SULFATHIAZOLE

First approved in 1940

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

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
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 8504
folic acid biosynthetic process 9 Target ID: GO:0046656 Sources: https://www.genome.jp/dbget-bin/www_bget?D07060+D02447	Inhibitor 8504
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 8504
Escherichia coli 82 Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26428163	Inhibitor 8504

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 8583	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 Health Status: unhealthy 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 Health Status: unhealthy 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 Health Status: unhealthy 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 Health Status: unhealthy 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 Health Status: unhealthy 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 Health Status: unhealthy 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 Health Status: unhealthy 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 Health Status: unhealthy 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 Health Status: unhealthy Sources: https://jamanetwork.com/journals/jama/article-abstract/307661

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP2E1 1060 OATP1B1 1079 CYP2A6 879 CYP1A2 2153 OATP1B3 961	UGT1A4 399

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQzNyJ9fQ==	no [IC50 >10 uM]
CYP2A6 911	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQzNyJ9fQ==	no [IC50 >10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQzNyJ9fQ==	no [IC50 >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQzNyJ9fQ==	no [IC50 >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMNDM3In19	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQzNyJ9fQ==	no [IC50 >10 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMNDM3In19	no [IC50 >10 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQzNyJ9fQ==	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQzNyJ9fQ==	yes [Inhibition 10 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
UGT1A4 399	substrate 4014 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjE5IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQzNyJ9fQ==	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMNDM3In19

