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Sulfaquinoxaline

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Identification

Generic Name
Sulfaquinoxaline
DrugBank Accession Number
DB11464
Background

Sulfaquinoxaline is a veterinary medicine which can be given to cattle and sheep to treat coccidiosis.It is available in Pakistan with Sanna Laboratories in combination with Amprolium and Vitamin K as potential treatment of coccidiosis.

Type
Small Molecule
Groups
Vet approved
Structure
3D
Similar Structures
Weight
Average: 300.336
Monoisotopic: 300.068096338
Chemical Formula
C14H12N4O2S
Synonyms
  • Sulfaquinoxaline
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Pharmacology

Indication

Not Available

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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

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.
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interactions in your software
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Sulfaquinoxaline.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Sulfaquinoxaline.
AlbiglutideThe therapeutic efficacy of Albiglutide can be increased when used in combination with Sulfaquinoxaline.
AlogliptinThe therapeutic efficacy of Alogliptin can be increased when used in combination with Sulfaquinoxaline.
BenzylpenicillinSulfaquinoxaline may decrease the excretion rate of Benzylpenicillin which could result in a higher serum level.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Sulfaquinoxaline sodium21223EPJ40967-80-6WXUQBKOBXREBBX-UHFFFAOYSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as quinoxalines. These are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazanaphthalenes
Sub Class
Benzodiazines
Direct Parent
Quinoxalines
Alternative Parents
Benzenesulfonamides / Benzenesulfonyl compounds / Aniline and substituted anilines / Pyrazines / Imidolactams / Sulfonyls / Organosulfonic acids and derivatives / Heteroaromatic compounds / Azacyclic compounds / Primary amines
show 3 more
Substituents
Amine / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Azacycle / Benzenesulfonamide / Benzenesulfonyl group / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Imidolactam
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
WNW8115TM9
CAS number
59-40-5
InChI Key
NHZLNPMOSADWGC-UHFFFAOYSA-N
InChI
InChI=1S/C14H12N4O2S/c15-10-5-7-11(8-6-10)21(19,20)18-14-9-16-12-3-1-2-4-13(12)17-14/h1-9H,15H2,(H,17,18)
IUPAC Name
4-amino-N-(quinoxalin-2-yl)benzene-1-sulfonamide
SMILES
NC1=CC=C(C=C1)S(=O)(=O)NC1=NC2=C(C=CC=C2)N=C1

