SULFATHIAZOLE

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H9N3O2S2
Molecular Weight	255.317
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=CC=C(C=C1)S(=O)(=O)NC2=NC=CS2

InChI

InChIKey=JNMRHUJNCSQMMB-UHFFFAOYSA-N

InChI=1S/C9H9N3O2S2/c10-7-1-3-8(4-2-7)16(13,14)12-9-11-5-6-15-9/h1-6H,10H2,(H,11,12)

HIDE SMILES / InChI

Description
Sources: http://www.sciencedirect.com/science/article/pii/B9780080552323633343 | http://www.rxlist.com/sultrin-drug.htm
Curator's Comment: Description was created based on several sources, including http://www.mims.com/india/drug/info/sulfathiazole?type=full&mtype=generic#Indications

Sulfathiazole is a short-acting sulfonamide with properties similar to those of sulfamethoxazole. It is now rarely used systemically due to its toxicity. Sulfathiazole is used with other sulfonamides, usually sulfabenzamide and sulfacetamide, in preparations for the topical treatment of vaginal infections and is also used with other drugs in the treatment of skin infections. Sulfathiazole sodium has been applied topically with other drugs in the treatment of eye infections. Sulfathiazole interferes with nucleic acid synthesis in microorganisms by blocking the conversion of p-aminobenzoic acid to the coenzyme dihydrofolic acid.It has properties similar to sulfamethoxazole.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Escherichia coli 82 Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16561456	Inhibitor 8297
folic acid biosynthetic process 9 Target ID: GO:0046656 Sources: https://www.genome.jp/dbget-bin/www_bget?D07060+D02447	Inhibitor 8297
Bacterial dihydropteroate synthase 44 Target ID: CHEMBL2364668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14700578 \| https://www.drugbank.ca/drugs/DB06147 \| https://www.ncbi.nlm.nih.gov/pubmed/2694948	Inhibitor 8297
Escherichia coli 82 Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26428163	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vaginal infections 8 Sources: http://www.mims.com/india/drug/info/sulfathiazole?mtype=generic http://www.rxlist.com/sultrin-drug.htm	Curative		Approved 8429	Sulfathiazole Approved Use Vaginal infections

Doses

Dose	Population	Adverse events
1 g 6 times / day multiple, oral Recommended Dose: 1 g, 6 times / day Route: oral Route: multiple Dose: 1 g, 6 times / day Sources: https://jamanetwork.com/journals/jama/article-abstract/307661	unhealthy n = 100 Health Status: unhealthy Condition: infection Population Size: 100 Sources: https://jamanetwork.com/journals/jama/article-abstract/307661	Disc. AE: Dermatitis, Nausea and vomiting... Other AEs: Nitrogen retention, Hematuria... AEs leading to discontinuation/dose reduction: Dermatitis (9%) Nausea and vomiting (6%) Other AEs: Nitrogen retention (1%) Hematuria (1%) Drug fever (2%) Burning eyes (2%) Conjunctival injection (1%) Anemia (1%) Sources: https://jamanetwork.com/journals/jama/article-abstract/307661

