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)
Molecular Formula | C14H12N4O2S |
Molecular Weight | 300.336 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|---|
Target ID: Batcerial dihydrofolate synthetase Sources: http://www.kdqchem.com/pages/pro4-8.htm |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Unknown Approved UseUnknown |
|||
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 |
---|---|---|
In vitro cultivation of Cryptosporidium parvum and screening for anticryptosporidial drugs. | 1990 Aug |
|
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 |
|
Detection limits of antimicrobials in ewe milk by delvotest photometric measurements. | 2003 Feb |
|
Determination of 14C residue in eggs of laying hens administered orally with [14C] sulfaquinoxaline. | 2004 Jun |
|
Determination of sulfonamide residues in the tissues of food animals using automated precolumn derivatization and liquid chromatography with fluorescence detection. | 2004 Sep-Oct |
|
[Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry]. | 2005 Jul |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
[Determination of residual sulfonamides in meat by high performance liquid chromatography with solid-phase extraction]. | 2005 Nov |
|
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 |
|
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 |
|
[Determination of 12 sulfonamides in cosmetics by ultra performance liquid chromatography]. | 2007 Mar |
|
Validation of an analytical method to determine sulfamides in kidney by HPLC-DAD and PARAFAC2 with first-order derivative chromatograms. | 2007 Mar 28 |
|
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 |
|
On-line coupling of dynamic microwave-assisted extraction to solid-phase extraction for the determination of sulfonamide antibiotics in soil. | 2009 Aug 26 |
|
Analysis of sulfonamides in environmental water samples based on magnetic mixed hemimicelles solid-phase extraction coupled with HPLC-UV detection. | 2009 Nov |
|
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 |
|
Rapid separation and highly sensitive detection methodology for sulfonamides in shrimp using a monolithic column coupled with BDD amperometric detection. | 2009 Sep 15 |
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).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:06:36 GMT 2023
by
admin
on
Fri Dec 15 15:06:36 GMT 2023
|
Record UNII |
WNW8115TM9
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
CFR |
21 CFR 556.685
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
||
|
WHO-VATC |
QJ01EW16
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
||
|
WHO-VATC |
QP51AG53
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
||
|
CFR |
21 CFR 520.2325A
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
||
|
CFR |
21 CFR 520.2325
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
||
|
CFR |
21 CFR 558.586
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
||
|
CFR |
21 CFR 520.2218
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
||
|
WHO-VATC |
QP51AG03
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
||
|
EPA PESTICIDE CODE |
77901
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
||
|
NCI_THESAURUS |
C29739
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
||
|
CFR |
21 CFR 520.2325B
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
||
|
WHO-VATC |
QJ01EQ16
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
DTXSID8042424
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
PRIMARY | |||
|
CHEMBL1437847
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
PRIMARY | |||
|
SUB10725MIG
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
PRIMARY | |||
|
D013428
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
PRIMARY | |||
|
WNW8115TM9
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
PRIMARY | |||
|
SULFAQUINOXALINE
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
PRIMARY | |||
|
59-40-5
Created by
admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
|
PRIMARY | |||
|
WNW8115TM9
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
PRIMARY | |||
|
1306111
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
PRIMARY | RxNorm | ||
|
1635206
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
PRIMARY | |||
|
41805
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
PRIMARY | |||
|
5058
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
PRIMARY | |||
|
200-423-2
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
PRIMARY | |||
|
7440
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
PRIMARY | |||
|
100000083297
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
PRIMARY | |||
|
5338
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
PRIMARY | |||
|
DB11464
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
PRIMARY | |||
|
C76979
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
PRIMARY | |||
|
m10340
Created by
admin on Fri Dec 15 15:06:37 GMT 2023 , Edited by admin on Fri Dec 15 15:06:37 GMT 2023
|
PRIMARY | Merck Index |
Related Record | Type | Details | ||
---|---|---|---|---|
|
SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
MAJOR
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |