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Details

Stereochemistry ACHIRAL
Molecular Formula C14H11N4O2S.Na
Molecular Weight 322.318
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFAQUINOXALINE SODIUM

SMILES

[Na+].NC1=CC=C(C=C1)S(=O)(=O)[N-]C2=NC3=CC=CC=C3N=C2

InChI

InChIKey=WXUQBKOBXREBBX-UHFFFAOYSA-N
InChI=1S/C14H11N4O2S.Na/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;/q-1;+1

HIDE SMILES / InChI

Description
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

Curator's Comment: # At Merck, chemist Max Tishler and his associate John Weijlard in the 1930s

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Batcerial dihydrofolate synthetase
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Curative
POULTRYSULFA Soluble Powder

Approved Use

Acute 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

PubMed

TitleDatePubMed
The therapeutic effect of 16 antimicrobial agents on Cryptosporidium infection in mice.
1982 Apr
In vitro cultivation of Cryptosporidium parvum and screening for anticryptosporidial drugs.
1990 Aug
Inhibition of Pneumocystis carinii dihydropteroate synthetase by sulfa drugs.
1990 Jun
Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs.
1995 Aug
Monodrug efficacies of sulfonamides in prophylaxis for Pneumocystis carinii pneumonia.
1996 Apr
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.
1996 Dec
Identification of a class of sulfonamides highly active against dihydropteroate synthase form Toxoplasma gondii, Pneumocystis carinii, and Mycobacterium avium.
1996 Mar
Matrix solid-phase dispersion extraction and high-performance liquid chromatographic determination of residual sulfonamides in chicken.
2001 Dec 7
Comparison of ion-pairing and ion-suppressing liquid chromatographic methods for the determination of pyrimethamine and ormetoprim in chicken feed.
2002 Jul
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
In vitro susceptibility of Ornithobacterium rhinotracheale to several antimicrobial drugs.
2003 Apr-Jun
Detection limits of antimicrobials in ewe milk by delvotest photometric measurements.
2003 Feb
Validation of a confirmatory method for the determination of sulphonamides in muscle according to the European Union regulation 2002/657/EC.
2004 Apr 2
Determination of some sulfonamides and trimethoprim in chicken, fish muscle and eggs by liquid chromatography-tandem mass spectrometry.
2004 Apr-Jun
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
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
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
[Determination of 12 sulfonamides in cosmetics by ultra performance liquid chromatography].
2007 Mar
Determination of 10 sulfonamide residues in meat samples by liquid chromatography with ultraviolet detection.
2007 Mar-Apr
[Simultaneous determination of nine sulfonamide residues in milk using solid phase extraction and high performance liquid chromatography].
2007 Sep
History of the discovery of sulfaquinoxaline as a coccidiostat.
2008 Aug
Application of liquid-liquid-liquid microextraction and high-performance liquid-chromatography for the determination of sulfonamides in water.
2008 Mar 31
Use of experimental design and effective mobility calculations to develop a method for the determination of antimicrobials by capillary electrophoresis.
2008 Sep 15
A landmark contribution to poultry science--prophylactic control of coccidiosis in poultry.
2009 Apr
Determination of ten sulphonamides in egg by liquid chromatography-tandem mass spectrometry.
2009 Apr 1
Development and validation of a confirmatory method for the determination of sulphonamides in milk by liquid chromatography with diode array detection.
2009 Apr 1
On-line coupling of dynamic microwave-assisted extraction to solid-phase extraction for the determination of sulfonamide antibiotics in soil.
2009 Aug 26
Analytical method for simultaneous determination of pesticide and veterinary drug residues in milk by CE-MS.
2009 May
Analysis of sulfonamides in environmental water samples based on magnetic mixed hemimicelles solid-phase extraction coupled with HPLC-UV detection.
2009 Nov
Fast and selective extraction of sulfonamides from honey based on magnetic molecularly imprinted polymer.
2009 Nov 11
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
Rapid separation and highly sensitive detection methodology for sulfonamides in shrimp using a monolithic column coupled with BDD amperometric detection.
2009 Sep 15
Determination of sulfonamides in soil samples based on alumina-coated magnetite nanoparticles as adsorbents.
2010 Apr 30
Protein microarray: sensitive and effective immunodetection for drug residues.
2010 Feb 16
Comparison of several extraction techniques for multiclass analysis of veterinary drugs in eggs using ultra-high pressure liquid chromatography-tandem mass spectrometry.
2010 Feb 28
Studies on the extraction of sulfonamides from agricultural soils.
2010 May
Evaluation of the aquatic toxicity of two veterinary sulfonamides using five test organisms.
2010 Oct
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.
2010 Oct 1
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.
2010 Sep 15
Patents

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
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).
Name Type Language
SULFAQUINOXALINE SODIUM
Common Name English
SULFAQUINOXALINE SODIUM [GREEN BOOK]
Common Name English
SODIUM SULFAQUINOXALINE
Common Name English
BENZENESULFONAMIDE, 4-AMINO-N-2-QUINOXALINYL-, MONOSODIUM SALT
Common Name English
N1-(QUINOXALIN-2-YL)SULPHANILAMIDE SODIUM SALT
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C28394
Created by admin on Fri Dec 15 15:09:02 GMT 2023 , Edited by admin on Fri Dec 15 15:09:02 GMT 2023
Code System Code Type Description
FDA UNII
21223EPJ40
Created by admin on Fri Dec 15 15:09:02 GMT 2023 , Edited by admin on Fri Dec 15 15:09:02 GMT 2023
PRIMARY
DRUG BANK
DBSALT002218
Created by admin on Fri Dec 15 15:09:02 GMT 2023 , Edited by admin on Fri Dec 15 15:09:02 GMT 2023
PRIMARY
PUBCHEM
3693427
Created by admin on Fri Dec 15 15:09:02 GMT 2023 , Edited by admin on Fri Dec 15 15:09:02 GMT 2023
PRIMARY
EPA CompTox
DTXSID30914383
Created by admin on Fri Dec 15 15:09:02 GMT 2023 , Edited by admin on Fri Dec 15 15:09:02 GMT 2023
PRIMARY
ECHA (EC/EINECS)
213-526-2
Created by admin on Fri Dec 15 15:09:02 GMT 2023 , Edited by admin on Fri Dec 15 15:09:02 GMT 2023
PRIMARY
NCI_THESAURUS
C90992
Created by admin on Fri Dec 15 15:09:02 GMT 2023 , Edited by admin on Fri Dec 15 15:09:02 GMT 2023
PRIMARY
RXCUI
1306110
Created by admin on Fri Dec 15 15:09:02 GMT 2023 , Edited by admin on Fri Dec 15 15:09:02 GMT 2023
PRIMARY RxNorm
CAS
967-80-6
Created by admin on Fri Dec 15 15:09:02 GMT 2023 , Edited by admin on Fri Dec 15 15:09:02 GMT 2023
PRIMARY
SMS_ID
300000029176
Created by admin on Fri Dec 15 15:09:02 GMT 2023 , Edited by admin on Fri Dec 15 15:09:02 GMT 2023
PRIMARY
DAILYMED
21223EPJ40
Created by admin on Fri Dec 15 15:09:02 GMT 2023 , Edited by admin on Fri Dec 15 15:09:02 GMT 2023
PRIMARY