Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H12N4O2S |
Molecular Weight | 300.336 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=CC=C(C=C1)S(=O)(=O)NC2=NC3=CC=CC=C3N=C2
InChI
InChIKey=NHZLNPMOSADWGC-UHFFFAOYSA-N
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)
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/18837573Curator's Comment: description was created based on several sources, including
http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm064903.pdf
Sources: http://www.ncbi.nlm.nih.gov/pubmed/18837573
Curator's Comment: description was created based on several sources, including
http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm064903.pdf
Sulfaquinoxaline is a veterinary drug, which can be given to animals to treat coccidiosis and Acute Fowl cholera. It has often used in combinations with others drugs. It had its origins in the chemical synthetic program that sprang from the introduction of sulfonamide drugs into human medicine in the 1930s. The program was sustained through the years of World War II despite declining clinical use of that chemical class. Several sulfa drugs were known to be active against the sporozoan parasite (Plasmodium spp.) that causes malaria, but were not satisfactory in clinical practice. A sulfonamide that had a long plasma half-life would ipso facto be considered promising as an antimalarial drug. Sulfaquinoxaline, synthesized during the war, was such a compound. It proved too toxic to be used in human malaria, but was found to be a superior agent against another sporozoan parasite, Eimeria spp., the causative agent of coccidiosis in domestic chickens. In 1948 sulfaquinoxaline was introduced commercially as a poultry coccidiostat. The action mechanism of sulfaquinoxaline is to inhibit the dihydrofolate synthetase to encumber the nucleate synthesis of bacterium and coccidian its active peak to coccidian is at the second schizont stage (the fourth day of coccidial life cycle), so it will not affect the anti-coccidial immunity in chicken.
Originator
Sources: http://www.ncbi.nlm.nih.gov/pubmed/18837573
Curator's Comment: # At Merck, chemist Max Tishler and his associate John Weijlard in the 1930s
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Batcerial dihydrofolate synthetase Sources: http://www.kdqchem.com/pages/pro4-8.htm |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | Unknown Approved UseUnknown |
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Curative | POULTRYSULFA Soluble Powder Approved UseAcute Fowl cholera – TURKEYS AND CHICKENS: As an aid in the control of acute fowl cholera caused by Pasteurella multocida susceptible to sulfamethazine, sulfamerazine and sulfaquinoxaline. Coccidiosis – TURKEYS: As an aid in the control of coccidiosis caused by Eimeria meleagrimitis and E. adenoeides susceptible to sulfamethazine, sulfamerazine, and sulfaquinoxaline. Coccidiosis – CHICKENS: As an aid in the control of coccidiosis caused by Eimeria tenella and E. necatrix susceptible to sulfamethazine, sulfamerazine, and sulfaquinoxaline. |
PubMed
Title | Date | PubMed |
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The therapeutic effect of 16 antimicrobial agents on Cryptosporidium infection in mice. | 1982 Apr |
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In vitro cultivation of Cryptosporidium parvum and screening for anticryptosporidial drugs. | 1990 Aug |
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Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro. | 1996 Dec |
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Confirmatory analysis of sulfonamide antibacterials in bovine liver and kidney: extraction with hot water and liquid chromatography coupled to a single- or triple-quadrupole mass spectrometer. | 2003 |
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Determination of some sulfonamides and trimethoprim in chicken, fish muscle and eggs by liquid chromatography-tandem mass spectrometry. | 2004 Apr-Jun |
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Multiresidue determination of sulfonamides in a variety of biological matrices by supported liquid membrane with high pressure liquid chromatography-electrospray mass spectrometry detection. | 2004 Sep 8 |
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[Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry]. | 2005 Jul |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Multiresidue determination of sulfonamides in edible catfish, shrimp and salmon tissues by high-performance liquid chromatography with postcolumn derivatization and fluorescence detection. | 2006 Aug 18 |
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Simultaneous determination of 17 sulfonamides and the potentiators ormetoprim and trimethoprim in salmon muscle by liquid chromatography with tandem mass spectrometry detection. | 2007 Jan-Feb |
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[Determination of 12 sulfonamides in cosmetics by ultra performance liquid chromatography]. | 2007 Mar |
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Determination of 10 sulfonamide residues in meat samples by liquid chromatography with ultraviolet detection. | 2007 Mar-Apr |
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Trace determination of sulfonamides residues in meat with a combination of solid-phase microextraction and liquid chromatography-mass spectrometry. | 2007 May 15 |
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[Simultaneous determination of nine sulfonamide residues in milk using solid phase extraction and high performance liquid chromatography]. | 2007 Sep |
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Application of liquid-liquid-liquid microextraction and high-performance liquid-chromatography for the determination of sulfonamides in water. | 2008 Mar 31 |
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A landmark contribution to poultry science--prophylactic control of coccidiosis in poultry. | 2009 Apr |
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Determination of ten sulphonamides in egg by liquid chromatography-tandem mass spectrometry. | 2009 Apr 1 |
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Development and validation of a confirmatory method for the determination of sulphonamides in milk by liquid chromatography with diode array detection. | 2009 Apr 1 |
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Use of capillary electrophoresis with laser-induced fluorescence detection to screen and liquid chromatography-tandem mass spectrometry to confirm sulfonamide residues: validation according to European Union 2002/657/EC. | 2009 Nov 13 |
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A confirmatory method for the simultaneous extraction, separation, identification and quantification of Tetracycline, Sulphonamide, Trimethoprim and Dapsone residues in muscle by ultra-high-performance liquid chromatography-tandem mass spectrometry according to Commission Decision 2002/657/EC. | 2009 Nov 13 |
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Determination of sulfonamides in soil samples based on alumina-coated magnetite nanoparticles as adsorbents. | 2010 Apr 30 |
Patents
Sample Use Guides
in animals: 6 mg/lb/day for 3–5 days in drinking water
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/2916837
Sulfaquinoxaline has been shown to be a potent (Ki = 1 uM) freely reversible inhibitor of the dithiothreitol-dependent reduction of both vitamin K epoxide and vitamin K quinone by rat liver microsomes in vitro. This observation provides an explanation for the hemorrhagic syndrome occasionally seen in poultry on medicated feed and the efficacy of sulfaquinoxaline in anticoagulant based rodenticides. Sulfaquinoxaline inhibition resembled inhibition by coumarin anticoagulants (e.g., warfarin) and hydroxynaphthoquinones (e.g., lapachol).
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 556.685
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WHO-VATC |
QJ01EW16
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WHO-VATC |
QP51AG53
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CFR |
21 CFR 520.2325A
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CFR |
21 CFR 520.2325
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CFR |
21 CFR 558.586
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CFR |
21 CFR 520.2218
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WHO-VATC |
QP51AG03
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EPA PESTICIDE CODE |
77901
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NCI_THESAURUS |
C29739
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CFR |
21 CFR 520.2325B
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WHO-VATC |
QJ01EQ16
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SULFAQUINOXALINE
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m10340
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PRIMARY | Merck Index |
ACTIVE MOIETY
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)