Roxarsone

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Roxarsone
Accession Number
DB11458
Description

Roxarsone is an organoarsenic molecule added to poultry feed. The addition of this compound to poultry feed improves weight gain and feed efficiency as well as prevent the growth of coccidian parasites. The drug is also approved in the United States for use in pigs.

Type
Small Molecule
Groups
Vet approved
Structure
Thumb
Weight
Average: 263.0365
Monoisotopic: 262.941108346
Chemical Formula
C6H6AsNO6
Synonyms
  • 2-nitro-1-hydroxybenzene-4-arsonic acid
  • 3-nitro-4-hydroxybenzenearsonic acid
  • 3-nitro-4-hydroxyphenylarsonic acid
  • 4-hydroxy-3-nitrobenzenearsonic acid
  • 4-hydroxy-3-nitrophenylarsonic acid
  • Roxarson
  • Roxarsone
  • Roxarsonum
External IDs
  • NSC-2101

Pharmacology

Indication
Not Available
Contraindications & Blackbox Warnings
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Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half-life
Not Available
Clearance
Not Available
Adverse Effects
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Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcenocoumarolThe risk or severity of bleeding can be increased when Roxarsone is combined with Acenocoumarol.
DicoumarolThe risk or severity of bleeding can be increased when Roxarsone is combined with Dicoumarol.
FluindioneThe risk or severity of bleeding can be increased when Roxarsone is combined with Fluindione.
LactuloseThe therapeutic efficacy of Lactulose can be decreased when used in combination with Roxarsone.
PhenindioneThe risk or severity of bleeding can be increased when Roxarsone is combined with Phenindione.
PhenprocoumonThe risk or severity of bleeding can be increased when Roxarsone is combined with Phenprocoumon.
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Roxarsone.
Typhoid vaccineThe therapeutic efficacy of Typhoid vaccine can be decreased when used in combination with Roxarsone.
Vibrio cholerae CVD 103-HgR strain live antigenThe therapeutic efficacy of Vibrio cholerae CVD 103-HgR strain live antigen can be decreased when used in combination with Roxarsone.
WarfarinThe risk or severity of bleeding can be increased when Roxarsone is combined with Warfarin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

Products

International/Other Brands
3-Nitro / Ren-O-Sal

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as nitrophenols. These 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
Organic compounds
Super Class
Benzenoids
Class
Phenols
Sub Class
Nitrophenols
Direct Parent
Nitrophenols
Alternative Parents
Nitrobenzenes / Nitroaromatic compounds / 1-hydroxy-2-unsubstituted benzenoids / Pentaorganoarsanes / Propargyl-type 1,3-dipolar organic compounds / Oxygen-containing organoarsenic compounds / Organic oxoazanium compounds / Organic metalloid salts / Organopnictogen compounds / Organooxygen compounds
show 3 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / Allyl-type 1,3-dipolar organic compound / Aromatic homomonocyclic compound / C-nitro compound / Hydrocarbon derivative / Monocyclic benzene moiety / Nitroaromatic compound / Nitrobenzene / Nitrophenol / Organic 1,3-dipolar compound
show 14 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
C-nitro compound, phenols, organoarsonic acid (CHEBI:35817)

Chemical Identifiers

UNII
H5GU9YQL7L
CAS number
121-19-7
InChI Key
XMVJITFPVVRMHC-UHFFFAOYSA-N
InChI
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)
IUPAC Name
(4-hydroxy-3-nitrophenyl)arsonic acid
SMILES
OC1=C(C=C(C=C1)[As](O)(O)=O)N(=O)=O