References

General References
  1. Righter HF, Worthington JM, Zimmerman HE Jr, Mercer HD: Tissue-residue depletion of sulfaquinoxaline in poultry. Am J Vet Res. 1970 Jun;31(6):1051-4. [Article]
  2. Rutczynska-Skonieczna EM: [Detection of sulfaquinoxaline residues in eggs]. Rocz Panstw Zakl Hig. 1979;30(2):137-40. [Article]
  3. Rutczynska-Skonieczna EM: [Detection of sulfaquinoxaline residues in poultry meat]. Rocz Panstw Zakl Hig. 1977;28(1):59-63. [Article]
  4. Kahn SG, Actor P: Enhancement of sulfaquinoxaline activity by nystatin. Poult Sci. 1966 May;45(3):581-2. [Article]
  5. Brown MJ, Wojcik B, Burgess EC, Smith GJ: Adverse reactions to sulfaquinoxaline in coyote pups--. J Am Vet Med Assoc. 1982 Dec 1;181(11):1419-20. [Article]
  6. Authors unspecified: VITAMIN K and sulfaquinoxaline poisoning in chickens. Nutr Rev. 1956 Aug;14(8):240-1. [Article]
  7. MUSHETT CW, SEELER AO: Hypoprothrombinemia resulting from the administration of sulfaquinoxaline. J Pharmacol Exp Ther. 1947 Sep;91(1):84-91. [Article]
  8. HAGEN KW Jr: The effects of continuous sulfaquinoxaline feeding on rabbit mortality. Am J Vet Res. 1958 Apr;19(71):494-6. [Article]
  9. STOWE CM, PALLESEN D, HARTMAN W: Studies on the pharmacology of sulfaquinoxaline in dairy cattle. Am J Vet Res. 1957 Jul;18(68):511-8. [Article]
  10. Berzas Nevado JJ, Castaneda Penalvo G, Guzman Bernardo FJ: Simultaneous determination of sulfaquinoxaline, sulfamethazine and pyrimethamine by liquid chromatography. J Chromatogr A. 2000 Feb 18;870(1-2):169-77. [Article]
  11. Le Fur C, Legeret B, de Sainte Claire P, Wong-Wah-Chung P, Sarakha M: Liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometry for the analysis of sulfaquinoxaline byproducts formed in water upon solar light irradiation. Rapid Commun Mass Spectrom. 2013 Mar 30;27(6):722-30. doi: 10.1002/rcm.6507. [Article]
  12. Costi EM, Sicilia MD, Rubio S: Multiresidue analysis of sulfonamides in meat by supramolecular solvent microextraction, liquid chromatography and fluorescence detection and method validation according to the 2002/657/EC decision. J Chromatogr A. 2010 Oct 1;1217(40):6250-7. doi: 10.1016/j.chroma.2010.08.017. Epub 2010 Aug 13. [Article]
  13. De Liguoro M, Di Leva V, Gallina G, Faccio E, Pinto G, Pollio A: Evaluation of the aquatic toxicity of two veterinary sulfonamides using five test organisms. Chemosphere. 2010 Oct;81(6):788-93. doi: 10.1016/j.chemosphere.2010.07.003. Epub 2010 Jul 31. [Article]
  14. Herrera-Herrera AV, Hernandez-Borges J, Borges-Miquel TM, Rodriguez-Delgado MA: Dispersive liquid-liquid microextraction combined with ultra-high performance liquid chromatography for the simultaneous determination of 25 sulfonamide and quinolone antibiotics in water samples. J Pharm Biomed Anal. 2013 Mar 5;75:130-7. doi: 10.1016/j.jpba.2012.11.026. Epub 2012 Nov 23. [Article]
  15. Gaudin V, De Courville A, Hedou C, Rault A, Diomande SE, Creff-Froger C, Verdon E: Evaluation and validation of two microbiological tests for screening antibiotic residues in honey according to the European guideline for the validation of screening methods. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2013;30(2):234-43. doi: 10.1080/19440049.2012.738367. Epub 2012 Nov 6. [Article]
  16. Guinee P, Kruyt B: Use of an isolator system to study the selective pressure of sulfaquinoxalin-containing coccidiostats on Escherichia coli populations in chicks. Zentralbl Veterinarmed B. 1975 Nov;22(9):718-28. [Article]
  17. Sun L, Sun X, Du X, Yue Y, Chen L, Xu H, Zeng Q, Wang H, Ding L: Determination of sulfonamides in soil samples based on alumina-coated magnetite nanoparticles as adsorbents. Anal Chim Acta. 2010 Apr 30;665(2):185-92. doi: 10.1016/j.aca.2010.03.044. Epub 2010 Mar 27. [Article]
  18. Guo Y, Ngom B, Le T, Jin X, Wang L, Shi D, Wang X, Bi D: Utilizing three monoclonal antibodies in the development of an immunochromatographic assay for simultaneous detection of sulfamethazine, sulfadiazine, and sulfaquinoxaline residues in egg and chicken muscle. Anal Chem. 2010 Sep 15;82(18):7550-5. doi: 10.1021/ac101020y. [Article]
  19. Raich-Montiu J, Beltran JL, Prat MD, Granados M: Studies on the extraction of sulfonamides from agricultural soils. Anal Bioanal Chem. 2010 May;397(2):807-14. doi: 10.1007/s00216-010-3580-4. Epub 2010 Mar 10. [Article]
  20. Ghorab MM, Ragab FA, Heiba HI, El-Gazzar MG, El-Gazzar MG: Synthesis, in vitro anticancer screening and radiosensitizing evaluation of some new 4-[3-(substituted)thioureido]-N-(quinoxalin-2-yl)-benzenesulfonamide derivatives. Acta Pharm. 2011 Dec;61(4):415-25. doi: 10.2478/v10007-011-0040-4. [Article]
  21. Tolika EP, Samanidou VF, Papadoyannis IN: Development and validation of an HPLC method for the determination of ten sulfonamide residues in milk according to 2002/657/EC. J Sep Sci. 2011 Jul;34(14):1627-35. doi: 10.1002/jssc.201100171. Epub 2011 Jun 3. [Article]
  22. Wei R, Ge F, Huang S, Chen M, Wang R: Occurrence of veterinary antibiotics in animal wastewater and surface water around farms in Jiangsu Province, China. Chemosphere. 2011 Mar;82(10):1408-14. doi: 10.1016/j.chemosphere.2010.11.067. Epub 2010 Dec 14. [Article]
  23. Li H, Kijak PJ: Development of a quantitative multiclass/multiresidue method for 21 veterinary drugs in shrimp. J AOAC Int. 2011 Mar-Apr;94(2):394-406. [Article]
  24. Luders H, Lai KW, Hinz KH: [Blood and tissue content of sulfamethazine and sulfaquineoxaline in broilers following medication with drinking water. A contribution to mass medication in poultry]. Zentralbl Veterinarmed B. 1974 Jan-Feb;21(1):110-8. [Article]
  25. Gaudin V, Rault A, Verdon E: Validation of a commercial receptor kit Sulfasensor Honey for the screening of sulfonamides in honey according to Commission Decision 2002/657/EC. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2012;29(6):942-50. doi: 10.1080/19440049.2012.668718. Epub 2012 Mar 29. [Article]
  26. Ghorab MM, Ragab FA, Heiba HI, El-Gazzar MG, El-Gazzar MG: Synthesis, in-vitro anticancer screening and radiosensitizing evaluation of some new N-(quinoxalin-2-yl)benzenesulfonamide derivatives. Arzneimittelforschung. 2012 Jan;62(1):46-52. doi: 10.1055/s-0031-1295496. Epub 2012 Jan 10. [Article]
  27. Kumar P, Companyo R: Development and validation of an LC-UV method for the determination of sulfonamides in animal feeds. Drug Test Anal. 2012 May;4(5):368-75. doi: 10.1002/dta.296. Epub 2011 Jun 14. [Article]
  28. Wang L, Wu J, Wang Q, He C, Zhou L, Wang J, Pu Q: Rapid and sensitive determination of sulfonamide residues in milk and chicken muscle by microfluidic chip electrophoresis. J Agric Food Chem. 2012 Feb 22;60(7):1613-8. doi: 10.1021/jf2036577. Epub 2012 Feb 8. [Article]
  29. Yu H, Tao Y, Chen D, Wang Y, Huang L, Peng D, Dai M, Liu Z, Wang X, Yuan Z: Development of a high performance liquid chromatography method and a liquid chromatography-tandem mass spectrometry method with the pressurized liquid extraction for the quantification and confirmation of sulfonamides in the foods of animal origin. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Sep 1;879(25):2653-62. doi: 10.1016/j.jchromb.2011.07.032. Epub 2011 Jul 30. [Article]
  30. Jia A, Hu J, Wu X, Peng H, Wu S, Dong Z: Occurrence and source apportionment of sulfonamides and their metabolites in Liaodong Bay and the adjacent Liao River basin, North China. Environ Toxicol Chem. 2011 Jun;30(6):1252-60. doi: 10.1002/etc.508. Epub 2011 Apr 11. [Article]
  31. Yannai, Shmuel (2003). Dictionary of Food Compounds with : Additives, Flavors, and Ingredients. CRC Press LLC. [ISBN:1584884169]
Human Metabolome Database
HMDB0033139
KEGG Drug
D05952
ChemSpider
5147
RxNav
1306111
ChEBI
94719
ChEMBL
CHEMBL1437847
ZINC
ZINC000000002106
Wikipedia
Sulfaquinoxaline

