Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C12H14N4O2S.H2O4S |
| Molecular Weight | 376.409 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=N1
InChI
InChIKey=SOHZBANIDAJXHD-UHFFFAOYSA-N
InChI=1S/C12H14N4O2S.H2O4S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11;1-5(2,3)4/h3-7H,13H2,1-2H3,(H,14,15,16);(H2,1,2,3,4)
| Molecular Formula | H2O4S |
| Molecular Weight | 98.078 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
DescriptionCurator'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
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) |
5.7 µM [IC50] | ||
Target ID: UniProt: B6KBG5 (Dihydropteroate synthase) |
5.7 µM [IC50] | ||
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| 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). |
|||
| 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). |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Arylamine N-acetyltransferase activities in human breast cancer tissues. | 2001 |
|
| Functional characterization of human N-acetyltransferase 2 (NAT2) single nucleotide polymorphisms. | 2001 Apr |
|
| The effect of hepatic microsomal cytochrome P450 monooxygenases on monensin-sulfadimidine interactions in broilers. | 2001 Feb |
|
| The teratogenic risk of trimethoprim-sulfonamides: a population based case-control study. | 2001 Nov-Dec |
|
| [Diagnosis of acetylation phenotype in the protection of production personnel]. | 2002 |
|
| Quantification of veterinary antibiotics (sulfonamides and trimethoprim) in animal manure by liquid chromatography-mass spectrometry. | 2002 Apr 5 |
|
| CYP3A4 induction by drugs: correlation between a pregnane X receptor reporter gene assay and CYP3A4 expression in human hepatocytes. | 2002 Jul |
|
| Determination of sulfonamide residues in eggs by liquid chromatography. | 2002 Jul-Aug |
|
| Functional genomics of C190T single nucleotide polymorphism in human N-acetyltransferase 2. | 2002 Jun |
|
| In vitro susceptibility of Ornithobacterium rhinotracheale to several antimicrobial drugs. | 2003 Apr-Jun |
|
| A clean and rapid liquid chromatographic technique for sulfamethazine monitoring in pork tissues without using organic solvents. | 2003 Aug |
|
| A sensitive method for detection of sulfamethazine and N4-acetylsulfamethazine residues in environmental samples using solid phase immunoextraction coupled with MALDI-TOF MS. | 2003 Aug 27 |
|
| 3-Aminophenol as a novel coupling agent for the spectrophotometric determination of sulfonamide derivatives. | 2003 Dec |
|
| Pharmacokinetics of a novel N-methyl-D-aspartate receptor antagonist (SM-18400): identification of an N-acetylated metabolite and pre-clinical assessment of N-acetylation polymorphism. | 2003 Jan-Mar |
|
| Preliminary evaluation of a lateral flow immunoassay device for screening urine samples for the presence of sulphamethazine. | 2003 Jul |
|
| Studies on the efficacy of toltrazuril, diclazuril and sulphadimidine against artificial infections with Isospora suis in piglets. | 2003 Jul |
|
| Novel sulfamethazine ligand used for one-step purification of immunoglobulin G from human plasma. | 2003 Jul 25 |
|
| Xenobiotic inducible regions of the human arylamine N-acetyltransferase 1 and 2 genes. | 2003 Mar 20 |
|
| Separation and determination of the antitumor drug piritrexim by molecularly imprinted microspheres in high-performance liquid chromatography. | 2003 Sep |
|
| Validation of a confirmatory method for the determination of sulphonamides in muscle according to the European Union regulation 2002/657/EC. | 2004 Apr 2 |
|
| Chemometric and derivative methods as flexible spectrophotometric approaches for dissolution and assaying tests in multicomponent tablets. | 2004 Aug |
|
| Routine monitoring of antibiotics in water and wastewater with a radioimmunoassay technique. | 2004 Aug-Sep |
|
| Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions. | 2004 Jul-Aug |
|
| [Determination of the residues of five sulfa drugs in eel by HPLC]. | 2004 Mar |
|
| Administration of and withdrawal periods for sulphadimidine solution. | 2004 Sep 18 |
|
| Determination of sulfonamide residues in the tissues of food animals using automated precolumn derivatization and liquid chromatography with fluorescence detection. | 2004 Sep-Oct |
|
| Effect of agricultural antibiotics on the persistence and transformation of 17beta-estradiol in a Sequatchie loam. | 2005 |
|
| Microbial inhibition by pharmaceutical antibiotics in different soils--dose-response relations determined with the iron(III) reduction test. | 2005 Apr |
|
| Different behavior of tetracyclines and sulfonamides in sandy soils after repeated fertilization with liquid manure. | 2005 Apr |
|
| Proteomic analysis using an unfinished bacterial genome: the effects of subminimum inhibitory concentrations of antibiotics on Mannheimia haemolytica virulence factor expression. | 2005 Dec |
|
| [Effect of sulphamethazine on the gene expression of FRTL-5 cells]. | 2005 Jan |
|
| [Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry]. | 2005 Jul |
|
| Photocatalytic oxidation of sulfamethazine. | 2005 Jul |
|
| Evaluating the biodegradability of sulfamethazine, sulfamethoxazole, sulfathiazole, and trimethoprim at different stages of sewage treatment. | 2005 Jun |
|
| Cross-coupling of sulfonamide antimicrobial agents with model humic constituents. | 2005 Jun 15 |
|
| Effects of mannan oligosaccharide and an antimicrobial product in nursery diets on performance of pigs reared on three different farms. | 2005 Nov |
|
| Monitoring of five sulfonamide antibacterial residues in milk by in-tube solid-phase microextraction coupled to high-performance liquid chromatography. | 2005 Nov 2 |
|
| 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 |
|
| 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 |
|
| Dispersive solid-phase extraction for the determination of sulfonamides in chicken muscle by liquid chromatography. | 2005 Sep 16 |
|
| 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 |
|
| 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
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
Fri Dec 15 16:31:50 GMT 2023
by
admin
on
Fri Dec 15 16:31:50 GMT 2023
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| Record UNII |
5J847L84W0
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| Record Status |
Validated (UNII)
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| Record Version |
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Download
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English |
| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29739
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24540-76-9
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21393658
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5J847L84W0
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C87217
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