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Details

Stereochemistry ACHIRAL
Molecular Formula C9H8N3O2S2.Na.5H2O
Molecular Weight 367.375
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULPHATHIAZOLE SODIUM PENTAHYDRATE

SMILES

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

InChI

InChIKey=NKCXOSYACXARER-UHFFFAOYSA-N
InChI=1S/C9H8N3O2S2.Na.5H2O/c10-7-1-3-8(4-2-7)16(13,14)12-9-11-5-6-15-9;;;;;;/h1-6H,10H2;;5*1H2/q-1;+1;;;;;

HIDE SMILES / InChI

Description
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

Curator's Comment: Introduced as Tiazol by C. and C. https://books.google.ru/books?id=_J2ti4EkYpkC&pg=PA3112&lpg=PA3112&dq=sulfathiazole retrieved from Pharmaceutical Manufacturing Encyclopedia, 3rd Edition William Andrew Publishing, p.3112

Approval Year

Doses

Doses

DosePopulationAdverse 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:
unhealthy
n = 100
Health Status: unhealthy
Condition: infection
Population Size: 100
Sources:
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:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy
n = 100
Health Status: unhealthy
Condition: infection
Population Size: 100
Sources:
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:
unhealthy
n = 100
Health Status: unhealthy
Condition: infection
Population Size: 100
Sources:
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:
unhealthy
n = 100
Health Status: unhealthy
Condition: infection
Population Size: 100
Sources:
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:
unhealthy
n = 100
Health Status: unhealthy
Condition: infection
Population Size: 100
Sources:
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:
unhealthy
n = 100
Health Status: unhealthy
Condition: infection
Population Size: 100
Sources:
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:
unhealthy
n = 100
Health Status: unhealthy
Condition: infection
Population Size: 100
Sources:
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:
unhealthy
n = 100
Health Status: unhealthy
Condition: infection
Population Size: 100
Sources:
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:
unhealthy
n = 100
Health Status: unhealthy
Condition: infection
Population Size: 100
Sources:
PubMed

