Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H14N4O2S |
Molecular Weight | 278.33 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=N1
InChI
InChIKey=ASWVTGNCAZCNNR-UHFFFAOYSA-N
InChI=1S/C12H14N4O2S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11/h3-7H,13H2,1-2H3,(H,14,15,16)
Molecular Formula | C12H14N4O2S |
Molecular Weight | 278.33 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.drugbank.ca/drugs/DB01582Curator's Comment: Description was created based on several sources, including
https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm061367.pdf | https://www.drugs.com/vet/sulfamethazine-25-solution-can.html
Sources: https://www.drugbank.ca/drugs/DB01582
Curator's Comment: Description was created based on several sources, including
https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm061367.pdf | https://www.drugs.com/vet/sulfamethazine-25-solution-can.html
Sulfamethazine is a sulfonamide used to treat a variety of bacterial diseases in animals. It inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for binding to dihydropteroate synthetase (dihydrofolate synthetase).
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: UniProt: B6KBG5 (Dihydropteroate synthase) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2298911 |
5.7 µM [IC50] | ||
Target ID: UniProt: B6KBG5 (Dihydropteroate synthase) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2298911 |
5.7 µM [IC50] | ||
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | SULMET Approved UseINDICATIONS FOR USE
Turkeys
For treatment and control of the following diseases caused by the following pathogenic organisms susceptible to sulfamethazine. In turkeys for control of coccidiosis (Eimeria meleagrimitis, Eimeria adenoeides). Medicate for 2 days, then reduce amount of medication to one-half for 4 additional days.
Chickens
For treatment and control of the following diseases caused by the following pathogenic organisms susceptible to sulfamethazine. In chickens for control of infectious coryza (Avibacterium paragallinarum), coccidiosis (Eimeria tenella, Eimeria necatrix), acute fowl cholera (Pasteurella multocida), and pullorum disease (Salmonella Pullorum). Medicate as follows: Infectious coryza, medicate for 2 consecutive days; acute fowl cholera and pullorum disease, medicate for 6 consecutive days; coccidiosis, medicate for 2 days, then reduce amount of medication to one-half for 4 additional days.
Cattle (beef and nonlactating dairy)
For treatment and control of the following diseases caused by the following pathogenic organisms susceptible to sulfamethazine. Treatment of bacterial pneumonia and bovine respiratory disease complex (shipping fever complex) (Pasteurella species), colibacillosis (bacterial scours) (Escherichia coli), necrotic pododermatitis (foot rot) (Fusobacterium necrophorum), calf diphtheria (Fusobacterium necrophorum), acute metritis (Streptococcus species), and acute mastitis in beef cattle (Streptococcus species).
Swine
For treatment and control of the following diseases caused by the following pathogenic organisms susceptible to sulfamethazine. For treatment and control of diseases caused by organisms to sulfamethazine. Treatment of porcine colibacillosis (bacterial scours) (Escherichia coli), and bacterial pneumonia (Pasteurella species). |
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Curative | SULMET Approved UseINDICATIONS FOR USE
Turkeys
For treatment and control of the following diseases caused by the following pathogenic organisms susceptible to sulfamethazine. In turkeys for control of coccidiosis (Eimeria meleagrimitis, Eimeria adenoeides). Medicate for 2 days, then reduce amount of medication to one-half for 4 additional days.
Chickens
For treatment and control of the following diseases caused by the following pathogenic organisms susceptible to sulfamethazine. In chickens for control of infectious coryza (Avibacterium paragallinarum), coccidiosis (Eimeria tenella, Eimeria necatrix), acute fowl cholera (Pasteurella multocida), and pullorum disease (Salmonella Pullorum). Medicate as follows: Infectious coryza, medicate for 2 consecutive days; acute fowl cholera and pullorum disease, medicate for 6 consecutive days; coccidiosis, medicate for 2 days, then reduce amount of medication to one-half for 4 additional days.
Cattle (beef and nonlactating dairy)
For treatment and control of the following diseases caused by the following pathogenic organisms susceptible to sulfamethazine. Treatment of bacterial pneumonia and bovine respiratory disease complex (shipping fever complex) (Pasteurella species), colibacillosis (bacterial scours) (Escherichia coli), necrotic pododermatitis (foot rot) (Fusobacterium necrophorum), calf diphtheria (Fusobacterium necrophorum), acute metritis (Streptococcus species), and acute mastitis in beef cattle (Streptococcus species).
