SULFAMETHAZINE

US Previously Marketed

First approved in 1947

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 Search

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
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).

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Bacterial dihydropteroate synthase 42 Target ID: CHEMBL2364668 Sources: https://www.genome.jp/dbget-bin/www_bget?dr:D02436\|https://www.ncbi.nlm.nih.gov/pubmed/21084778\|https://www.drugbank.ca/drugs/DB01582\|https://www.ncbi.nlm.nih.gov/pubmed/4577373	Inhibitor 7728
Target ID: UniProt: B6KBG5 (Dihydropteroate synthase) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2298911	Inhibitor 7728	5.7 µM [IC50]
Target ID: UniProt: B6KBG5 (Dihydropteroate synthase) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2298911	Inhibitor 7728	5.7 µM [IC50]
Bacterial dihydropteroate synthase 42 Target ID: CHEMBL2364668 Sources: https://www.genome.jp/dbget-bin/www_bget?dr:D02436 \| https://www.ncbi.nlm.nih.gov/pubmed/21084778 \| https://www.drugbank.ca/drugs/DB01582 \| https://www.ncbi.nlm.nih.gov/pubmed/4577373	Inhibitor 7728

Conditions

Condition	Modality	Targets	Highest Phase	Product
Infectious diseases (veterinary) 4 Sources: http://www.inchem.org/documents/jecfa/jecmono/v25je06.htm	Curative		Approved 8043	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).
Infectious diseases (veterinary) 4 Sources: http://www.inchem.org/documents/jecfa/jecmono/v25je06.htm	Curative		Approved 8043	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

Dose	Population	Adverse events
40 mg/kg single, oral Highest studied dose Dose: 40 mg/kg Route: oral Route: single Dose: 40 mg/kg Sources: https://www.ncbi.nlm.nih.gov/books/NBK396259/ https://pubmed.ncbi.nlm.nih.gov/759070	healthy n = 5 Health Status: healthy Sex: M Population Size: 5 Sources: https://www.ncbi.nlm.nih.gov/books/NBK396259/ https://pubmed.ncbi.nlm.nih.gov/759070	Sources: https://www.ncbi.nlm.nih.gov/books/NBK396259/ https://pubmed.ncbi.nlm.nih.gov/759070

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 707

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2C 10

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1772	inducer 1440 Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C 10	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/9293615/	yes [Ki 476 uM]

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:102265	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:102265
ChemicalBook	CB8116727	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8116727
MolPort	MolPort-000-887-465	https://www.molport.com/shop/molecule-link/MolPort-000-887-465
Selleck Chemicals	sulfamethazine	http://www.selleckchem.com/products/sulfamethazine.html
ZINC	ZINC000000057494	http://zinc15.docking.org/substances/ZINC000000057494
eMolecules	474320	https://www.emolecules.com/cgi-bin/more?vid=474320

PubMed

Title	Date	PubMed
Arylamine N-acetyltransferase activities in human breast cancer tissues.	2001	11478689
Molecular characterisation of aureocin A70, a multi-peptide bacteriocin isolated from Staphylococcus aureus.	2001 Aug 31	11531330
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	11453744
Determining the procedure for routine residue monitoring of sulfamethazine in edible animal tissues.	2001 Jun	11438963
Determination of selected sulfonamide antibiotics and trimethoprim in manure by electrospray and atmospheric pressure chemical ionization tandem mass spectrometry.	2002	11921244
Sulphonamide residues in eggs following drug administration via the drinking water.	2002 Apr	11962695
Quantification of veterinary antibiotics (sulfonamides and trimethoprim) in animal manure by liquid chromatography-mass spectrometry.	2002 Apr 5	12064522
Sex-dependent pharmacokinetics of S(-)-hydroxyhexamide, a pharmacologically active metabolite of acetohexamide, in rats.	2002 Dec	12458186
Use of optical biosensor technology to study immunological cross-reactivity between different sulfonamide drugs.	2002 Jan 15	11779109
[Rheological and biopharmaceutical investigation of polymer drug delivery systems].	2003	15112436
Determination of acidic pharmaceuticals, antibiotics and ivermectin in river sediment using liquid chromatography-tandem mass spectrometry.	2003 Dec 22	14735982
Preliminary evaluation of a lateral flow immunoassay device for screening urine samples for the presence of sulphamethazine.	2003 Jul	12957401
Separation and determination of the antitumor drug piritrexim by molecularly imprinted microspheres in high-performance liquid chromatography.	2003 Sep	12845402
Generation of group-specific antibodies against sulfonamides.	2003 Sep 24	13129281
[Determination of the hereditary and constitutive predisposition to peritoneal commissures].	2004	15462319
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	15317045
Validation of a confirmatory method for the determination of sulphonamides in muscle according to the European Union regulation 2002/657/EC.	2004 Apr 2	15065772
Antibiotic residues in edible tissues and antibiotic resistance of faecal Escherichia coli in pigs from Portugal.	2004 Aug	15370824
Sulfamethazine advances puberty in male chicks by effecting a rapid increase in gonadotropins.	2004 Feb	15123207
[Effect of starvation and acetone on the enzyme systems of biotransformation and toxicity of xenobiotics--CYP2E1 substrates in rats].	2004 Jan-Feb	15909426
Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers.	2004 Mar	14977870
Eukaryotic arylamine N-acetyltransferase. Investigation of substrate specificity by high-throughput screening.	2005 Jan 15	15627487
Surface runoff and transport of sulfonamide antibiotics and tracers on manured grassland.	2005 Jul-Aug	15998859
Cross-coupling of sulfonamide antimicrobial agents with model humic constituents.	2005 Jun 15	16047782
European Proficiency testing of national reference laboratories for the confirmation of sulfonamide residues in muscle and milk.	2005 Mar	16021791
Triplet-sensitized photodegradation of sulfa drugs containing six-membered heterocyclic groups: identification of an SO2 extrusion photoproduct.	2005 May 15	15952367
Confirmation of sulfamethazine, sulfathiazole, and sulfadimethoxine residues in condensed milk and soft-cheese products by liquid chromatography/tandem mass spectrometry.	2005 May-Jun	16001847
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	16273898
Occurrence of antibiotics in wastewater treatment facilities in Wisconsin, USA.	2006 May 15	16091289

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

In Vitro Use Guide

Unknown

Name

Type

Language

SULFAMETHAZINE

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

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