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

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
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
Sensitive spectrophotometric determination of nitrite in human saliva and rain water and of nitrogen dioxide in the atmosphere.	2001 Jan-Feb	11234852
Characterization of dextran-producing Leuconostoc strains.	2001 Mar	11264750
Low-level determination of polymorph composition in physical mixtures by near-infrared reflectance spectroscopy.	2001 Mar	11170029
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
Quantification of veterinary antibiotics (sulfonamides and trimethoprim) in animal manure by liquid chromatography-mass spectrometry.	2002 Apr 5	12064522
Drug release properties of pectinate microspheres prepared by emulsification method.	2002 Aug 21	12176253
Liquid chromatographic determination of multiple sulfonamides, nitrofurans, and chloramphenicol residues in pasteurized milk.	2002 Jan-Feb	11878601
Release characteristics of pectin microspheres prepared by an emulsification technique.	2002 Jul-Aug	12396387
A new, sensitive, and rapid spectrophotometric method for the determination of sulfa drugs.	2002 Jul-Aug	12180680
Face specific surface properties of pharmaceutical crystals.	2002 Jun	12115843
Drug-plasma protein binding assay by electrokinetic chromatography-frontal analysis.	2002 Mar	11920882
Iminodibenzyl as a novel coupling agent for the spectrophotometric determination of sulfonamide derivatives.	2002 Mar	11880002
Application of time-dependent sessile drop contact angles on compacts to characterise the surface energetics of sulfathiazole crystals.	2002 Mar 2	11839436
Quantitative determination of trace concentrations of tetracycline and sulfonamide antibiotics in surface water using solid-phase extraction and liquid chromatography/ion trap tandem mass spectrometry.	2004	15317045
Validation of a confirmatory method for the determination of sulphonamides in muscle according to the European Union regulation 2002/657/EC.	2004 Apr 2	15065772
Quantitative analysis of twelve sulfonamides in honey after acidic hydrolysis by high-performance liquid chromatography with post-column derivatization and fluorescence detection.	2004 Aug 20	15481463
Photochemical fate of sulfa drugs in the aquatic environment: sulfa drugs containing five-membered heterocyclic groups.	2004 Jul 15	15298203
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
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
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	16579760
Evaluation of wound healing activity of Allamanda cathartica. L. and Laurus nobilis. L. extracts on rats.	2006 Apr 5	16597335
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
Changes in antibacterial activity of triclosan and sulfa drugs due to photochemical transformations.	2006 Jun	16764465
Hapten synthesis and development of polyclonal antibody-based multi-sulfonamide immunoassays.	2006 Jun 28	16786990
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
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
Performance of blue-yellow screening test for antimicrobial detection in ovine milk.	2007 Dec	18024727
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
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
Determination of sulphonamides in animal tissues by high performance liquid chromatography with pre-column derivatization of 9-fluorenylmethyl chloroformate.	2007 Nov	17868178
[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
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

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

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