Swine
For treatment and control of the following diseases caused by the following pathogenic organisms susceptible to sulfamethazine. For treatment and control of diseases caused by organisms to sulfamethazine. Treatment of porcine colibacillosis (bacterial scours) (Escherichia coli), and bacterial pneumonia (Pasteurella species). |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/ |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [Ki 476 uM] |
PubMed
Title | Date | PubMed |
---|---|---|
[Rheological and biopharmaceutical investigation of polymer drug delivery systems]. | 2003 |
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3-Aminophenol as a novel coupling agent for the spectrophotometric determination of sulfonamide derivatives. | 2003 Dec |
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Bioconcentration and elimination of sulfamethazine and its main metabolite in sturgeon (Acipenser schrenkii). | 2003 Dec 17 |
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Determination of acidic pharmaceuticals, antibiotics and ivermectin in river sediment using liquid chromatography-tandem mass spectrometry. | 2003 Dec 22 |
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[Determination of sulfamethazine and sulfamethoxazole in muscle of chicken by high performance liquid chromatography]. | 2003 Nov |
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[Determination of the hereditary and constitutive predisposition to peritoneal commissures]. | 2004 |
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Quantitative determination of trace concentrations of tetracycline and sulfonamide antibiotics in surface water using solid-phase extraction and liquid chromatography/ion trap tandem mass spectrometry. | 2004 |
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Validation of a confirmatory method for the determination of sulphonamides in muscle according to the European Union regulation 2002/657/EC. | 2004 Apr 2 |
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Antibiotic residues in edible tissues and antibiotic resistance of faecal Escherichia coli in pigs from Portugal. | 2004 Aug |
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Chemometric and derivative methods as flexible spectrophotometric approaches for dissolution and assaying tests in multicomponent tablets. | 2004 Aug |
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Quantitative analysis of twelve sulfonamides in honey after acidic hydrolysis by high-performance liquid chromatography with post-column derivatization and fluorescence detection. | 2004 Aug 20 |
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Routine monitoring of antibiotics in water and wastewater with a radioimmunoassay technique. | 2004 Aug-Sep |
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Sulfamethazine advances puberty in male chicks by effecting a rapid increase in gonadotropins. | 2004 Feb |
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Automated microarray system for the simultaneous detection of antibiotics in milk. | 2004 Feb 1 |
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[Effect of starvation and acetone on the enzyme systems of biotransformation and toxicity of xenobiotics--CYP2E1 substrates in rats]. | 2004 Jan-Feb |
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Antimicrobial use in the treatment of calf diarrhea. | 2004 Jan-Feb |
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Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions. | 2004 Jul-Aug |
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Possible association between different congenital abnormalities and use of different sulfonamides during pregnancy. | 2004 Jun |
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[Determination of the residues of five sulfa drugs in eel by HPLC]. | 2004 Mar |
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Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers. | 2004 Mar |
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Quantitative assessment of the reliability of identification by high-performance liquid chromatography-mass spectrometry. | 2004 Mar 26 |
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Prediction of chronic liver diseases on the basis of the N-acetyltransferase 2 phenotype. | 2004 Mar-Apr |
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Administration of and withdrawal periods for sulphadimidine solution. | 2004 Sep 18 |
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Determination of sulfonamide residues in the tissues of food animals using automated precolumn derivatization and liquid chromatography with fluorescence detection. | 2004 Sep-Oct |
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Effect of agricultural antibiotics on the persistence and transformation of 17beta-estradiol in a Sequatchie loam. | 2005 |
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Microbial inhibition by pharmaceutical antibiotics in different soils--dose-response relations determined with the iron(III) reduction test. | 2005 Apr |
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Different behavior of tetracyclines and sulfonamides in sandy soils after repeated fertilization with liquid manure. | 2005 Apr |
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Test-plot studies on runoff of sulfonamides from manured soils after sprinkler irrigation. | 2005 Apr |
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Proteomic analysis using an unfinished bacterial genome: the effects of subminimum inhibitory concentrations of antibiotics on Mannheimia haemolytica virulence factor expression. | 2005 Dec |
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[Effect of sulphamethazine on the gene expression of FRTL-5 cells]. | 2005 Jan |
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Effects of sub-minimum inhibitory concentration antibiotic levels and temperature on growth kinetics and outer membrane protein expression in Mannheimia haemolytica and Haemophilus somnus. | 2005 Jan |
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Eukaryotic arylamine N-acetyltransferase. Investigation of substrate specificity by high-throughput screening. | 2005 Jan 15 |
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Attenuation of gonadal response to photostimulation following ablation of neurons in the lateral septal organ of chicks. | 2005 Jan 15 |
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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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Photocatalytic oxidation of sulfamethazine. | 2005 Jul |
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Surface runoff and transport of sulfonamide antibiotics and tracers on manured grassland. | 2005 Jul-Aug |
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Evaluating the biodegradability of sulfamethazine, sulfamethoxazole, sulfathiazole, and trimethoprim at different stages of sewage treatment. | 2005 Jun |
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Cross-coupling of sulfonamide antimicrobial agents with model humic constituents. | 2005 Jun 15 |
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European Proficiency testing of national reference laboratories for the confirmation of sulfonamide residues in muscle and milk. | 2005 Mar |
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Use of sulfonamides in layers in Kampala district, Uganda and sulfonamide residues in commercial eggs. | 2005 Mar |
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Triplet-sensitized photodegradation of sulfa drugs containing six-membered heterocyclic groups: identification of an SO2 extrusion photoproduct. | 2005 May 15 |