References

General References
  1. Bednar AJ, Garbarino JR, Ferrer I, Rutherford DW, Wershaw RL, Ranville JF, Wildeman TR: Photodegradation of roxarsone in poultry litter leachates. Sci Total Environ. 2003 Jan 20;302(1-3):237-45. [PubMed:12526912]
  2. Garbarino JR, Bednar AJ, Rutherford DW, Beyer RS, Wershaw RL: Environmental fate of roxarsone in poultry litter. I. Degradation of roxarsone during composting. Environ Sci Technol. 2003 Apr 15;37(8):1509-14. [PubMed:12731831]
  3. Andra SS, Makris KC, Quazi S, Sarkar D, Datta R, Bach SB: Organocopper complexes during roxarsone degradation in wastewater lagoons. Environ Sci Pollut Res Int. 2010 Jun;17(5):1167-73. doi: 10.1007/s11356-009-0281-7. Epub 2010 Jan 23. [PubMed:20099042]
  4. Guo Q, Liu L, Hu Z, Chen G: Biological phosphorus removal inhibition by roxarsone in batch culture systems. Chemosphere. 2013 Jun;92(1):138-42. doi: 10.1016/j.chemosphere.2013.02.029. Epub 2013 Mar 14. [PubMed:23498058]
  5. Cortinas I, Field JA, Kopplin M, Garbarino JR, Gandolfi AJ, Sierra-Alvarez R: Anaerobic biotransformation of roxarsone and related N-substituted phenylarsonic acids. Environ Sci Technol. 2006 May 1;40(9):2951-7. [PubMed:16719096]
  6. Authors unspecified: NTP Toxicology and Carcinogenesis Studies of Roxarsone (CAS No. 121-19-7) in F344/N Rats and B6C3F1 Mice (Feed Studies). Natl Toxicol Program Tech Rep Ser. 1989 Mar;345:1-198. [PubMed:12724787]
  7. Rutherford DW, Bednar AJ, Garbarino JR, Needham R, Staver KW, Wershaw RL: Environmental fate of roxarsone in poultry litter. Part II. Mobility of arsenic in soils amended with poultry litter. Environ Sci Technol. 2003 Apr 15;37(8):1515-20. [PubMed:12731832]
  8. Basu P, Ghosh RN, Grove LE, Klei L, Barchowsky A: Angiogenic potential of 3-nitro-4-hydroxy benzene arsonic acid (roxarsone). Environ Health Perspect. 2008 Apr;116(4):520-3. doi: 10.1289/ehp.10885. [PubMed:18414637]
  9. Chen D, Zhang H, Tao Y, Wang Y, Huang L, Liu Z, Pan Y, Peng D, Wang X, Dai M, Yuan Z: Development of a high-performance liquid chromatography method for the simultaneous quantification of four organoarsenic compounds in the feeds of swine and chicken. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Apr 1;879(11-12):716-20. doi: 10.1016/j.jchromb.2011.02.013. Epub 2011 Feb 13. [PubMed:21388897]
  10. George GM, Morrison JL: Spectrophotometric determination of roxarsone in animal feeds. J Assoc Off Anal Chem. 1971 Jan;54(1):80-5. [PubMed:5170701]
  11. Zhang Y, Wang Y, Lu Q, Xin W, Cui W, Zhu J: Organoarsenic Roxarsone Promotes Angiogenesis In Vivo. Basic Clin Pharmacol Toxicol. 2016 Apr;118(4):259-70. doi: 10.1111/bcpt.12501. Epub 2015 Nov 13. [PubMed:26450128]
  12. Blakley BR, Clark EG, Fairley R: Roxarsone (3-nitro-4-hydroxyphenylarsonic acid) poisoning in pigs. Can Vet J. 1990 May;31(5):385-7. [PubMed:17423588]
  13. Kowalski LM, Reid WM: Effects of roxarsone on pigmentation and coccidiosis in broilers. Poult Sci. 1975 Sep;54(5):1544-9. [PubMed:1187515]
  14. Kowalski LM, Reid WM: Roxarsone: efficacy against Eimeria brunetti infections in chickens. Poult Sci. 1972 Sep;51(5):1586-9. [PubMed:4645728]
  15. Yannai, Shmuel (2003). Dictionary of Food Compounds with : Additives, Flavors, and Ingredients. CRC Press LLC. [ISBN:1584884169]
Human Metabolome Database
HMDB0033205
KEGG Drug
D05771
ChemSpider
4925
BindingDB
50239376
RxNav
1314413
ChEBI
35817
ChEMBL
CHEMBL1321154
Wikipedia
Roxarsone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.86 mg/mLALOGPS
logP0.17ALOGPS
logP0.6ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.43ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area123.58 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.35 m3·mol-1ChemAxon
Polarizability18.08 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Drug created on February 25, 2016 11:55 / Updated on June 12, 2020 10:53

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