U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of SULFAQUINOXALINE

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)

HIDE SMILES / InChI

Molecular Formula C14H12N4O2S
Molecular Weight 300.336
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown
Curative
POULTRYSULFA Soluble Powder

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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).
Substance Class Chemical
Record UNII
WNW8115TM9
Record Status Validated (UNII)
Record Version