SULFAMETHAZINE BISULFATE

US Previously Marketed

First approved in 1947

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H14N4O2S.H2O4S
Molecular Weight	376.409
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(O)(=O)=O.CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=N1

InChI

InChIKey=SOHZBANIDAJXHD-UHFFFAOYSA-N

InChI=1S/C12H14N4O2S.H2O4S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11;1-5(2,3)4/h3-7H,13H2,1-2H3,(H,14,15,16);(H2,1,2,3,4)

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

Molecular Formula	H2O4S
Molecular Weight	98.078
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 44 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 8146
Target ID: UniProt: B6KBG5 (Dihydropteroate synthase) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2298911	Inhibitor 8146	5.7 µM [IC50]
Target ID: UniProt: B6KBG5 (Dihydropteroate synthase) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2298911	Inhibitor 8146	5.7 µM [IC50]
Bacterial dihydropteroate synthase 44 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 8146

Conditions

Condition	Modality	Targets	Highest Phase	Product
Infectious diseases (veterinary) 4 Sources: http://www.inchem.org/documents/jecfa/jecmono/v25je06.htm	Curative		Approved 8307	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 8307	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 753

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2C 11

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1857	inducer 1515 Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C 11	substrate 3264 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
Sulphonamide residues in eggs following drug administration via the drinking water.	2002 Apr	11962695
Sex-dependent pharmacokinetics of S(-)-hydroxyhexamide, a pharmacologically active metabolite of acetohexamide, in rats.	2002 Dec	12458186
A new, sensitive, and rapid spectrophotometric method for the determination of sulfa drugs.	2002 Jul-Aug	12180680
Determination of sulfonamide residues in eggs by liquid chromatography.	2002 Jul-Aug	12180677
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	12358081
Functional genomics of C190T single nucleotide polymorphism in human N-acetyltransferase 2.	2002 Jun	12222688
Rapid and sensitive screening of sulfamethazine in porcine urine with an enzyme-linked immunosorbent assay and a field-portable immunofiltration assay.	2002 May	12030294
[Rheological and biopharmaceutical investigation of polymer drug delivery systems].	2003	15112436
A clean and rapid liquid chromatographic technique for sulfamethazine monitoring in pork tissues without using organic solvents.	2003 Aug	12908955
A sensitive method for detection of sulfamethazine and N4-acetylsulfamethazine residues in environmental samples using solid phase immunoextraction coupled with MALDI-TOF MS.	2003 Aug 27	12926885
Bioconcentration and elimination of sulfamethazine and its main metabolite in sturgeon (Acipenser schrenkii).	2003 Dec 17	14664536
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	14503661
Generation and functional characterization of arylamine N-acetyltransferase Nat1/Nat2 double-knockout mice.	2003 Jul	12815173
[Determination of sulfamethazine and sulfamethoxazole in muscle of chicken by high performance liquid chromatography].	2003 Nov	14963923
[Determination of the hereditary and constitutive predisposition to peritoneal commissures].	2004	15462319
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
Chemometric and derivative methods as flexible spectrophotometric approaches for dissolution and assaying tests in multicomponent tablets.	2004 Aug	15262532
Quantitative analysis of twelve sulfonamides in honey after acidic hydrolysis by high-performance liquid chromatography with post-column derivatization and fluorescence detection.	2004 Aug 20	15481463
Routine monitoring of antibiotics in water and wastewater with a radioimmunoassay technique.	2004 Aug-Sep	15276731
Sulfamethazine advances puberty in male chicks by effecting a rapid increase in gonadotropins.	2004 Feb	15123207
Automated microarray system for the simultaneous detection of antibiotics in milk.	2004 Feb 1	14750859
[Effect of starvation and acetone on the enzyme systems of biotransformation and toxicity of xenobiotics--CYP2E1 substrates in rats].	2004 Jan-Feb	15909426
Antimicrobial use in the treatment of calf diarrhea.	2004 Jan-Feb	14765726
Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions.	2004 Jul-Aug	15254115
Possible association between different congenital abnormalities and use of different sulfonamides during pregnancy.	2004 Jun	15198720
Quantitative assessment of the reliability of identification by high-performance liquid chromatography-mass spectrometry.	2004 Mar 26	15058563
Administration of and withdrawal periods for sulphadimidine solution.	2004 Sep 18	15493612
Determination of sulfonamide residues in the tissues of food animals using automated precolumn derivatization and liquid chromatography with fluorescence detection.	2004 Sep-Oct	15493686
Effect of agricultural antibiotics on the persistence and transformation of 17beta-estradiol in a Sequatchie loam.	2005	16190018
Microbial inhibition by pharmaceutical antibiotics in different soils--dose-response relations determined with the iron(III) reduction test.	2005 Apr	15839561
Different behavior of tetracyclines and sulfonamides in sandy soils after repeated fertilization with liquid manure.	2005 Apr	15839560
Test-plot studies on runoff of sulfonamides from manured soils after sprinkler irrigation.	2005 Apr	15839549
Proteomic analysis using an unfinished bacterial genome: the effects of subminimum inhibitory concentrations of antibiotics on Mannheimia haemolytica virulence factor expression.	2005 Dec	16247735
[Effect of sulphamethazine on the gene expression of FRTL-5 cells].	2005 Jan	15862012
Eukaryotic arylamine N-acetyltransferase. Investigation of substrate specificity by high-throughput screening.	2005 Jan 15	15627487
[Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry].	2005 Jul	16250451
Photocatalytic oxidation of sulfamethazine.	2005 Jul	15924956
Surface runoff and transport of sulfonamide antibiotics and tracers on manured grassland.	2005 Jul-Aug	15998859
Evaluating the biodegradability of sulfamethazine, sulfamethoxazole, sulfathiazole, and trimethoprim at different stages of sewage treatment.	2005 Jun	16117111
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
Effects of mannan oligosaccharide and an antimicrobial product in nursery diets on performance of pigs reared on three different farms.	2005 Nov	16230663
Monitoring of five sulfonamide antibacterial residues in milk by in-tube solid-phase microextraction coupled to high-performance liquid chromatography.	2005 Nov 2	16248539
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
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	15880531
Dispersive solid-phase extraction for the determination of sulfonamides in chicken muscle by liquid chromatography.	2005 Sep 16	16130722
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	16239091
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

Substance Class	Chemical Created by `admin` on `Fri Dec 16 20:25:22 UTC 2022` Edited by `admin` on `Fri Dec 16 20:25:22 UTC 2022`
Record UNII	5J847L84W0
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

SULFAMETHAZINE BISULFATE

Common Name

English

SULPHAMETHAZINE BISULPHATE

Common Name

English

SULFAMETHAZINE BISULFATE [GREEN BOOK]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29739