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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
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
The teratogenic risk of trimethoprim-sulfonamides: a population based case-control study.
2001 Nov-Dec
Sulphonamide residues in eggs following drug administration via the drinking water.
2002 Apr
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
Bioconcentration and elimination of sulfamethazine and its main metabolite in sturgeon (Acipenser schrenkii).
2003 Dec 17
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
Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions.
2004 Jul-Aug
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
[Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry].
2005 Jul
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
Triplet-sensitized photodegradation of sulfa drugs containing six-membered heterocyclic groups: identification of an SO2 extrusion photoproduct.
2005 May 15
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
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 Sun Dec 18 20:49:56 UTC 2022
Edited
by admin
on Sun Dec 18 20:49:56 UTC 2022
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 Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
CFR 21 CFR 520.445
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
WHO-VATC QJ01EW03
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
CFR 21 CFR 520.2218
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
CFR 21 CFR 520.2261A
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
WHO-VATC QP51AG01
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
NCI_THESAURUS C29739
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
CFR 21 CFR 558.630
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
WHO-VATC QG51AG02
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
CFR 21 CFR 520.2260A
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
WHO-VATC QJ01EQ03
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
CFR 21 CFR 520.2261B
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
CFR 21 CFR 558.145
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
WHO-ATC J01EE05
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
CFR 21 CFR 558.140
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
IARC Sulfamethazine
WHO-VATC QG51AG01
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
WHO-VATC QG51AG03
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
LIVERTOX 909
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
CFR 21 CFR 556.670
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
CFR 21 CFR 522.2260
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
CFR 21 CFR 558.145
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
WHO-VATC QJ51RC04
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
CFR 21 CFR 520.2260B
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
WHO-ATC J01EB03
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
CFR 21 CFR 558.140
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
CFR 21 CFR 520.2260
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
CFR 21 CFR 520.2260C
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
Code System Code Type Description
CAS
57-68-1
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
NSC
683529
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
INN
1068
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
MERCK INDEX
M10317
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY Merck Index
EVMPD
SUB10699MIG
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
MESH
C043086
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
SULFAMETHAZINE
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
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 Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
MESH
D013418
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
HSDB
4157
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
NCI_THESAURUS
C61960
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
WIKIPEDIA
SULFADIMIDINE
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
ChEMBL
CHEMBL446
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
NSC
67457
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
DRUG BANK
DB01582
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
CHEBI
102265
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
ECHA (EC/EINECS)
200-346-4
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
DRUG CENTRAL
2502
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
RXCUI
10178
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY RxNorm
EPA CompTox
DTXSID6021290
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
DAILYMED
48U51W007F
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
RS_ITEM_NUM
1629000
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
PUBCHEM
5327
Created by admin on Sun Dec 18 20:49:58 UTC 2022 , Edited by admin on Sun Dec 18 20:49:58 UTC 2022
PRIMARY
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