SUCCINYLSULFATHIAZOLE

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H13N3O5S2
Molecular Weight	355.389
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=SKVLYVHULOWXTD-UHFFFAOYSA-N

InChI=1S/C13H13N3O5S2/c17-11(5-6-12(18)19)15-9-1-3-10(4-2-9)23(20,21)16-13-14-7-8-22-13/h1-4,7-8H,5-6H2,(H,14,16)(H,15,17)(H,18,19)

HIDE SMILES / InChI

Molecular Formula	C13H13N3O5S2
Molecular Weight	355.389
Charge	0
Count

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

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
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
Water adsorption kinetics and contact angles of pharmaceutical powders.	2005 Apr	15736196
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
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
Confirmation of sulfamethazine, sulfathiazole, and sulfadimethoxine residues in condensed milk and soft-cheese products by liquid chromatography/tandem mass spectrometry.	2005 May-Jun	16001847
Vitamin B3 confers resistance to sulfa drugs in Saccharomyces cerevisiae.	2005 Oct 1	16112818
Controlled release from triple layer, donut-shaped tablets with enteric polymers.	2005 Oct 22	16354001
Characterization of polymorphic solid-state changes using variable temperature X-ray powder diffraction.	2005 Sep 1	16085131
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.	2005 Sep-Oct	16385979
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
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
A comparison of morphology and surface energy characteristics of sulfathiazole polymorphs based upon single particle studies.	2006 Jul	16713199
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
Hapten synthesis and development of polyclonal antibody-based multi-sulfonamide immunoassays.	2006 Jun 28	16786990
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
Toxicity and biodegradability of sulfonamides and products of their photocatalytic degradation in aqueous solutions.	2006 Nov	16750553
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
14N nuclear quadrupole resonance of some sulfa drugs.	2006 Sep	16621467
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
Exhaustive extraction of sulfonamide antibiotics from aged agricultural soils using pressurized liquid extraction.	2006 Sep 22	16828782
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
Effects of sorbate speciation on sorption of selected sulfonamides in three loamy soils.	2007 Feb 21	17300155
Sorption of the veterinary antimicrobial sulfathiazole to organic materials of different origin.	2007 Jan 1	17265938
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
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
Development of an enzyme-linked immunosorbent assay for seven sulfonamide residues and investigation of matrix effects from different food samples.	2007 Mar 21	17300200
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
Simultaneous determination of different classes of antibiotics in fish and livestock by CE-MS.	2007 Nov	17932875
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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:24:47 UTC 2023` Edited by `admin` on `Sat Dec 16 16:24:47 UTC 2023`
Record UNII	RSS8647O4S
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SUCCINYLSULFATHIAZOLE

Official Name

English

CREMOSUXIDINE

Brand Name

English

KAOXIDINE

Brand Name

English

SULFASUXIDINE

Brand Name

English

SUCCINYLSULFATHIAZOLE [EP IMPURITY]

Common Name

English

succinylsulfathiazole [INN]

Common Name

English

SUCCINYL SULFATHIAZOLE

Common Name

English

GUANICAR

Brand Name

English

COLISTATIN

Brand Name

English

Succinylsulfathiazole [WHO-DD]

Common Name

English

NSC-163939

Code

English

SULFADIGESIN

Brand Name

English

SUCCINYLSULFATHIAZOLE [MART.]

Common Name

English

THIACYL

Brand Name

English

4-OXO-4-((4-((2-THIAZOLYLAMINO)SULFONYL)PHENYL)AMINO)BUTANOIC ACID

Systematic Name

English

NSC-14193

Code

English

SUCCINYLSULFATHIAZOLE [MI]

Common Name

English

SULFASUCCIDINE

Brand Name

English

KAOXIDIN

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29739