PubMed

TitleDatePubMed
Enumeration and antibiotic resistance patterns of fecal indicator organisms isolated from migratory Canada geese (Branta canadensis).
2005 Apr
Evaluating the biodegradability of sulfamethazine, sulfamethoxazole, sulfathiazole, and trimethoprim at different stages of sewage treatment.
2005 Jun
Vitamin B3 confers resistance to sulfa drugs in Saccharomyces cerevisiae.
2005 Oct 1
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.
2005 Sep-Oct
Synthesis, characterization, and biotoxicity of N N donor sulphonamide imine silicon(IV) complexes.
2006
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
Evaluation of wound healing activity of Allamanda cathartica. L. and Laurus nobilis. L. extracts on rats.
2006 Apr 5
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
Antibacterial, antifungal and cytotoxic properties of novel N-substituted sulfonamides from 4-hydroxycoumarin.
2006 Dec
A comparison of morphology and surface energy characteristics of sulfathiazole polymorphs based upon single particle studies.
2006 Jul
Changes in antibacterial activity of triclosan and sulfa drugs due to photochemical transformations.
2006 Jun
Hapten synthesis and development of polyclonal antibody-based multi-sulfonamide immunoassays.
2006 Jun 28
Polymorph farming of acetaminophen and sulfathiazole on a chip.
2006 Nov
Characterization of temperature-induced phase transitions in five polymorphic forms of sulfathiazole by terahertz pulsed spectroscopy and differential scanning calorimetry.
2006 Nov
Toxicity and biodegradability of sulfonamides and products of their photocatalytic degradation in aqueous solutions.
2006 Nov
Antibiotic Transport via Runoff and Soil Loss.
2006 Nov-Dec
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
14N nuclear quadrupole resonance of some sulfa drugs.
2006 Sep
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
Exhaustive extraction of sulfonamide antibiotics from aged agricultural soils using pressurized liquid extraction.
2006 Sep 22
Assessment of biofilm cell removal and killing and biocide efficacy using the microtiter plate test.
2007
Aquatic toxicity of acetaminophen, carbamazepine, cimetidine, diltiazem and six major sulfonamides, and their potential ecological risks in Korea.
2007 Apr
Influence of ethanolic extract of Jasminum grandflorum linn flower on wound healing activity in rats.
2007 Apr-Jun
Evaluation of the compaction of sulfathiazole polymorphs.
2007 Aug
Pressurized liquid extraction combined with capillary electrophoresis-mass spectrometry as an improved methodology for the determination of sulfonamide residues in meat.
2007 Aug 3
Performance of blue-yellow screening test for antimicrobial detection in ovine milk.
2007 Dec
A longitudinal study of Salmonella shedding and antimicrobial resistance patterns in North Dakota feedlot cattle.
2007 Feb
Effects of sorbate speciation on sorption of selected sulfonamides in three loamy soils.
2007 Feb 21
Solubility measurement of polymorphic compounds via the pH-metric titration technique.
2007 Feb 7
Sorption of the veterinary antimicrobial sulfathiazole to organic materials of different origin.
2007 Jan 1
Determination of sulfonamide compounds in sewage and river by mixed hemimicelles solid-phase extraction prior to liquid chromatography-spectrophotometry.
2007 Jan 19
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
Time and pH-dependent sorption of the veterinary antimicrobial sulfathiazole to clay minerals and ferrihydrite.
2007 Jul
Structural analysis of photo-degradation in thiazole-containing compounds by LC-MS/MS and NMR.
2007 Jul 27
Determination of sulfonamides in milk after precolumn derivatisation by micellar liquid chromatography.
2007 Jun 19
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
[Determination of 12 sulfonamides in cosmetics by ultra performance liquid chromatography].
2007 Mar
Development of an enzyme-linked immunosorbent assay for seven sulfonamide residues and investigation of matrix effects from different food samples.
2007 Mar 21
Determination of 10 sulfonamide residues in meat samples by liquid chromatography with ultraviolet detection.
2007 Mar-Apr
Depth distribution of sulfonamide antibiotics in pore water of an undisturbed loamy grassland soil.
2007 Mar-Apr
Simultaneous determination of different classes of antibiotics in fish and livestock by CE-MS.
2007 Nov
Determination of sulphonamides in animal tissues by high performance liquid chromatography with pre-column derivatization of 9-fluorenylmethyl chloroformate.
2007 Nov
Crystal polymorphism of pharmaceuticals: probing crystal nucleation at the molecular level.
2007 Oct
Rapid simultaneous determination of 14 sulfonamides in wastewater by liquid chromatography tandem mass spectrometry.
2007 Oct
[Simultaneous determination of nine sulfonamide residues in milk using solid phase extraction and high performance liquid chromatography].
2007 Sep
Flow-through optosensor combined with photochemically induced fluorescence for simultaneous determination of binary mixtures of sulfonamides in pharmaceuticals, milk and urine.
2007 Sep 26
Concomitant polymorphism in confined environment.
2008 Apr
Immunochemical assays for direct sulfonamide antibiotic detection in milk and hair samples using antibody derivatized magnetic nanoparticles.
2008 Feb 13
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
Environmental levels of ultraviolet light potentiate the toxicity of sulfonamide antibiotics in Daphnia magna.
2008 Jan
Patents

Sample Use Guides

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
SULPHATHIAZOLE SODIUM PENTAHYDRATE
Common Name English
SODIUM SULFATHIAZOLE PENTAHYDRATE
Common Name English
SULFATHIAZOLE SODIUM PENTAHYDRATE
Common Name English
SULFANILAMIDE, N1-2-THIAZOLYL-, MONOSODIUM SALT, PENTAHYDRATE
Common Name English
BENZENESULFONAMIDE, 4-AMINO-N-2-THIAZOLYL-, MONOSODIUM SALT, PENTAHYDRATE
Common Name English
BENZENESULFONAMIDE, 4-AMINO-N-2-THIAZOLYL-, SODIUM SALT, HYDRATE (1:1:5)
Systematic Name English
Code System Code Type Description
PUBCHEM
76966349
Created by admin on Sat Dec 16 09:41:33 GMT 2023 , Edited by admin on Sat Dec 16 09:41:33 GMT 2023
PRIMARY
FDA UNII
ST7PF0D71H
Created by admin on Sat Dec 16 09:41:33 GMT 2023 , Edited by admin on Sat Dec 16 09:41:33 GMT 2023
PRIMARY
CAS
6791-71-5
Created by admin on Sat Dec 16 09:41:33 GMT 2023 , Edited by admin on Sat Dec 16 09:41:33 GMT 2023
PRIMARY