AEs

AE	Significance	Dose	Population
Anemia	1%	1 g 6 times / day multiple, oral Recommended Dose: 1 g, 6 times / day Route: oral Route: multiple Dose: 1 g, 6 times / day Sources: https://jamanetwork.com/journals/jama/article-abstract/307661	unhealthy n = 100 Health Status: unhealthy Condition: infection Population Size: 100 Sources: https://jamanetwork.com/journals/jama/article-abstract/307661
Conjunctival injection	1%	1 g 6 times / day multiple, oral Recommended Dose: 1 g, 6 times / day Route: oral Route: multiple Dose: 1 g, 6 times / day Sources: https://jamanetwork.com/journals/jama/article-abstract/307661	unhealthy n = 100 Health Status: unhealthy Condition: infection Population Size: 100 Sources: https://jamanetwork.com/journals/jama/article-abstract/307661
Hematuria	1%	1 g 6 times / day multiple, oral Recommended Dose: 1 g, 6 times / day Route: oral Route: multiple Dose: 1 g, 6 times / day Sources: https://jamanetwork.com/journals/jama/article-abstract/307661	unhealthy n = 100 Health Status: unhealthy Condition: infection Population Size: 100 Sources: https://jamanetwork.com/journals/jama/article-abstract/307661
Nitrogen retention	1%	1 g 6 times / day multiple, oral Recommended Dose: 1 g, 6 times / day Route: oral Route: multiple Dose: 1 g, 6 times / day Sources: https://jamanetwork.com/journals/jama/article-abstract/307661	unhealthy n = 100 Health Status: unhealthy Condition: infection Population Size: 100 Sources: https://jamanetwork.com/journals/jama/article-abstract/307661
Burning eyes	2%	1 g 6 times / day multiple, oral Recommended Dose: 1 g, 6 times / day Route: oral Route: multiple Dose: 1 g, 6 times / day Sources: https://jamanetwork.com/journals/jama/article-abstract/307661	unhealthy n = 100 Health Status: unhealthy Condition: infection Population Size: 100 Sources: https://jamanetwork.com/journals/jama/article-abstract/307661
Drug fever	2%	1 g 6 times / day multiple, oral Recommended Dose: 1 g, 6 times / day Route: oral Route: multiple Dose: 1 g, 6 times / day Sources: https://jamanetwork.com/journals/jama/article-abstract/307661	unhealthy n = 100 Health Status: unhealthy Condition: infection Population Size: 100 Sources: https://jamanetwork.com/journals/jama/article-abstract/307661
Nausea and vomiting	6% Disc. AE	1 g 6 times / day multiple, oral Recommended Dose: 1 g, 6 times / day Route: oral Route: multiple Dose: 1 g, 6 times / day Sources: https://jamanetwork.com/journals/jama/article-abstract/307661	unhealthy n = 100 Health Status: unhealthy Condition: infection Population Size: 100 Sources: https://jamanetwork.com/journals/jama/article-abstract/307661
Dermatitis	9% Disc. AE	1 g 6 times / day multiple, oral Recommended Dose: 1 g, 6 times / day Route: oral Route: multiple Dose: 1 g, 6 times / day Sources: https://jamanetwork.com/journals/jama/article-abstract/307661	unhealthy n = 100 Health Status: unhealthy Condition: infection Population Size: 100 Sources: https://jamanetwork.com/journals/jama/article-abstract/307661

Sourcing

Vendor/Aggregator	ID	URL
ChemIDplus	10135894	https://chem.nlm.nih.gov/chemidplus/id/0010135894
PubChem	23675776	https://pubchem.ncbi.nlm.nih.gov/compound/23675776
SureChEMBL	SCHEMBL11626626	https://www.surechembl.org/chemical/SCHEMBL11626626
Wikidata	Q27292401

