SULFATHIAZOLE SODIUM

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H8N3O2S2.Na
Molecular Weight	277.298
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].NC1=CC=C(C=C1)S(=O)(=O)[N-]C2=NC=CS2

InChI

InChIKey=GWIJGCIVKLITQK-UHFFFAOYSA-N

InChI=1S/C9H8N3O2S2.Na/c10-7-1-3-8(4-2-7)16(13,14)12-9-11-5-6-15-9;/h1-6H,10H2;/q-1;+1

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
[On the antituberculous action of sulphathiazole. II. The effects of sulfathiazole on the morphology of Mycobacterium avium].	1955 Jun	14392707
Determination of the onset of crystallization of N1-2-(thiazolyl)sulfanilamide (sulfathiazole) by UV-Vis and calorimetry using an automated reaction platform; subsequent characterization of polymorphic forms using dispersive Raman spectroscopy.	2001 Aug	11506030
Characterization of dextran-producing Leuconostoc strains.	2001 Mar	11264750
Polymorph control of sulfathiazole in supercritical CO2.	2001 May	11465426
Molecular epidemiology of Salmonella Heidelberg in an equine hospital.	2001 May 3	11278126
Estimating the relative stability of polymorphs and hydrates from heats of solution and solubility data.	2001 Sep	11745780
Nuclease activity of [Cu(sulfathiazolato)(2)(benzimidazole)(2)]2MeOH. Synthesis, properties and crystal structure.	2002 Apr 10	11931960
Drug release properties of pectinate microspheres prepared by emulsification method.	2002 Aug 21	12176253
Face specific surface properties of pharmaceutical crystals.	2002 Jun	12115843
Determination of sulfathiazole in type C medicated swine feed by reversed-phase liquid chromatography with post-column derivatization.	2003 Jul-Aug	14509417
Specific polyclonal-based immunoassays for sulfathiazole.	2004 Aug	15221195
Routine monitoring of antibiotics in water and wastewater with a radioimmunoassay technique.	2004 Aug-Sep	15276731
Over-production of dihydrofolate reductase leads to sulfa-dihydropteroate resistance in yeast.	2004 Jul 15	15251211
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
Evaluating the biodegradability of sulfamethazine, sulfamethoxazole, sulfathiazole, and trimethoprim at different stages of sewage treatment.	2005 Jun	16117111
Determination of sulphathiazole and sulphanilamide by photochemically induced fluorescence and first-derivative fluorescence.	2005 Jun 15	15925230
Aging and microwave effects on alginate/chitosan matrices.	2005 Jun 2	15911046
On the mechanism of solubilization of drugs in the presence of poorly soluble additives.	2005 May 13	15848002
[Nuclease biosynthesis and growth of Serratia marcescens in the presence of 2-(p-aminobenzenesulfonamide)-thiazole].	2005 May-Jun	16119850
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.	2005 Sep-Oct	16385979
Antibacterial, antifungal and cytotoxic properties of novel N-substituted sulfonamides from 4-hydroxycoumarin.	2006 Dec	17252948
Variations in gene organization and DNA uptake signal sequence in the folP region between commensal and pathogenic Neisseria species.	2006 Feb 17	16503987
Changes in antibacterial activity of triclosan and sulfa drugs due to photochemical transformations.	2006 Jun	16764465
Dissecting the behavior of a promiscuous solvate former.	2006 Mar 20	16493716
Characterization of temperature-induced phase transitions in five polymorphic forms of sulfathiazole by terahertz pulsed spectroscopy and differential scanning calorimetry.	2006 Nov	16892211
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
Multiwalled carbon nanotubes as sorbent for on-line coupling of solid-phase extraction to high-performance liquid chromatography for simultaneous determination of 10 sulfonamides in eggs and pork.	2006 Sep 15	16820156
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
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
Depth distribution of sulfonamide antibiotics in pore water of an undisturbed loamy grassland soil.	2007 Mar-Apr	17332263
Simultaneous determination of different classes of antibiotics in fish and livestock by CE-MS.	2007 Nov	17932875
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
Immunochemical assays for direct sulfonamide antibiotic detection in milk and hair samples using antibody derivatized magnetic nanoparticles.	2008 Feb 13	18177003

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 SODIUM

Common Name

English

SULFATHIAZOLE SODIUM [MART.]

Common Name

English

SODIUM SULFATHIAZOLE

Common Name

English

Sulfathiazole sodium [WHO-DD]

Common Name

English

Code System Code Type Description

DRUG BANK

DBSALT000848