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
Concomitant polymorphism in confined environment.	2008-04	17896099
Immunochemical assays for direct sulfonamide antibiotic detection in milk and hair samples using antibody derivatized magnetic nanoparticles.	2008-02-13	18177003
Influence of ethanolic extract of Jasminum grandflorum linn flower on wound healing activity in rats.	2008-01-08	18175666
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).	2008-01	18196371
Environmental levels of ultraviolet light potentiate the toxicity of sulfonamide antibiotics in Daphnia magna.	2008-01	17940867
Performance of blue-yellow screening test for antimicrobial detection in ovine milk.	2007-12	18024727
Simultaneous determination of different classes of antibiotics in fish and livestock by CE-MS.	2007-11	17932875
Determination of sulphonamides in animal tissues by high performance liquid chromatography with pre-column derivatization of 9-fluorenylmethyl chloroformate.	2007-11	17868178
Crystal polymorphism of pharmaceuticals: probing crystal nucleation at the molecular level.	2007-10	18035822
Rapid simultaneous determination of 14 sulfonamides in wastewater by liquid chromatography tandem mass spectrometry.	2007-10	17763515
Flow-through optosensor combined with photochemically induced fluorescence for simultaneous determination of binary mixtures of sulfonamides in pharmaceuticals, milk and urine.	2007-09-26	17903479
[Simultaneous determination of nine sulfonamide residues in milk using solid phase extraction and high performance liquid chromatography].	2007-09	18161327
Pressurized liquid extraction combined with capillary electrophoresis-mass spectrometry as an improved methodology for the determination of sulfonamide residues in meat.	2007-08-03	17433345
Evaluation of the compaction of sulfathiazole polymorphs.	2007-08	17565752
Structural analysis of photo-degradation in thiazole-containing compounds by LC-MS/MS and NMR.	2007-07-27	17442527
Time and pH-dependent sorption of the veterinary antimicrobial sulfathiazole to clay minerals and ferrihydrite.	2007-07	17350665
Evaluation of carbon nanotubes as a solid-phase extraction adsorbent for the extraction of cephalosporins antibiotics, sulfonamides and phenolic compounds from aqueous solution.	2007-06-26	17560389
Determination of sulfonamides in milk after precolumn derivatisation by micellar liquid chromatography.	2007-06-19	17543601
Determination of 10 sulfonamide residues in meat samples by liquid chromatography with ultraviolet detection.	2007-05-04	17474530
Aquatic toxicity of acetaminophen, carbamazepine, cimetidine, diltiazem and six major sulfonamides, and their potential ecological risks in Korea.	2007-04	17223195
Simultaneous determination of 17 sulfonamides and the potentiators ormetoprim and trimethoprim in salmon muscle by liquid chromatography with tandem mass spectrometry detection.	2007-03-22	17373466
Development of an enzyme-linked immunosorbent assay for seven sulfonamide residues and investigation of matrix effects from different food samples.	2007-03-21	17300200
Depth distribution of sulfonamide antibiotics in pore water of an undisturbed loamy grassland soil.	2007-03-03	17332263
[Determination of 12 sulfonamides in cosmetics by ultra performance liquid chromatography].	2007-03	17580695
Effects of sorbate speciation on sorption of selected sulfonamides in three loamy soils.	2007-02-21	17300155
Solubility measurement of polymorphic compounds via the pH-metric titration technique.	2007-02-07	17049191
A longitudinal study of Salmonella shedding and antimicrobial resistance patterns in North Dakota feedlot cattle.	2007-02	17340886
Determination of sulfonamide compounds in sewage and river by mixed hemimicelles solid-phase extraction prior to liquid chromatography-spectrophotometry.	2007-01-19	17137586
Sorption of the veterinary antimicrobial sulfathiazole to organic materials of different origin.	2007-01-01	17265938
Assessment of biofilm cell removal and killing and biocide efficacy using the microtiter plate test.	2007	17453732
Antibacterial, antifungal and cytotoxic properties of novel N-substituted sulfonamides from 4-hydroxycoumarin.	2006-12	17252948
Polymorph farming of acetaminophen and sulfathiazole on a chip.	2006-11	16969701
Characterization of temperature-induced phase transitions in five polymorphic forms of sulfathiazole by terahertz pulsed spectroscopy and differential scanning calorimetry.	2006-11	16892211
Toxicity and biodegradability of sulfonamides and products of their photocatalytic degradation in aqueous solutions.	2006-11	16750553
Antibiotic Transport via Runoff and Soil Loss.	2006-10-31	17071896
Determination of antimicrobials in sludge from infiltration basins at two artificial recharge plants by pressurized liquid extraction-liquid chromatography-tandem mass spectrometry.	2006-10-13	16822516
Exhaustive extraction of sulfonamide antibiotics from aged agricultural soils using pressurized liquid extraction.	2006-09-22	16828782
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.	2006-09-15	16820156
14N nuclear quadrupole resonance of some sulfa drugs.	2006-09	16621467
Multiresidue determination of sulfonamides in edible catfish, shrimp and salmon tissues by high-performance liquid chromatography with postcolumn derivatization and fluorescence detection.	2006-08-18	16750659
A comparison of morphology and surface energy characteristics of sulfathiazole polymorphs based upon single particle studies.	2006-07	16713199
Hapten synthesis and development of polyclonal antibody-based multi-sulfonamide immunoassays.	2006-06-28	16786990
Changes in antibacterial activity of triclosan and sulfa drugs due to photochemical transformations.	2006-06	16764465
Influence of endotoxin induced fever on the pharmacokinetics of intramuscularly administered cefepime in rabbits.	2006-06	16645340
Evaluation of wound healing activity of Allamanda cathartica. L. and Laurus nobilis. L. extracts on rats.	2006-04-05	16597335
Evaluation of changes in antimicrobial susceptibility patterns of Pasteurella multocida subsp multocida isolates from pigs in Spain in 1987-1988 and 2003-2004.	2006-04	16579760
Dissecting the behavior of a promiscuous solvate former.	2006-03-20	16493716
Variations in gene organization and DNA uptake signal sequence in the folP region between commensal and pathogenic Neisseria species.	2006-02-17	16503987
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.	2006-01-03	16385979
Synthesis, characterization, and biotoxicity of N N donor sulphonamide imine silicon(IV) complexes.	2006	17496998

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 `Mon Mar 31 17:35:51 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:51 GMT 2025`
Record UNII	Y7FKS2XWQH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SULFATHIAZOLE

Official Name

English

GYNE-SULF COMPONENT SULFATHIAZOLE

Preferred 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

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

TRYSUL COMPONENT SULFATHIAZOLE

Common Name

English

SULFATHIAZOLE [HSDB]

Common Name

English

NSC-683531

Code

English

SULTRIN COMPONENT SULFATHIAZOLE

Common Name

English

SULFATHIAZOLE [MART.]

Common Name

English

sulfathiazole [INN]

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

Classification Tree Code System Code

EPA PESTICIDE CODE

77903