SULFAMETHIZOLE

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H10N4O2S2
Molecular Weight	270.331
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)S1

InChI

InChIKey=VACCAVUAMIDAGB-UHFFFAOYSA-N

InChI=1S/C9H10N4O2S2/c1-6-11-12-9(16-6)13-17(14,15)8-4-2-7(10)3-5-8/h2-5H,10H2,1H3,(H,12,13)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13202246 | https://www.ncbi.nlm.nih.gov/pubmed/2298911

Sulfamethizole is an oral antiobiotic, which was used against urinary tract infections under the name Thiosulfil. Sulfamethizole blocks bacterial growth by inhibiting folic acid synthesis via enzyme called dihydropteroate synthase. The drug is no longer marketed in the USA.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial dihydropteroate synthase 44 Target ID: CHEMBL2364668 Sources: http://new.dhh.louisiana.gov/assets/oph/Center-PHCH/Center-CH/infectious-epi/VetInfo/VetAntibioResSen/LADDL/AntimicrobialClasses/sulfonamides/Sulfonamides.pdf	Inhibitor 8504		7.9 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 207 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13202246	Curative		Approved 8583	THIOSULFIL Approved Use For urinary tract infections. Launch Date 1953

C_max

Value	Dose	Co-administered	Analyte	Population
62.88 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/702289/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		SULFAMETHIZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
144 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/702289/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		SULFAMETHIZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/702289/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		SULFAMETHIZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 2438

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10725317/	yes		yes (co-administration study) Comment: can't access journal; 1.6-fold increase in tolbutamide AUC was predicted, which agreed well with reported increases in humans Sources: https://pubmed.ncbi.nlm.nih.gov/10725317/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9331	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9331
ChemicalBook	CB4266501	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4266501
ChemicalBook	CB72646481	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB72646481
eMolecules	511883	https://www.emolecules.com/cgi-bin/more?vid=511883
MolPort	MolPort-000-876-475	https://www.molport.com/shop/molecule-link/MolPort-000-876-475
Selleck Chemicals	Sulfamethizole(Proklar)	http://www.selleckchem.com/products/Sulfamethizole(Proklar).html
ZINC	ZINC000000057493	http://zinc15.docking.org/substances/ZINC000000057493