PubMed

Title	Date	PubMed
Quantitative determination of trace concentrations of tetracycline and sulfonamide antibiotics in surface water using solid-phase extraction and liquid chromatography/ion trap tandem mass spectrometry.	2004	15317045
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
Sequence analysis and characterization of sulfonamide resistance plasmid pRF-1 from Salmonella enterica serovar Choleraesuis.	2004 Nov	15518878
Serum activity/concentration profiles of a sustained-released formulation of sulphathiazole-trimethoprim (2.5:1) in calves.	2004 Nov 20	15581142
Spectroscopic features of radiolytic intermediates induced in gamma irradiated sulfatiazole: an ESR study.	2004 Nov 5	15488674
Determination of sulfonamide residues in the tissues of food animals using automated precolumn derivatization and liquid chromatography with fluorescence detection.	2004 Sep-Oct	15493686
Enumeration and antibiotic resistance patterns of fecal indicator organisms isolated from migratory Canada geese (Branta canadensis).	2005 Apr	16107668
Water adsorption kinetics and contact angles of pharmaceutical powders.	2005 Apr	15736196
Flow-through sensor with Fourier transform Raman detection for determination of sulfonamides.	2005 Dec	16284660
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
Aging and microwave effects on alginate/chitosan matrices.	2005 Jun 2	15911046
[Nuclease biosynthesis and growth of Serratia marcescens in the presence of 2-(p-aminobenzenesulfonamide)-thiazole].	2005 May-Jun	16119850
Characterization of polymorphic solid-state changes using variable temperature X-ray powder diffraction.	2005 Sep 1	16085131
Analysis of Pneumocystis jirovecii DHPS alleles implicated in sulfamethoxazole resistance using an Escherichia coli model system.	2005 Spring	15770087
Synthesis, characterization, and biotoxicity of N N donor sulphonamide imine silicon(IV) complexes.	2006	17496998
Evaluation of changes in antimicrobial susceptibility patterns of Pasteurella multocida subsp multocida isolates from pigs in Spain in 1987-1988 and 2003-2004.	2006 Apr	16579760
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
Antibacterial, antifungal and cytotoxic properties of novel N-substituted sulfonamides from 4-hydroxycoumarin.	2006 Dec	17252948
Changes in antibacterial activity of triclosan and sulfa drugs due to photochemical transformations.	2006 Jun	16764465
Influence of endotoxin induced fever on the pharmacokinetics of intramuscularly administered cefepime in rabbits.	2006 Jun	16645340
Dissecting the behavior of a promiscuous solvate former.	2006 Mar 20	16493716
Polymorph farming of acetaminophen and sulfathiazole on a chip.	2006 Nov	16969701
Characterization of temperature-induced phase transitions in five polymorphic forms of sulfathiazole by terahertz pulsed spectroscopy and differential scanning calorimetry.	2006 Nov	16892211
Antibiotic Transport via Runoff and Soil Loss.	2006 Nov-Dec	17071896
14N nuclear quadrupole resonance of some sulfa drugs.	2006 Sep	16621467
Exhaustive extraction of sulfonamide antibiotics from aged agricultural soils using pressurized liquid extraction.	2006 Sep 22	16828782
Assessment of biofilm cell removal and killing and biocide efficacy using the microtiter plate test.	2007	17453732
Aquatic toxicity of acetaminophen, carbamazepine, cimetidine, diltiazem and six major sulfonamides, and their potential ecological risks in Korea.	2007 Apr	17223195
Influence of ethanolic extract of Jasminum grandflorum linn flower on wound healing activity in rats.	2007 Apr-Jun	18175666
Pressurized liquid extraction combined with capillary electrophoresis-mass spectrometry as an improved methodology for the determination of sulfonamide residues in meat.	2007 Aug 3	17433345
Performance of blue-yellow screening test for antimicrobial detection in ovine milk.	2007 Dec	18024727
A longitudinal study of Salmonella shedding and antimicrobial resistance patterns in North Dakota feedlot cattle.	2007 Feb	17340886
Solubility measurement of polymorphic compounds via the pH-metric titration technique.	2007 Feb 7	17049191
Sorption of the veterinary antimicrobial sulfathiazole to organic materials of different origin.	2007 Jan 1	17265938
Determination of sulfonamide compounds in sewage and river by mixed hemimicelles solid-phase extraction prior to liquid chromatography-spectrophotometry.	2007 Jan 19	17137586
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
Time and pH-dependent sorption of the veterinary antimicrobial sulfathiazole to clay minerals and ferrihydrite.	2007 Jul	17350665
Structural analysis of photo-degradation in thiazole-containing compounds by LC-MS/MS and NMR.	2007 Jul 27	17442527
Determination of sulfonamides in milk after precolumn derivatisation by micellar liquid chromatography.	2007 Jun 19	17543601
Evaluation of carbon nanotubes as a solid-phase extraction adsorbent for the extraction of cephalosporins antibiotics, sulfonamides and phenolic compounds from aqueous solution.	2007 Jun 26	17560389
Determination of 10 sulfonamide residues in meat samples by liquid chromatography with ultraviolet detection.	2007 Mar-Apr	17474530
Depth distribution of sulfonamide antibiotics in pore water of an undisturbed loamy grassland soil.	2007 Mar-Apr	17332263
Crystal polymorphism of pharmaceuticals: probing crystal nucleation at the molecular level.	2007 Oct	18035822
Rapid simultaneous determination of 14 sulfonamides in wastewater by liquid chromatography tandem mass spectrometry.	2007 Oct	17763515
[Simultaneous determination of nine sulfonamide residues in milk using solid phase extraction and high performance liquid chromatography].	2007 Sep	18161327
Flow-through optosensor combined with photochemically induced fluorescence for simultaneous determination of binary mixtures of sulfonamides in pharmaceuticals, milk and urine.	2007 Sep 26	17903479
Immunochemical assays for direct sulfonamide antibiotic detection in milk and hair samples using antibody derivatized magnetic nanoparticles.	2008 Feb 13	18177003
The use of sulfathiazole in the treatment of subacute and chronic osteomyelitis : Frank D. Dickson MD (1882-1964), Rex L. Diveley MD, Richard Kiene MD. The 4th president of the AAOS 1935 (FDD).	2008 Jan	18196371
Environmental levels of ultraviolet light potentiate the toxicity of sulfonamide antibiotics in Daphnia magna.	2008 Jan	17940867