Clinical Trials

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Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionOral
Powder
SolutionOral
SolutionOral60 mg/mL
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0761 mg/mLALOGPS
logP1.24ALOGPS
logP1.55Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)6.79Chemaxon
pKa (Strongest Basic)2.13Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area97.97 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity79.3 m3·mol-1Chemaxon
Polarizability29.46 Å3Chemaxon
Number of Rings3Chemaxon
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-MSsplash10-0le9-5941000000-8eb0fa3a436056b37a70
GC-MS Spectrum - EI-BGC-MSsplash10-000i-8490000000-cc9214994a8554fe8414
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0309000000-e99ee5535b4328e62ba7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-387e6d972d4702baab4b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pb9-0907000000-7bc42f763d4c4b04ae57
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-3f38d09ae2465799b555
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kb-4900000000-baadd11778585ee7a393
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0005-4910000000-3000c9feb8ccae6ce5ee
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-181.6772248
predicted
DarkChem Lite v0.1.0
[M-H]-181.7263248
predicted
DarkChem Lite v0.1.0
[M-H]-181.7639248
predicted
DarkChem Lite v0.1.0
[M-H]-167.29234
predicted
DeepCCS 1.0 (2019)
[M+H]+182.1247248
predicted
DarkChem Lite v0.1.0
[M+H]+182.3666248
predicted
DarkChem Lite v0.1.0
[M+H]+182.8301248
predicted
DarkChem Lite v0.1.0
[M+H]+169.65034
predicted
DeepCCS 1.0 (2019)
[M+Na]+181.9261248
predicted
DarkChem Lite v0.1.0
[M+Na]+181.7352248
predicted
DarkChem Lite v0.1.0
[M+Na]+176.54083
predicted
DeepCCS 1.0 (2019)

Drug created at February 25, 2016 18:58 / Updated at February 21, 2021 18:53