PubMed

Title	Date	PubMed
Aqueous photocatalytic oxidation of sulfamethizole.	2010-12-14	21275251
Prevalence of G6PD deficiency in a large cohort of HIV-infected patients.	2010-11	20732351
(14)N NQR, (1)H NMR and DFT/QTAIM study of hydrogen bonding and polymorphism in selected solid 1,3,4-thiadiazole derivatives.	2010-10-28	20820552
Putative-farnesoic acid O-methyltransferase (FAMeT) in medfly reproduction.	2010-10	20824822
Marine polysaccharides in pharmaceutical applications: an overview.	2010-09-02	20948899
Trimethoprim-sulfamethoxazole-induced hyperkalemia in patients receiving inhibitors of the renin-angiotensin system: a population-based study.	2010-06-28	20585070
Antibiotic immunosensing: determination of sulfathiazole in water and honey.	2010-06-15	20441943
Effects of short-term oral administration of trimethoprim-sulfamethoxazole on Schirmer II tear test results in clinically normal rabbits.	2010-05-15	20472874
Removal of sulfadiazine, sulfamethizole, sulfamethoxazole, and sulfathiazole from aqueous solution by ozonation.	2010-05	20303138
Biodegradation of pharmaceuticals by Rhodococcus rhodochrous and Aspergillus niger by co-metabolism.	2010-03-01	20089297
Evolution and functional divergence of enzymes involved in sesquiterpenoid hormone biosynthesis in crustaceans and insects.	2010-03	19836428
The putative-farnesoic acid O-methyl transferase (FAMeT) gene of Ceratitis capitata: characterization and pre-imaginal life expression.	2010-02	20077571
Cloning and characterization of a putative farnesoic acid O-methyltransferase gene from the brown planthopper, Nilaparvata lugens.	2010	20874390
A confirmatory method for the simultaneous extraction, separation, identification and quantification of Tetracycline, Sulphonamide, Trimethoprim and Dapsone residues in muscle by ultra-high-performance liquid chromatography-tandem mass spectrometry according to Commission Decision 2002/657/EC.	2009-11-13	19586630
Analysis of antimicrobial resistance and plasmid profiles in Salmonella serovars associated with tropical seafood of India.	2009-06	19422307
Purification of nine sulfonamides from chicken tissues by immunoaffinity chromatography using two monoclonal antibodies.	2009-02-11	19202813
Pivmecillinam versus sulfamethizole for short-term treatment of uncomplicated acute cystitis in general practice: a randomized controlled trial.	2009	18991182
Differential expression profiling of components associated with exoskeletal hardening in crustaceans.	2008-12-01	19040762
[What are we learning about Staphylococcus saprophyticus?].	2008-10	19094862
Multiresidue determination of sulfonamides in chicken meat by polymer monolith microextraction and capillary zone electrophoresis with field-amplified sample stacking.	2008-09-26	18723177
Simultaneous determination of sulfonamides, tetracyclines and tiamulin in swine wastewater by solid-phase extraction and liquid chromatography-mass spectrometry.	2008-08-22	18649883
Gastric emptying for liquids and solids after distal gastrectomy with Billroth-I reconstruction.	2008-08-19	18705346
Toxicology profile of N-methyl-D-aspartate antagonists delivered by intrathecal infusion in the canine model.	2008-05	18431131
Risk of miscarriage for pregnant users of pivmecillinam: a population-based case-control study.	2008-04	18397462
Predictors of antimicrobial-resistant Escherichia coli in the feces of vegetarians and newly hospitalized adults in Minnesota and Wisconsin.	2008-02-01	18184093
A putative farnesoic acid O-methyltransferase (FAMeT) orthologue in Drosophila melanogaster (CG10527): relationship to juvenile hormone biosynthesis?	2008-02	18242777
Farnesoic acid O-methyl transferase (FAMeT) isoforms: conserved traits and gene expression patterns related to caste differentiation in the stingless bee, Melipona scutellaris.	2008-02	18076110
[A case of Salmonella paratyphi A infection in Poland].	2008	18663912
Optimizing therapy for Stenotrophomonas maltophilia.	2007-12	18095231
Analytical methods for multiresidue determination of sulfonamides and trimethoprim in meat and ground water samples by CE-MS and CE-MS/MS.	2007-11	17960854
Gene expression profiling of cuticular proteins across the moult cycle of the crab Portunus pelagicus.	2007-10-10	17925039
Free-radical-induced oxidative and reductive degradation of sulfa drugs in water: absolute kinetics and efficiencies of hydroxyl radical and hydrated electron reactions.	2007-09-20	17715905
Clinical studies with oral lipid based formulations of poorly soluble compounds.	2007-08	18472981
Determination of sulfonamides in milk after precolumn derivatisation by micellar liquid chromatography.	2007-06-19	17543601
Comparison of Salmonella enterica serovar Heidelberg susceptibility testing results.	2007-06	17607044
Determination of 10 sulfonamide residues in meat samples by liquid chromatography with ultraviolet detection.	2007-05-04	17474530
Simultaneous determination of 17 sulfonamides and the potentiators ormetoprim and trimethoprim in salmon muscle by liquid chromatography with tandem mass spectrometry detection.	2007-03-22	17373466
Development of an enzyme-linked immunosorbent assay for seven sulfonamide residues and investigation of matrix effects from different food samples.	2007-03-21	17300200
Development of a group-specific immunoassay for sulfonamides. Application to bee honey analysis.	2007-02-15	19071396
Cholestatic hepatitis with severe systemic reactions induced by trimethoprim-sulfamethoxazole.	2007-02-14	17297432
Electrocardiographic changes after shoulder arthroplasty.	2007-01-08	18790340
In-vitro antifungal activities of sulfa drugs against clinical isolates of Aspergillus and Cryptococcus species.	2007	17287722
Oxidation of sulfonamide antimicrobials by ferrate(VI) [Fe(VI)O4(2-)].	2006-12-01	17180970
Multiresidue determination of sulfonamides in a variety of biological matrices by supported liquid membrane with high pressure liquid chromatography-electrospray mass spectrometry detection.	2004-09-08	18969572
Interaction of Pneumocystis carinii dihydropteroate synthase with sulfonamides and diaminodiphenyl sulfone (dapsone).	1994-02	8106784
[Effects of drugs on the liver. A review illustrated with 3 clinical cases].	1994-01-10	7669097
Inhibition of bioluminescence in Photobacterium phosphoreum by sulfamethizole and its stimulation by thymine.	1990-06-26	2372557
Interaction of sulfonamide and sulfone compounds with Toxoplasma gondii dihydropteroate synthase.	1990-02	2298911
Drugs as allergens: detection and combining site specificities of IgE antibodies to sulfamethoxazole.	1988-12	3237218
Studies of human IgE to a sulfonamide determinant.	1987-03	2434548

Patents

Sample Use Guides

In Vivo Use Guide

Sulfamethizole is given orally at a dose of 1 gram twice daily for three days.

Route of Administration: Oral

In Vitro Use Guide

MIC values for Sulfamethizole were: 64 ug/ml (KMA-4845 and KMA-21476 E.coli strains), 128 ug/ml (KMA-26883 strain), 512 ug/ml (21804403-132 and UVI-203 strains), 1024 ug/ml (UVI-202 and 21398355-97 strains).

Name

Type

Language

THIOSULFIL

Preferred Name

English

SULFAMETHIZOLE

Official Name

English

NSC-757327

Code

English

SULFAMETHIZOLE [ORANGE BOOK]

Common Name

English

SULPHAMETHIZOLE

Common Name

English

SULFAMETHIZOLE [EP IMPURITY]

Common Name

English

N (SUP 1)-(5-METHYL-1,3,4-THIADIAZOL-2-YL)SULFANILAMIDE

Systematic Name

English

sulfamethizole [INN]

Common Name

English

SULFAMETHIZOLE [MART.]

Common Name

English

SULFAMETHIZOLE [VANDF]

Common Name

English

BENZENESULFONAMIDE, 4-AMINO-N-(5-METHYL-1,3,4-THIADIAZOL-2-YL)-

Systematic Name

English

SULFAMETHIZOLE [MI]

Common Name

English

SULFAMETHIZOLE [EP MONOGRAPH]

Common Name

English

SULFAMETHIZOLE [HSDB]

Common Name

English

SULFAMETHIZOLE [JAN]

Common Name

English

SULFAMETHIZOLE [USP MONOGRAPH]

Common Name

English

Sulfamethizole [WHO-DD]

Common Name

English

SULFAMETHIZOLE [USP-RS]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 520.2280