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 8297		7.9 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13202246	Curative		Approved 8429	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 1767

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C9 1819	inhibitor 3277 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
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
eMolecules	511883	https://www.emolecules.com/cgi-bin/more?vid=511883

PubMed

Title	Date	PubMed
Studies of human IgE to a sulfonamide determinant.	1987 Mar	2434548
Drugs as allergens: detection and combining site specificities of IgE antibodies to sulfamethoxazole.	1988 Dec	3237218
Interaction of sulfonamide and sulfone compounds with Toxoplasma gondii dihydropteroate synthase.	1990 Feb	2298911
Inhibition of bioluminescence in Photobacterium phosphoreum by sulfamethizole and its stimulation by thymine.	1990 Jun 26	2372557
Interaction of Pneumocystis carinii dihydropteroate synthase with sulfonamides and diaminodiphenyl sulfone (dapsone).	1994 Feb	8106784
[Effects of drugs on the liver. A review illustrated with 3 clinical cases].	1994 Jan 10	7669097
Multiresidue determination of sulfonamides in a variety of biological matrices by supported liquid membrane with high pressure liquid chromatography-electrospray mass spectrometry detection.	2004 Sep 8	18969572
Exacerbation of Whipple's disease associated with infliximab treatment.	2005 Mar-Apr	16095013
[Determination of residual sulfonamides in meat by high performance liquid chromatography with solid-phase extraction].	2005 Nov	16498995
Antifungal and antibacterial resistance profiles between Cambodia and Kenyan children with human immunodeficiency virus infections receiving trimethoprim-sulfamethoxazole prophylaxis.	2005 Nov	16282953
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.	2005 Sep-Oct	16385979
Prevalence of multidrug-resistant Salmonella on ready-to-eat betel leaves (Paan) and in water used for soaking betel leaves in North Indian cities.	2006 Feb	16496567
Application of capillary zone electrophoresis with large-volume sample stacking to the sensitive determination of sulfonamides in meat and ground water.	2006 Oct	16991204
Determination of antimicrobials in sludge from infiltration basins at two artificial recharge plants by pressurized liquid extraction-liquid chromatography-tandem mass spectrometry.	2006 Oct 13	16822516
Intracranial Nocardia recurrence during fluorinated quinolones therapy.	2006 Sep	16913975
Clinical studies with oral lipid based formulations of poorly soluble compounds.	2007 Aug	18472981
Optimizing therapy for Stenotrophomonas maltophilia.	2007 Dec	18095231
Development of a group-specific immunoassay for sulfonamides. Application to bee honey analysis.	2007 Feb 15	19071396
Simultaneous determination of 17 sulfonamides and the potentiators ormetoprim and trimethoprim in salmon muscle by liquid chromatography with tandem mass spectrometry detection.	2007 Jan-Feb	17373466
Comparison of Salmonella enterica serovar Heidelberg susceptibility testing results.	2007 Jun	17607044
Determination of 10 sulfonamide residues in meat samples by liquid chromatography with ultraviolet detection.	2007 Mar-Apr	17474530
Analytical methods for multiresidue determination of sulfonamides and trimethoprim in meat and ground water samples by CE-MS and CE-MS/MS.	2007 Nov	17960854
Gene expression profiling of cuticular proteins across the moult cycle of the crab Portunus pelagicus.	2007 Oct 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 Sep 20	17715905
[A case of Salmonella paratyphi A infection in Poland].	2008	18663912
Risk of miscarriage for pregnant users of pivmecillinam: a population-based case-control study.	2008 Apr	18397462
Simultaneous determination of sulfonamides, tetracyclines and tiamulin in swine wastewater by solid-phase extraction and liquid chromatography-mass spectrometry.	2008 Aug 22	18649883
Differential expression profiling of components associated with exoskeletal hardening in crustaceans.	2008 Dec 1	19040762
A putative farnesoic acid O-methyltransferase (FAMeT) orthologue in Drosophila melanogaster (CG10527): relationship to juvenile hormone biosynthesis?	2008 Feb	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 Feb	18076110
Predictors of antimicrobial-resistant Escherichia coli in the feces of vegetarians and newly hospitalized adults in Minnesota and Wisconsin.	2008 Feb 1	18184093
Toxicology profile of N-methyl-D-aspartate antagonists delivered by intrathecal infusion in the canine model.	2008 May	18431131
Gastric emptying for liquids and solids after distal gastrectomy with Billroth-I reconstruction.	2008 May-Jun	18705346
Purification of nine sulfonamides from chicken tissues by immunoaffinity chromatography using two monoclonal antibodies.	2008 Nov-Dec	19202813
[What are we learning about Staphylococcus saprophyticus?].	2008 Oct	19094862
Multiresidue determination of sulfonamides in chicken meat by polymer monolith microextraction and capillary zone electrophoresis with field-amplified sample stacking.	2008 Sep 26	18723177
Electrocardiographic changes after shoulder arthroplasty.	2008 Sep-Oct	18790340
Pivmecillinam versus sulfamethizole for short-term treatment of uncomplicated acute cystitis in general practice: a randomized controlled trial.	2009	18991182
Analysis of antimicrobial resistance and plasmid profiles in Salmonella serovars associated with tropical seafood of India.	2009 Jun	19422307
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 Nov 13	19586630
Cloning and characterization of a putative farnesoic acid O-methyltransferase gene from the brown planthopper, Nilaparvata lugens.	2010	20874390
Aqueous photocatalytic oxidation of sulfamethizole.	2010 Dec 14	21275251
The putative-farnesoic acid O-methyl transferase (FAMeT) gene of Ceratitis capitata: characterization and pre-imaginal life expression.	2010 Feb	20077571
Antibiotic immunosensing: determination of sulfathiazole in water and honey.	2010 Jun 15	20441943
Trimethoprim-sulfamethoxazole-induced hyperkalemia in patients receiving inhibitors of the renin-angiotensin system: a population-based study.	2010 Jun 28	20585070
Evolution and functional divergence of enzymes involved in sesquiterpenoid hormone biosynthesis in crustaceans and insects.	2010 Mar	19836428
Biodegradation of pharmaceuticals by Rhodococcus rhodochrous and Aspergillus niger by co-metabolism.	2010 Mar 1	20089297
Removal of sulfadiazine, sulfamethizole, sulfamethoxazole, and sulfathiazole from aqueous solution by ozonation.	2010 May	20303138
Effects of short-term oral administration of trimethoprim-sulfamethoxazole on Schirmer II tear test results in clinically normal rabbits.	2010 May 15	20472874
Marine polysaccharides in pharmaceutical applications: an overview.	2010 Sep 2	20948899

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

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

THIOSULFIL

Brand Name

English

Sulfamethizole [WHO-DD]

Common Name

English

SULFAMETHIZOLE [USP-RS]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 520.2280