Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C12H13N4O2S.Na |
| Molecular Weight | 300.312 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CC1=CC(C)=NC([N-]S(=O)(=O)C2=CC=C(N)C=C2)=N1
InChI
InChIKey=NGIVTUVVBWOTNT-UHFFFAOYSA-N
InChI=1S/C12H13N4O2S.Na/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;/q-1;+1
| 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 |
| Molecular Formula | Na |
| Molecular Weight | 22.9898 |
| Charge | 1 |
| 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 |
|---|---|---|
| Functional characterization of human N-acetyltransferase 2 (NAT2) single nucleotide polymorphisms. | 2001 Apr |
|
| High-performance liquid chromatographic procedure for routine residue monitoring of seven sulfonamides in milk. | 2001 Dec |
|
| Synthesis and anti-HIV activity of 4-[(1,2-dihydro-2-oxo-3H-indol-3-ylidene) amino]-N(4,6-dimethyl-2-pyrimidinyl)-benzene sulfonamide and its derivatives. | 2001 Dec |
|
| Matrix solid-phase dispersion extraction and high-performance liquid chromatographic determination of residual sulfonamides in chicken. | 2001 Dec 7 |
|
| Spermidine/spermine n(1)-acetyltransferase catalyzes amantadine acetylation. | 2001 May |
|
| 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 |
|
| Sulphonamide residues in eggs following drug administration via the drinking water. | 2002 Apr |
|
| [Comparative study of combined local treatment (sulfadimidine, metronidazole and nystatin) and the standard monotherapy in uncomplicated bacterial vaginosis]. | 2002 Dec 22 |
|
| Liquid chromatographic determination of multiple sulfonamides, nitrofurans, and chloramphenicol residues in pasteurized milk. | 2002 Jan-Feb |
|
| CYP3A4 induction by drugs: correlation between a pregnane X receptor reporter gene assay and CYP3A4 expression in human hepatocytes. | 2002 Jul |
|
| A new, sensitive, and rapid spectrophotometric method for the determination of sulfa drugs. | 2002 Jul-Aug |
|
| Iminodibenzyl as a novel coupling agent for the spectrophotometric determination of sulfonamide derivatives. | 2002 Mar |
|
| Rapid and sensitive screening of sulfamethazine in porcine urine with an enzyme-linked immunosorbent assay and a field-portable immunofiltration assay. | 2002 May |
|
| In vitro susceptibility of Ornithobacterium rhinotracheale to several antimicrobial drugs. | 2003 Apr-Jun |
|
| 3-Aminophenol as a novel coupling agent for the spectrophotometric determination of sulfonamide derivatives. | 2003 Dec |
|
| Bioconcentration and elimination of sulfamethazine and its main metabolite in sturgeon (Acipenser schrenkii). | 2003 Dec 17 |
|
| Determination of acidic pharmaceuticals, antibiotics and ivermectin in river sediment using liquid chromatography-tandem mass spectrometry. | 2003 Dec 22 |
|
| Interaction of ibuprofen and probenecid with drug metabolizing enzyme phenotyping procedures using caffeine as the probe drug. | 2003 Feb |
|
| Studies on the efficacy of toltrazuril, diclazuril and sulphadimidine against artificial infections with Isospora suis in piglets. | 2003 Jul |
|
| Generation and functional characterization of arylamine N-acetyltransferase Nat1/Nat2 double-knockout mice. | 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 |
|
| Prevalence and control of bovine cryptosporidiosis in German dairy herds. | 2003 Mar 25 |
|
| Antibiotics in dust originating from a pig-fattening farm: a new source of health hazard for farmers? | 2003 Oct |
|
| Quartz crystal biosensor for real-time monitoring of molecular recognition between protein and small molecular medicinal agents. | 2003 Oct 30 |
|
| Separation and determination of the antitumor drug piritrexim by molecularly imprinted microspheres in high-performance liquid chromatography. | 2003 Sep |
|
| [Determination of the hereditary and constitutive predisposition to peritoneal commissures]. | 2004 |
|
| 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 |
|
| 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 |
|
| Automated microarray system for the simultaneous detection of antibiotics in milk. | 2004 Feb 1 |
|
| Antimicrobial use in the treatment of calf diarrhea. | 2004 Jan-Feb |
|
| Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions. | 2004 Jul-Aug |
|
| Test-plot studies on runoff of sulfonamides from manured soils after sprinkler irrigation. | 2005 Apr |
|
| 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 |
|
| Eukaryotic arylamine N-acetyltransferase. Investigation of substrate specificity by high-throughput screening. | 2005 Jan 15 |
|
| Cross-coupling of sulfonamide antimicrobial agents with model humic constituents. | 2005 Jun 15 |
|
| European Proficiency testing of national reference laboratories for the confirmation of sulfonamide residues in muscle and milk. | 2005 Mar |
|
| 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 |
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
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admin
on
Edited
Fri Dec 16 16:00:22 UTC 2022
by
admin
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Fri Dec 16 16:00:22 UTC 2022
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| Record UNII |
7Z13P9Q95C
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| Record Status |
Validated (UNII)
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| Record Version |
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CFR |
21 CFR 520.2261
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NCI_THESAURUS |
C29739
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13456556
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1364374
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7Z13P9Q95C
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1981-58-4
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7Z13P9Q95C
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M10317
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DTXSID70890551
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DBSALT002199
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C84184
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SULFAMETHAZINE SODIUM
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admin on Fri Dec 16 16:00:22 UTC 2022 , Edited by admin on Fri Dec 16 16:00:22 UTC 2022
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PRIMARY | Description: A white or creamy white, crystalline powder; odourless or almost odourless. Solubility: Soluble in 2.5 parts of water and in 60 parts of ethanol (~750 g/l) TS. Category: Antibacterial drug. Storage: Sulfadimidine sodium should be kept in a well-closed container, protected from light. Additional information: Even in the absence of light, Sulfadimidine sodium is gradually degraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures. Definition: Sulfadimidine sodium contains not less than 98.0% and not more than 101.0% of C12H13N4NaO2S, calculated with reference to the dried substance. | ||
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217-840-0
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |