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 NONE
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 No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Hydrogen bonding in sulfonamides.
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
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
Evaluation of conjugated linoleic acid and dietary antibiotics as growth promotants in weanling pigs.
2001 Oct
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
Development and implementation of the IPCS conceptual framework for evaluating mode of action of chemical carcinogens.
2002 Dec 27
Iminodibenzyl as a novel coupling agent for the spectrophotometric determination of sulfonamide derivatives.
2002 Mar
Stability of sulfonamides, nitrofurans, and chloramphenicol residues in preserved raw milk samples measured by liquid chromatography.
2002 Nov-Dec
[Rheological and biopharmaceutical investigation of polymer drug delivery systems].
2003
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
Interaction of ibuprofen and probenecid with drug metabolizing enzyme phenotyping procedures using caffeine as the probe drug.
2003 Feb
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
Antibiotics in dust originating from a pig-fattening farm: a new source of health hazard for farmers?
2003 Oct
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
Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers.
2004 Mar
Quantitative assessment of the reliability of identification by high-performance liquid chromatography-mass spectrometry.
2004 Mar 26
Effect of agricultural antibiotics on the persistence and transformation of 17beta-estradiol in a Sequatchie loam.
2005
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
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
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
by admin
on Thu Jul 06 23:07:00 UTC 2023
Edited
by admin
on Thu Jul 06 23:07:00 UTC 2023
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
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
Sulfadimidine [WHO-DD]
Common Name English
SULFAMETHAZINE [IARC]
Common Name English
SULFADIMIDINE [EP IMPURITY]
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
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
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 Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
CFR 21 CFR 520.445
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
WHO-VATC QJ01EW03
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
CFR 21 CFR 520.2218
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
CFR 21 CFR 520.2261A
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
WHO-VATC QP51AG01
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
NCI_THESAURUS C29739
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
CFR 21 CFR 558.630
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
WHO-VATC QG51AG02
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
CFR 21 CFR 520.2260A
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
WHO-VATC QJ01EQ03
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
CFR 21 CFR 520.2261B
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
CFR 21 CFR 558.145
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
WHO-ATC J01EE05
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
CFR 21 CFR 558.140
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
IARC Sulfamethazine
WHO-VATC QG51AG01
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
WHO-VATC QG51AG03
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
LIVERTOX 909
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
CFR 21 CFR 556.670
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
CFR 21 CFR 522.2260
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
CFR 21 CFR 558.145
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
WHO-VATC QJ51RC04
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
CFR 21 CFR 520.2260B
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
WHO-ATC J01EB03
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
CFR 21 CFR 558.140
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
CFR 21 CFR 520.2260
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
CFR 21 CFR 520.2260C
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
Code System Code Type Description
CAS
57-68-1
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
NSC
683529
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
INN
1068
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
MERCK INDEX
M10317
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY Merck Index
EVMPD
SUB10699MIG
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
MESH
C043086
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
SULFAMETHAZINE
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
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.
SMS_ID
100000089790
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
FDA UNII
48U51W007F
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
MESH
D013418
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
HSDB
4157
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
NCI_THESAURUS
C61960
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
WIKIPEDIA
SULFADIMIDINE
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
ChEMBL
CHEMBL446
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
NSC
67457
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
DRUG BANK
DB01582
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
CHEBI
102265
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-346-4
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
DRUG CENTRAL
2502
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
RXCUI
10178
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID6021290
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
DAILYMED
48U51W007F
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
RS_ITEM_NUM
1629000
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
PUBCHEM
5327
Created by admin on Thu Jul 06 23:07:01 UTC 2023 , Edited by admin on Thu Jul 06 23:07:01 UTC 2023
PRIMARY
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ACTIVE MOIETY