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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
Monodrug efficacies of sulfonamides in prophylaxis for Pneumocystis carinii pneumonia.
1996 Apr
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 14C residue in eggs of laying hens administered orally with [14C] sulfaquinoxaline.
2004 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 residues of sulphonamide in eggs and laying hens.
2007 Jul
History of the discovery of sulfaquinoxaline as a coccidiostat.
2008 Aug
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
Rapid separation and highly sensitive detection methodology for sulfonamides in shrimp using a monolithic column coupled with BDD amperometric detection.
2009 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
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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
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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
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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
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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
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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
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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
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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
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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
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