Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C13H13N3O5S2.H2O |
| Molecular Weight | 373.405 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.OC(=O)CCC(=O)NC1=CC=C(C=C1)S(=O)(=O)NC2=NC=CS2
InChI
InChIKey=QZIZYTCUSHTEBJ-UHFFFAOYSA-N
InChI=1S/C13H13N3O5S2.H2O/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);1H2
DescriptionCurator's Comment: Description was created based on several sources, including http://www.mims.com/india/drug/info/sulfathiazole?type=full&mtype=generic#Indications
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.
Approval Year
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: |
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%) Other AEs:Nausea and vomiting (6%) Nitrogen retention (1%) Sources: Hematuria (1%) Drug fever (2%) Burning eyes (2%) Conjunctival injection (1%) Anemia (1%) |
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: |
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
| Title | Date | PubMed |
|---|---|---|
| Molecular epidemiology of Salmonella Heidelberg in an equine hospital. | 2001 May 3 |
|
| Drug release properties of pectinate microspheres prepared by emulsification method. | 2002 Aug 21 |
|
| Iminodibenzyl as a novel coupling agent for the spectrophotometric determination of sulfonamide derivatives. | 2002 Mar |
|
| Effects of antimicrobials and weaning on porcine serum insulin-like growth factor binding protein levels. | 2003 Jun |
|
| Validation of a confirmatory method for the determination of sulphonamides in muscle according to the European Union regulation 2002/657/EC. | 2004 Apr 2 |
|
| Photochemical fate of sulfa drugs in the aquatic environment: sulfa drugs containing five-membered heterocyclic groups. | 2004 Jul 15 |
|
| 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 |
|
| Controlled release from triple layer, donut-shaped tablets with enteric polymers. | 2005 Oct 22 |
|
| Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry. | 2005 Sep-Oct |
|
| Analysis of Pneumocystis jirovecii DHPS alleles implicated in sulfamethoxazole resistance using an Escherichia coli model system. | 2005 Spring |
|
| Synthesis, characterization, and biotoxicity of N N donor sulphonamide imine silicon(IV) complexes. | 2006 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Crystal polymorphism of pharmaceuticals: probing crystal nucleation at the molecular level. | 2007 Oct |
|
| 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 |
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
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6101-17-3
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8308
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DTXSID10976489
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HM7K18OJZ9
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C009342
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m10278
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PRIMARY | Merck Index |
ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
