ContaminantDB: Roxarsone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (44)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:30 UTC

Update Date

2016-11-09 01:08:12 UTC

Accession Number

CHEM000260

Identification

Common Name

Roxarsone

Class

Small Molecule

Description

Roxarsone is used to control enteric infections in chicken and to improve growth and feed efficiency. Roxarsone is a fda approved additive for chicken, turkey and swine feeds.

Contaminant Sources

FooDB Chemicals
IARC Carcinogens Group 3
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Arsenic Compound
Food Toxin
Industrial/Workplace Toxin
Metabolite
Organic Compound
Organometallic
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Nitro-1-hydroxybenzene-4-arsonic acid	ChEBI
3-Nitro	ChEBI
3-Nitro-4-hydroxybenzenearsonic acid	ChEBI
3-Nitro-4-hydroxyphenylarsonic acid	ChEBI
4-Hydroxy-3-nitrobenzenearsonic acid	ChEBI
4-Hydroxy-3-nitrophenylarsonic acid	ChEBI
NSC-2101	ChEBI
Ren-O-sal	ChEBI
Roxarson	ChEBI
Roxarsonum	ChEBI
2-Nitro-1-hydroxybenzene-4-arsonate	Generator
3-Nitro-4-hydroxybenzenearsonate	Generator
3-Nitro-4-hydroxyphenylarsonate	Generator
4-Hydroxy-3-nitrobenzenearsonate	Generator
4-Hydroxy-3-nitrophenylarsonate	Generator
(4-Hydroxy-3-nitrobenzene)arsonic acid	HMDB
(4-Hydroxy-3-nitrophenyl)-arsonic acid	HMDB
2-Nitrophenol-4-arsonic acid	HMDB
3-nitro-10	HMDB
3-nitro-20	HMDB
3-nitro-50	HMDB
3-nitro-80	HMDB
3n4HPa	HMDB
4-HYDROXY-3-nitro-benzenearsonIC ACID	HMDB
4-Hydroxy-3-nitrophenyl arsonic acid	HMDB
Aklomix-3	HMDB
As-(4-hydroxy-3-nitrophenyl)-arsonic acid	HMDB
C6H6AsNO6	HMDB
nitro acid 100 per cent	HMDB
Nitrophenolarsonic acid	HMDB
Nitrophenoloarsonic acid	HMDB
NSC 2101	HMDB
Ren O-sal	HMDB
Ristat	HMDB
Roxarsone(usan)	HMDB
Roxarsone, ban, inn, usan	HMDB
Acid, 3-nitro-4-hydroxyphenylarsonic	MeSH, HMDB
3 nitro 10	MeSH, HMDB
3 nitro 4 Hydroxyphenylarsonic acid	MeSH, HMDB
3Nitro10	MeSH, HMDB

Chemical Formula

C₆H₆AsNO₆

Average Molecular Mass

263.037 g/mol

Monoisotopic Mass

262.941 g/mol

CAS Registry Number

121-19-7

IUPAC Name

(4-hydroxy-3-nitrophenyl)arsonic acid

Traditional Name

3-nitro

SMILES

OC1=C(C=C(C=C1)[As](O)(O)=O)N(=O)=O

InChI Identifier

InChI=1S/C6H6AsNO6/c9-6-2-1-4(7(10,11)12)3-5(6)8(13)14/h1-3,9H,(H2,10,11,12)

InChI Key

XMVJITFPVVRMHC-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as nitrophenols. Nitrophenols are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both a hydroxyl group and a nitro group on two different ring carbon atoms.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Nitrophenol
Nitrobenzene
Nitroaromatic compound
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Pentaorganoarsane
C-nitro compound
Organic nitro compound
Oxygen-containing organoarsenic compound
Organic oxoazanium
Organic metalloid salt
Allyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic salt
Organooxygen compound
Organonitrogen compound
Organoarsenic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

C-nitro compound (CHEBI:35817 )
phenols (CHEBI:35817 )
organoarsonic acid (CHEBI:35817 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Pale yellow solid.

Experimental Properties

Property	Value
Melting Point	300°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.86 g/L	ALOGPS
logP	0.17	ALOGPS
logP	0.6	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	123.58 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.35 m³·mol⁻¹	ChemAxon
Polarizability	18.08 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-1790000000-f715c8649a77c00beb03	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-7495000000-960cbe4266d513123513	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0006-0190000000-88bf28abdc541f278873	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0f6x-0890000000-47126f3e1c9cf9440afc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-05fr-2900000000-7502d3e66b8a204dcfde	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0zmi-0900000000-9eaa83883e1374b2a22c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0a4j-4900000000-73c97b0591ba3548ce73	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0aba-4900000000-625b3990a2d44b3440a0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0f6x-0890000000-c0198066c21a444a325e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0090000000-7283a1d879b75c66222f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-0090000000-39a3f59584592464e81f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bt9-0490000000-87933a723d1263ada5d5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-965c468eb37bebb7ec67	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0090000000-06c411aff1d24a3623e6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-5940000000-d34c64ce51c0e25129a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0090000000-0d1de734f0360de6fadd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0090000000-1989c13e3d39374e05b9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002r-9100000000-d15122f048164952f52f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0090000000-52aea2c6a5a77a1fa17e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0090000000-52aea2c6a5a77a1fa17e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-0900000000-9f20db1f83edf6d96931	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (2) ; inhalation (2); dermal (2)

Mechanism of Toxicity

Arsenic 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. (7, 1)

Metabolism

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. (3)

Toxicity Values

LD50: 81 mg/kg (Oral, Rat)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (6)

Uses/Sources

3-nitro-4-hydroxy-phenyl-arsonic acid is found in poultry feed.

Minimum Risk Level

Acute Oral: 0.005 mg/kg/day (5) Chronic Oral: 0.0003 mg/kg/day (5) Chronic Inhalation: 0.01 mg/m3 (5)

Health Effects

Hypovolemia 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 (8).

Symptoms

Initial 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 (8).

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. (3)

Concentrations

Not Available

External Links

DrugBank ID

DB11458

HMDB ID

HMDB0033205

FooDB ID

FDB011218

Phenol Explorer ID

Not Available

KNApSAcK ID