Patents

Sample Use Guides

In Vivo Use Guide

Adult: Cream (Sulphathiazole 34.2 mg/g, sulphacetamide 28.6 mg/g, sulphabenzamide 37 mg/g and urea 6.4 mg/g): 5g is applied intra-vaginally bid for 4 to 6 days. Thereafter the dosage may be reduced to one-half or one-quarter.

Route of Administration: Topical

In Vitro Use Guide

25 ug/ml of Sulfathiazole is required for inhibition of in vitro cellulose digestion and volatile fatty acid production by ruminal microorganisms.

Name

Type

Language

SULFATHIAZOLE

Official Name

English

SULFATHIAZOLE [VANDF]

Common Name

English

SULFATHIAZOLE [ORANGE BOOK]

Common Name

English

SULFATHIAZOLE [EP MONOGRAPH]

Common Name

English

SULFATHIAZOLE [GREEN BOOK]

Common Name

English

Sulfathiazole [WHO-DD]

Common Name

English

TRIPLE SULFA (SULFATHIAZOLE)

Common Name

English

SULPHATHIAZOLE

Common Name

English

SULFATHIAZOLE COMPONENT OF TRYSUL

Common Name

English

TRIPLE SULFA (SULFATHIAZOLE) [ORANGE BOOK]

Common Name

English

N(SUP 1)-2-THIAZOLYLSULFANILAMIDE

Systematic Name

English

VAGILIA COMPONENT SULFATHIAZOLE

Common Name

English

SULFATHIAZOLE [USP MONOGRAPH]

Common Name

English

SULFATHIAZOLE COMPONENT OF SULTRIN

Common Name

English

TRYSUL COMPONENT SULFATHIAZOLE

Common Name

English

SULFATHIAZOLE [HSDB]

Common Name

English

SULFATHIAZOLE COMPONENT OF GYNE-SULF

Common Name

English

NSC-683531

Code

English

SULTRIN COMPONENT SULFATHIAZOLE

Common Name

English

SULFATHIAZOLE [MART.]

Common Name

English

sulfathiazole [INN]

Common Name

English

GYNE-SULF COMPONENT SULFATHIAZOLE

Common Name

English

BENZENESULFONAMIDE, 4-AMINO-N-2-THIAZOLYL-

Systematic Name

English

SULFATHIAZOLE [MI]

Common Name

English

NSC-31812

Code

English

SULFATHIAZOLE [USP-RS]

Common Name

English

SULFATHIAZOLE COMPONENT OF VAGILIA

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

77903