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

Details

Stereochemistry ACHIRAL
Molecular Formula C12H14N4O2S
Molecular Weight 278.3317
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFAMETHAZINE

SMILES

Cc1cc(C)nc(n1)NS(=O)(=O)c2ccc(cc2)N

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

Description
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).

CNS Activity

Curator's Comment:: Sulfamethazine, a lipid-soluble, and poorly ionized drug of low molecular weight has been found to penetrate the blood-brain barrier differently in various species of animals and at different stages of brain development

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
SULMET

Approved Use

INDICATIONS 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 Use

INDICATIONS 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).
Doses

Doses

DosePopulationAdverse events​
40 mg/kg single, oral
Highest studied dose
Dose: 40 mg/kg
Route: oral
Route: single
Dose: 40 mg/kg
Sources:
healthy
n = 5
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes [Ki 476 uM]
PubMed

PubMed

TitleDatePubMed
Arylamine N-acetyltransferase activities in human breast cancer tissues.
2001
Molecular characterisation of aureocin A70, a multi-peptide bacteriocin isolated from Staphylococcus aureus.
2001 Aug 31
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
Determining the procedure for routine residue monitoring of sulfamethazine in edible animal tissues.
2001 Jun
Determination of selected sulfonamide antibiotics and trimethoprim in manure by electrospray and atmospheric pressure chemical ionization tandem mass spectrometry.
2002
Sulphonamide residues in eggs following drug administration via the drinking water.
2002 Apr
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
Use of optical biosensor technology to study immunological cross-reactivity between different sulfonamide drugs.
2002 Jan 15
[Rheological and biopharmaceutical investigation of polymer drug delivery systems].
2003
Determination of acidic pharmaceuticals, antibiotics and ivermectin in river sediment using liquid chromatography-tandem mass spectrometry.
2003 Dec 22
Preliminary evaluation of a lateral flow immunoassay device for screening urine samples for the presence of sulphamethazine.
2003 Jul
Separation and determination of the antitumor drug piritrexim by molecularly imprinted microspheres in high-performance liquid chromatography.
2003 Sep
Generation of group-specific antibodies against sulfonamides.
2003 Sep 24
[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
Antibiotic residues in edible tissues and antibiotic resistance of faecal Escherichia coli in pigs from Portugal.
2004 Aug
Sulfamethazine advances puberty in male chicks by effecting a rapid increase in gonadotropins.
2004 Feb
[Effect of starvation and acetone on the enzyme systems of biotransformation and toxicity of xenobiotics--CYP2E1 substrates in rats].
2004 Jan-Feb
Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers.
2004 Mar
Eukaryotic arylamine N-acetyltransferase. Investigation of substrate specificity by high-throughput screening.
2005 Jan 15
Surface runoff and transport of sulfonamide antibiotics and tracers on manured grassland.
2005 Jul-Aug
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
Triplet-sensitized photodegradation of sulfa drugs containing six-membered heterocyclic groups: identification of an SO2 extrusion photoproduct.
2005 May 15
Confirmation of sulfamethazine, sulfathiazole, and sulfadimethoxine residues in condensed milk and soft-cheese products by liquid chromatography/tandem mass spectrometry.
2005 May-Jun
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
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
Name Type Language
SULFAMETHAZINE
GREEN BOOK   HSDB   MI   USP   USP-RS   VANDF  
Common Name English
SULFAMETHAZINE [USP-RS]
Common Name English
SULFADIMIDINE [EP MONOGRAPH]
Common Name English
SULFAMETHAZINE [VANDF]
Common Name English
SULFADIMIDINUM [WHO-IP LATIN]
Common Name English
4,6-DIMETHYL-2-SULFANILAMIDOPYRIMIDINE
Systematic Name English
TRISULFAPYRIMIDINES (SULFAMETHAZINE)
Common 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
SULFAMETHAZINE [ORANGE BOOK]
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
TRISULFAPYRIMIDINES (SULFAMETHAZINE) [ORANGE BOOK]
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
SULFALOID COMPONENT SULFAMETHAZINE
Common Name English
SULFAMETHAZINE COMPONENT OF SULFOSE
Common Name English
SULFAMETHAZINE [USP MONOGRAPH]
Common Name English
SULFAMIDINE
Common Name English
SULFADIMIDINE [WHO-DD]
Common Name English
TERFONYL COMPONENT SULFAMETHAZINE
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 Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
CFR 21 CFR 520.445
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
WHO-VATC QJ01EW03
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
CFR 21 CFR 520.2218
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
CFR 21 CFR 520.2261A
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
WHO-VATC QP51AG01
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
NCI_THESAURUS C29739
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
CFR 21 CFR 558.630
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
WHO-VATC QG51AG02
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
CFR 21 CFR 520.2260A
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
WHO-VATC QJ01EQ03
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
CFR 21 CFR 520.2261B
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
CFR 21 CFR 558.145
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
WHO-ATC J01EE05
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
CFR 21 CFR 558.140
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
IARC Sulfamethazine
WHO-VATC QG51AG01
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
WHO-VATC QG51AG03
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
LIVERTOX 909
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
CFR 21 CFR 556.670
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
CFR 21 CFR 522.2260
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
CFR 21 CFR 558.145
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
WHO-VATC QJ51RC04
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
CFR 21 CFR 520.2260B
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
WHO-ATC J01EB03
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
CFR 21 CFR 558.140
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
CFR 21 CFR 520.2260
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
CFR 21 CFR 520.2260C
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
Code System Code Type Description
CAS
57-68-1
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
PRIMARY
INN
1068
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
PRIMARY
MERCK INDEX
M10317
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
PRIMARY Merck Index
EVMPD
SUB10699MIG
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
PRIMARY
MESH
C043086
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
SULFAMETHAZINE
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
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.
FDA UNII
48U51W007F
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
PRIMARY
MESH
D013418
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
PRIMARY
USP_CATALOG
1629000
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
PRIMARY USP-RS
HSDB
4157
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
PRIMARY
NCI_THESAURUS
C61960
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
PRIMARY
WIKIPEDIA
SULFADIMIDINE
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
PRIMARY
ChEMBL
CHEMBL446
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
PRIMARY
DRUG BANK
DB01582
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-346-4
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
PRIMARY
DRUG CENTRAL
2502
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
PRIMARY
RXCUI
10178
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
PRIMARY RxNorm
EPA CompTox
57-68-1
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
PRIMARY
PUBCHEM
5327
Created by admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
PRIMARY