U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H14N4O2S
Molecular Weight 278.33
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFAMETHAZINE

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)

HIDE SMILES / InChI

Molecular Formula C12H14N4O2S
Molecular Weight 278.33
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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).

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
[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
Sex-dependent pharmacokinetics of S(-)-hydroxyhexamide, a pharmacologically active metabolite of acetohexamide, in rats.
2002 Dec
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
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
Functional genomics of C190T single nucleotide polymorphism in human N-acetyltransferase 2.
2002 Jun
Rapid and sensitive screening of sulfamethazine in porcine urine with an enzyme-linked immunosorbent assay and a field-portable immunofiltration assay.
2002 May
Identification of the 'wrong' active pharmaceutical ingredient in a counterfeit Halfan drug product using accurate mass electrospray ionisation mass spectrometry, accurate mass tandem mass spectrometry and liquid chromatography/mass spectrometry.
2003
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
[Determination of sulfamethazine and sulfamethoxazole in muscle of chicken by high performance liquid chromatography].
2003 Nov
Activities of drug metabolizing enzymes in bovine colon epithelial cell cultures.
2003 Nov
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
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
Possible association between different congenital abnormalities and use of different sulfonamides during pregnancy.
2004 Jun
[Determination of the residues of five sulfa drugs in eel by HPLC].
2004 Mar
Quantitative assessment of the reliability of identification by high-performance liquid chromatography-mass spectrometry.
2004 Mar 26
Prediction of chronic liver diseases on the basis of the N-acetyltransferase 2 phenotype.
2004 Mar-Apr
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
Test-plot studies on runoff of sulfonamides from manured soils after sprinkler irrigation.
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
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
Attenuation of gonadal response to photostimulation following ablation of neurons in the lateral septal organ of chicks.
2005 Jan 15
[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
Surface runoff and transport of sulfonamide antibiotics and tracers on manured grassland.
2005 Jul-Aug
Evaluating the biodegradability of sulfamethazine, sulfamethoxazole, sulfathiazole, and trimethoprim at different stages of sewage treatment.
2005 Jun
Use of sulfonamides in layers in Kampala district, Uganda and sulfonamide residues in commercial eggs.
2005 Mar
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
Preparation and evaluation of uniform-sized molecularly imprinted polymer beads used for the separation of sulfamethazine.
2005 Sep
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

In Vivo Use Guide
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
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:33:22 UTC 2019
Edited
by admin
on Mon Oct 21 20:33:22 UTC 2019
Record UNII
48U51W007F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SULFAMETHAZINE
GREEN BOOK   HSDB   MI   USP   USP-RS   VANDF  
Common Name English
SULFAMETHAZINE [USP-RS]
Common Name English
SULFAMETHAZINE [VANDF]
Common Name English
SULFADIMIDINUM [WHO-IP LATIN]
Common Name English
4,6-DIMETHYL-2-SULFANILAMIDOPYRIMIDINE
Systematic Name English
BENZENESULFONAMIDE, 4-AMINO-N-(4,6-DIMETHYL-2-PYRIMIDINYL)-
Systematic Name English
SULFAMETHAZINE [IARC]
Common Name English
SULFADIMETHYLPYRIMIDINE
Common Name English
SULFOSE COMPONENT SULFAMETHAZINE
Common Name English
SULFADIMIDINE [INN]
Common Name English
SULFAMETHAZINE COMPONENT OF TERFONYL
Common Name English
SULFADIMIDINE [WHO-IP]
Common Name English
LANTRISUL COMPONENT SULFAMETHAZINE
Common Name English
SULFADIMERAZINE
Common Name English
NEOTRIZINE COMPONENT SULFAMETHAZINE
Common Name English
SULFADIMIDINE [EP]
Common Name English
N(SUP 1)-(4,6-DIMETHYL-2-PYRIMIDINYL)SULFANILAMIDE
Systematic Name English
NSC-67457
Code English
SULFAMETHAZINE COMPONENT OF NEOTRIZINE
Common Name English
TRIPLE SULFOID COMPONENT SULFAMETHAZINE
Common Name English
SULFAMEZATHINE
Common Name English
BN-2409
Code English
SULFAMETHAZINE COMPONENT OF LANTRISUL
Common Name English
SULFAMETHAZINE [HSDB]
Common Name English
NSC-683529
Code English
4-AMINO-N-(4,6-DIMETHYL-2-PYRIMIDINYL)BENZENESULFONAMIDE
Systematic Name English
SULFAMETHAZINE COMPONENT OF SULFALOID
Common Name English
SULFADIMIDINE
EP   INN   MART.   WHO-DD   WHO-IP  
INN  
Official Name English
SULFAMETHAZINE [MI]
Common Name English
SULFALOID COMPONENT SULFAMETHAZINE
Common Name English
SULFAMETHAZINE COMPONENT OF SULFOSE
Common Name English
SULFAMIDINE
Common Name English
SULFADIMIDINE [WHO-DD]
Common Name English
TERFONYL COMPONENT SULFAMETHAZINE
Common Name English
SULFAMETHAZINE [USP]
Common Name English
SULFAMETHAZINE [GREEN BOOK]
Common Name English
SULFAMETHAZINE COMPONENT OF TRIPLE SULFOID
Common Name English
SULFADIMIDINE [MART.]
Common Name English
Classification Tree Code System Code
WHO-VATC QP51AG51
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
CFR 21 CFR 520.445
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
WHO-VATC QJ01EW03
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
CFR 21 CFR 520.2218
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
CFR 21 CFR 520.2261A
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
WHO-VATC QP51AG01
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
NCI_THESAURUS C29739
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
CFR 21 CFR 558.630
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
WHO-VATC QG51AG02
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
CFR 21 CFR 520.2260A
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
WHO-VATC QJ01EQ03
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
CFR 21 CFR 520.2261B
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
CFR 21 CFR 558.145
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
WHO-ATC J01EE05
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
CFR 21 CFR 558.140
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
IARC Sulfamethazine
WHO-VATC QG51AG01
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
WHO-VATC QG51AG03
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
LIVERTOX 909
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
CFR 21 CFR 556.670
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
CFR 21 CFR 522.2260
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
CFR 21 CFR 558.145
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
WHO-VATC QJ51RC04
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
CFR 21 CFR 520.2260B
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
WHO-ATC J01EB03
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
CFR 21 CFR 558.140
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
CFR 21 CFR 520.2260
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
CFR 21 CFR 520.2260C
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
Code System Code Type Description
CAS
57-68-1
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
PRIMARY
INN
1068
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
PRIMARY
MERCK INDEX
M10317
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
PRIMARY Merck Index
EVMPD
SUB10699MIG
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
PRIMARY
MESH
C043086
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
SULFAMETHAZINE
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
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.
MESH
D013418
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
PRIMARY
HSDB
57-68-1
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
PRIMARY
NCI_THESAURUS
C61960
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
PRIMARY
WIKIPEDIA
SULFADIMIDINE
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
PRIMARY
ChEMBL
CHEMBL446
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
PRIMARY
DRUG BANK
DB01582
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-346-4
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
PRIMARY
RXCUI
10178
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
PRIMARY RxNorm
EPA CompTox
57-68-1
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
PRIMARY
PUBCHEM
5327
Created by admin on Mon Oct 21 20:33:23 UTC 2019 , Edited by admin on Mon Oct 21 20:33:23 UTC 2019
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY