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 |
---|---|---|---|---|
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 |
---|---|---|
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 |
---|---|---|
Hydrogen bonding in sulfonamides. | 2001 Dec |
|
Determination of sulfamethazine and trimethoprim in liquid feed premixes by HPLC and diode array detection, with an analysis of the uncertainty of the analytical results. | 2001 Jul |
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The teratogenic risk of trimethoprim-sulfonamides: a population based case-control study. | 2001 Nov-Dec |
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Sulphonamide residues in eggs following drug administration via the drinking water. | 2002 Apr |
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A new, sensitive, and rapid spectrophotometric method for the determination of sulfa drugs. | 2002 Jul-Aug |
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IARC monographs, industry influence, and upgrading, downgrading, and under-grading chemicals: a personal point of view. International Agency for Research on Cancer. | 2002 Jul-Sep |
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Bioconcentration and elimination of sulfamethazine and its main metabolite in sturgeon (Acipenser schrenkii). | 2003 Dec 17 |
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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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Routine monitoring of antibiotics in water and wastewater with a radioimmunoassay technique. | 2004 Aug-Sep |
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Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions. | 2004 Jul-Aug |
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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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[Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry]. | 2005 Jul |
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Surface runoff and transport of sulfonamide antibiotics and tracers on manured grassland. | 2005 Jul-Aug |
|
European Proficiency testing of national reference laboratories for the confirmation of sulfonamide residues in muscle and milk. | 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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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 |
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
Sun Dec 18 20:49:56 UTC 2022
by
admin
on
Sun Dec 18 20:49:56 UTC 2022
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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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admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
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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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PRIMARY | |||
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683529
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PRIMARY | |||
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1068
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PRIMARY | |||
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M10317
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PRIMARY | Merck Index | ||
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SUB10699MIG
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PRIMARY | |||
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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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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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2502
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10178
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DTXSID6021290
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48U51W007F
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PRIMARY | |||
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1629000
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PRIMARY | |||
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5327
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PRIMARY |
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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METABOLITE -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |