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

Molecular Formula	C9H10N4O2S2
Molecular Weight	270.331
Charge	0
Count

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

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
Interaction of Pneumocystis carinii dihydropteroate synthase with sulfonamides and diaminodiphenyl sulfone (dapsone).	1994 Feb	8106784
Treatment failures after antibiotic therapy of uncomplicated urinary tract infections. A prescription database study.	2002 Jun	12184721
Class I integrons and SXT elements in El Tor strains isolated before and after 1992 Vibrio cholerae O139 outbreak, Calcutta, India.	2003 Apr	12702236
Clinical efficacy of trimethoprim/sulfadiazine and procaine penicillin G in a Streptococcus equi subsp. zooepidemicus infection model in ponies.	2003 Aug	12887605
Comparative immunohistochemistry and cellular distribution of farnesoic acid O-methyltransferase in the shrimp and the crayfish.	2003 Oct	14706538
[Prescriptions of a new antibiotic following treatment with sulfamethizole or pivmecillinam].	2003 Sep 22	14558387
Resistance of uropathogens in symptomatic urinary tract infections in León, Nicaragua.	2004 May	15120732
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
Antibiotic resistance and antibacterial activity in heterotrophic bacteria of mineral water origin.	2005 Jun 15	15993695
[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
Multiresidue determination of sulfonamides in edible catfish, shrimp and salmon tissues by high-performance liquid chromatography with postcolumn derivatization and fluorescence detection.	2006 Aug 18	16750659
Oxidation of sulfonamides, macrolides, and carbadox with free chlorine and monochloramine.	2006 Jul	16790259
Transfection of drug-specific T-cell receptors into hybridoma cells: tools to monitor drug interaction with T-cell receptors and evaluate cross-reactivity to related compounds.	2006 Jul	16617162
Absence of dihydropteroate synthase mutations in Pneumocystis jirovecii from Brazilian AIDS patients.	2006 Jul-Aug	16872298
Variability in antimicrobial resistance among Salmonella enterica strains from fattening pigs and sows.	2006 Spring	16584313
In-vitro antifungal activities of sulfa drugs against clinical isolates of Aspergillus and Cryptococcus species.	2007	17287722
Optimizing therapy for Stenotrophomonas maltophilia.	2007 Dec	18095231
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
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
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
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
[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
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
Antibiotic immunosensing: determination of sulfathiazole in water and honey.	2010 Jun 15	20441943
Effects of short-term oral administration of trimethoprim-sulfamethoxazole on Schirmer II tear test results in clinically normal rabbits.	2010 May 15	20472874
Prevalence of G6PD deficiency in a large cohort of HIV-infected patients.	2010 Nov	20732351
Putative-farnesoic acid O-methyltransferase (FAMeT) in medfly reproduction.	2010 Oct	20824822

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).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:01:54 GMT 2023` Edited by `admin` on `Fri Dec 15 15:01:54 GMT 2023`
Record UNII	25W8454H16
Record Status	`Validated (UNII)`
Record Version

Download

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