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Confirmation of sulfamethazine, sulfathiazole, and sulfadimethoxine residues in condensed milk and soft-cheese products by liquid chromatography/tandem mass spectrometry. | 2005 May-Jun |
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Effects of mannan oligosaccharide and an antimicrobial product in nursery diets on performance of pigs reared on three different farms. | 2005 Nov |
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Monitoring of five sulfonamide antibacterial residues in milk by in-tube solid-phase microextraction coupled to high-performance liquid chromatography. | 2005 Nov 2 |
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Development of a physiologic-based pharmacokinetic model for estimating sulfamethazine concentrations in swine and application to prediction of violative residues in edible tissues. | 2005 Oct |
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Expression of cytochromes P450 and glutathione S-transferases in human prostate, and the potential for activation of heterocyclic amine carcinogens via acetyl-coA-, PAPS- and ATP-dependent pathways. | 2005 Oct 20 |
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Preparation and evaluation of uniform-sized molecularly imprinted polymer beads used for the separation of sulfamethazine. | 2005 Sep |
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Dispersive solid-phase extraction for the determination of sulfonamides in chicken muscle by liquid chromatography. | 2005 Sep 16 |
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A method for the quantification of low concentration sulfamethazine residues in milk based on molecularly imprinted clean-up and surface preconcentration at a Nafion-modified glassy carbon electrode. | 2006 Feb 13 |
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Occurrence of antibiotics in wastewater treatment facilities in Wisconsin, USA. | 2006 May 15 |
Patents
Sample Use Guides
Administer in drinking water to provide: Chickens 58 to 85 milligrams of sulfamethazine sodium per pound of body weight per day; turkeys 50 to 124 milligrams of sulfamethazine sodium per pound of body weight per day; depending upon the dosage, age, and class of chickens or turkeys, ambient temperature, and other factors. Administer to cattle and swine in drinking water, or as a drench, to provide 108 milligrams of sulfamethazine sodium per pound of body weight on the first day and 54 milligrams of sulfamethazine sodium per pound of body weight per day on the second, third, and fourth
days of administration.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10737648
Curator's Comment: Minimum inhibitory concentrations (MICs) for antimicrobial agents including sulfamethazine were determined for 1570 bacterial isolates from turkey poults from eight geographic locations (1204 Escherichia coli, 231 other enteric gram-negative bacilli [including Citrobacter spp., Enterobacter spp., Klebsiella spp., Proteus spp., and Salmonella spp.], 31 Pseudomonas spp., 18 coagulase-positive staphylococci, 26 coagulase-negative staphylococci, and 55 streptococci and enterococci)
Unknown
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 09:30:35 GMT 2025
by
admin
on
Wed Apr 02 09:30:35 GMT 2025
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Record UNII |
48U51W007F
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QP51AG51
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CFR |
21 CFR 520.445
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WHO-VATC |
QJ01EW03
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CFR |
21 CFR 520.2218
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CFR |
21 CFR 520.2261A
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WHO-VATC |
QP51AG01
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NCI_THESAURUS |
C29739
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CFR |
21 CFR 558.630
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WHO-VATC |
QG51AG02
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CFR |
21 CFR 520.2260A
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WHO-VATC |
QJ01EQ03
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CFR |
21 CFR 520.2261B
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CFR |
21 CFR 558.145
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WHO-ATC |
J01EE05
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CFR |
21 CFR 558.140
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IARC | Sulfamethazine | ||
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WHO-VATC |
QG51AG01
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WHO-VATC |
QG51AG03
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LIVERTOX |
909
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CFR |
21 CFR 556.670
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CFR |
21 CFR 522.2260
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CFR |
21 CFR 558.145
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WHO-VATC |
QJ51RC04
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CFR |
21 CFR 520.2260B
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WHO-ATC |
J01EB03
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CFR |
21 CFR 558.140
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CFR |
21 CFR 520.2260
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CFR |
21 CFR 520.2260C
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Code System | Code | Type | Description | ||
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57-68-1
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683529
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1068
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m10317
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SUB10699MIG
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C043086
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SULFAMETHAZINE
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PRIMARY | Description: A white or creamy white, crystalline powder; odourless or almost odourless. Solubility: Very slightly soluble in water; slightly soluble in ethanol (~750 g/l) TS; soluble in acetone R; practically insoluble in ether R. Category: Antibacterial drug. Storage: Sulfadimidine should be kept in a well-closed container, protected from light. Definition: Sulfadimidine contains not less than 99.0% and not more than 100.5% of C12H14N4O2S, calculated with reference to the dried substance. | ||
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100000089790
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48U51W007F
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D013418
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4157
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C61960
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SULFADIMIDINE
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CHEMBL446
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67457
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DB01582
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102265
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200-346-4
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10178
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DTXSID6021290
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48U51W007F
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1629000
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5327
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
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