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Details

Stereochemistry ACHIRAL
Molecular Formula 2C9H8N3O2S2.Zn
Molecular Weight 574.026
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFATHIAZOLE ZINC

SMILES

[Zn++].NC1=CC=C(C=C1)S(=O)(=O)[N-]C2=NC=CS2.NC3=CC=C(C=C3)S(=O)(=O)[N-]C4=NC=CS4

InChI

InChIKey=BYDMFZFWWZCIFA-UHFFFAOYSA-N
InChI=1S/2C9H8N3O2S2.Zn/c2*10-7-1-3-8(4-2-7)16(13,14)12-9-11-5-6-15-9;/h2*1-6H,10H2;/q2*-1;+2

HIDE SMILES / InChI

Molecular Formula Zn
Molecular Weight 65.409
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C9H9N3O2S2
Molecular Weight 255.317
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Sequence analysis and characterization of sulfonamide resistance plasmid pRF-1 from Salmonella enterica serovar Choleraesuis.
2004 Nov
Serum activity/concentration profiles of a sustained-released formulation of sulphathiazole-trimethoprim (2.5:1) in calves.
2004 Nov 20
Spectroscopic features of radiolytic intermediates induced in gamma irradiated sulfatiazole: an ESR study.
2004 Nov 5
Determination of sulfonamide residues in the tissues of food animals using automated precolumn derivatization and liquid chromatography with fluorescence detection.
2004 Sep-Oct
Enumeration and antibiotic resistance patterns of fecal indicator organisms isolated from migratory Canada geese (Branta canadensis).
2005 Apr
Water adsorption kinetics and contact angles of pharmaceutical powders.
2005 Apr
Evaluating the biodegradability of sulfamethazine, sulfamethoxazole, sulfathiazole, and trimethoprim at different stages of sewage treatment.
2005 Jun
Aging and microwave effects on alginate/chitosan matrices.
2005 Jun 2
On the mechanism of solubilization of drugs in the presence of poorly soluble additives.
2005 May 13
[Nuclease biosynthesis and growth of Serratia marcescens in the presence of 2-(p-aminobenzenesulfonamide)-thiazole].
2005 May-Jun
Confirmation of sulfamethazine, sulfathiazole, and sulfadimethoxine residues in condensed milk and soft-cheese products by liquid chromatography/tandem mass spectrometry.
2005 May-Jun
Vitamin B3 confers resistance to sulfa drugs in Saccharomyces cerevisiae.
2005 Oct 1
Characterization of polymorphic solid-state changes using variable temperature X-ray powder diffraction.
2005 Sep 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
Variations in gene organization and DNA uptake signal sequence in the folP region between commensal and pathogenic Neisseria species.
2006 Feb 17
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
Influence of endotoxin induced fever on the pharmacokinetics of intramuscularly administered cefepime in rabbits.
2006 Jun
Dissecting the behavior of a promiscuous solvate former.
2006 Mar 20
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
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
Assessment of biofilm cell removal and killing and biocide efficacy using the microtiter plate test.
2007
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
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
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
[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
Determination of sulphonamides in animal tissues by high performance liquid chromatography with pre-column derivatization of 9-fluorenylmethyl chloroformate.
2007 Nov
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
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.
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:42:20 UTC 2023
Edited
by admin
on Wed Jul 05 22:42:20 UTC 2023
Record UNII
4KCI0QUF9Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SULFATHIAZOLE ZINC
Common Name English
BENZENESULFONAMIDE, 4-AMINO-N-2-THIAZOLYL-, ZINC SALT
Common Name English
ZINC SULFATHIAZOLE
Common Name English
Code System Code Type Description
FDA UNII
4KCI0QUF9Q
Created by admin on Wed Jul 05 22:42:20 UTC 2023 , Edited by admin on Wed Jul 05 22:42:20 UTC 2023
PRIMARY
PUBCHEM
21571
Created by admin on Wed Jul 05 22:42:20 UTC 2023 , Edited by admin on Wed Jul 05 22:42:20 UTC 2023
PRIMARY
CAS
5434-78-6
Created by admin on Wed Jul 05 22:42:20 UTC 2023 , Edited by admin on Wed Jul 05 22:42:20 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY