SULFAMETHAZINE

US Previously Marketed

First approved in 1947

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 Search

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
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
Hydrogen bonding in sulfonamides.	2001 Dec	11745765
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
The teratogenic risk of trimethoprim-sulfonamides: a population based case-control study.	2001 Nov-Dec	11738517
Sulphonamide residues in eggs following drug administration via the drinking water.	2002 Apr	11962695
A new, sensitive, and rapid spectrophotometric method for the determination of sulfa drugs.	2002 Jul-Aug	12180680
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
Bioconcentration and elimination of sulfamethazine and its main metabolite in sturgeon (Acipenser schrenkii).	2003 Dec 17	14664536
Chemometric and derivative methods as flexible spectrophotometric approaches for dissolution and assaying tests in multicomponent tablets.	2004 Aug	15262532
Routine monitoring of antibiotics in water and wastewater with a radioimmunoassay technique.	2004 Aug-Sep	15276731
Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions.	2004 Jul-Aug	15254115
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
[Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry].	2005 Jul	16250451
Surface runoff and transport of sulfonamide antibiotics and tracers on manured grassland.	2005 Jul-Aug	15998859
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
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

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 `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

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

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