGPS
logP1.15ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)4.96ChemAxon
pKa (Strongest Basic)2.83ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area72.55 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity35.53 m³·mol⁻¹ChemAxon
Polarizability17.89 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-961f6b6c3fe43c1f2e03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0072-0890000000-5cf4811d19b37d8f7a01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01z9-9440000000-fa5c6597bdc494f4700fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-6970000000-8ab280dd9081a0b86074View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2090000000-658e0ef05361ecaaa573View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9200000000-dcfcfb60252b420745acView in MoNA
Toxicity Profile
Route of ExposureOral (6) ; inhalation (6); dermal (6)
Mechanism of ToxicityArsenic and its metabolites disrupt ATP production through several mechanisms. At the level of the citric acid cycle, arsenic inhibits pyruvate dehydrogenase and by competing with phosphate it uncouples oxidative phosphorylation, thus inhibiting energy-linked reduction of NAD+, mitochondrial respiration, and ATP synthesis. Hydrogen peroxide production is also increased, which might form reactive oxygen species and oxidative stress. Arsenic's carcinogenicity is influenced by the arsenical binding of tubulin, which results in aneuploidy, polyploidy and mitotic arrests. The binding of other arsenic protein targets may also cause altered DNA repair enzyme activity, altered DNA methylation patterns and cell proliferation. (4, 2)
MetabolismArsenic 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. (7)
Toxicity ValuesLD50: 75 mg/kg (Subcutaneous, Rat) LD50: 335 mg/kg (Intravenous, Rat)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (5)
Uses/SourcesSodium arsanilate is found in animal feed, and is also used in veterinary medicine, mainly to treat swine dysentry.
Minimum Risk LevelAcute Oral: 0.005 mg/kg/day (8) Chronic Oral: 0.0003 mg/kg/day (8) Chronic Inhalation: 0.01 mg/m3 (8)
Health EffectsHypovolemia from capillary leakage (third-spacing of fluids) is a common, serious, early effect. Muscle cramps, facial edema, bronchitis, dyspnea, chest pain, dehydration, intense thirst, and fluid-electrolyte disturbances are also common following significant exposures. A garlic-like odor of the breath and feces may also occur. After absorption, arsenic may cause multi-organ failure by inhibiting sulfhydryl-containing enzymes. Encephalopathy, with headache, lethargy, mental confusion, hallucinations, emotional lability, memory loss and delirium may occur; seizures, stupor, convulsions, coma, and death may follow within 24 hours of a severe acute exposure. Dysrhythmias (particularly QTc prolongation and torsade de pointes), cardiomyopathy, ARDS, hepatitis, rhabdomyolysis, hemolysis, and renal failure may develop over several days. The sequence of chronic poisoning involves hyperpigmentation, and eczematoid and allergic dermatitis. muscle fasciculations; gross tremors; ataxia; incoordination; and mental confusion. Muscular weakness, limb tenderness and difficulty walking may follow. The final phase consists of peripheral sensory neuropathy of the hands and feet. That may be associated with a motor neuropathy as well (3).
SymptomsInitial signs and symptoms of arsenic ingestion include burning lips, throat constriction and dysphagia, followed by excruciating abdominal pain, hemorrhagic gastritis, gastroenteritis, severe nausea, projectile voting, profuse "rice water-like" diarrhea, with hypovolemia that may result in hypotension and an irregular pulse. The sequence of chronic poisoning involves weakness, anorexia, hepatomegaly, jaundice, and gastrointestinal complaints, followed by conjunctivitis, irritation of the throat and respiratory tract. ther effects of chronic exposure include conjunctivitis with irritation and lacrimation; hair, skin and nail changes; hyperkeratosis of feet and hands; and melanosis, with pigment spots in corneal and conjunctival epithelium. Peripheral nervous system symptoms may include numbness, burning, and tingling of the hands and feet; pain; paresthesias; tenderness (3).
TreatmentAggressive decontamination with gastric lavage is recommended if the patient has consumed a potentially life-threatening dose and if the patient is not vomiting. Administer charcoal as a slurry (3).
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID36049
PubChem Compound ID23158
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available