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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2017-10-23 19:06:34 UTC
HMDB IDHMDB0015619
Secondary Accession Numbers
  • HMDB15619
Metabolite Identification
Common NameSulfathiazole
DescriptionSulfathiazole is only found in individuals that have used or taken this drug.It is a short-acting sulfa drug. It used to be a common oral and topical antimicrobial until less toxic alternatives were discovered. It is still occasionally used, sometimes in combination with sulfabenzamide and sulfacetamide.
Structure
Thumb
Synonyms
ValueSource
2-(P-Aminobenzenesulfonamido)thiazoleChEBI
2-(P-Aminobenzenesulphonamido)thiazoleChEBI
2-(Sulfanilylamino)thiazoleChEBI
2-SulfanilamidothiazolChEBI
2-SulfanilamidothiazoleChEBI
2-SulfonamidothiazoleChEBI
4-amino-N-2-ThiazolylbenzenesulfonamideChEBI
N(1)-2-ThiazolylsulfanilamideChEBI
SulfanilamidothiazoleChEBI
SulfathiazolChEBI
SulfathiazolumChEBI
SulfatiazolChEBI
SulfthiazoleChEBI
SulphathiazoleChEBI
2-(Sulphanilylamino)thiazoleGenerator
2-SulphanilamidothiazolGenerator
2-SulphanilamidothiazoleGenerator
2-SulphonamidothiazoleGenerator
4-amino-N-2-ThiazolylbenzenesulphonamideGenerator
N(1)-2-ThiazolylsulphanilamideGenerator
SulphanilamidothiazoleGenerator
SulphathiazolGenerator
SulphathiazolumGenerator
SulphatiazolGenerator
SulphthiazoleGenerator
Sodium sulfathiazoleHMDB
AlphadolMeSH
NorsulfazoleMeSH
Sulfathiazole, monosodium saltMeSH
Chemical FormulaC9H9N3O2S2
Average Molecular Weight255.317
Monoisotopic Molecular Weight255.013617927
IUPAC Name4-amino-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide
Traditional Namethiazamide
CAS Registry Number72-14-0
SMILES
NC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CS1
InChI Identifier
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)
InChI KeyJNMRHUJNCSQMMB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentAminobenzenesulfonamides
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
  • Benzenesulfonyl group
  • Aniline or substituted anilines
  • Primary aromatic amine
  • Organosulfonic acid amide
  • Azole
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Thiazole
  • Sulfonyl
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point189 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.05HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.92 g/LALOGPS
logP0.88ALOGPS
logP0.98ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.93ChemAxon
pKa (Strongest Basic)2.04ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.08 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.27 m³·mol⁻¹ChemAxon
Polarizability23.96 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9310000000-362c90cbc34ebb5b96b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-1960000000-7ebf58709da8be9d0d9dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0900000000-3d0cdd49066827cafa83View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-f7971b44ce4287715041View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0pb9-2940000000-2d9aef67398dcb851e42View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-5900000000-f03cbf45fd1ef6844beaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4j-9500000000-1d1e5ab23f50f3e1a8efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9100000000-02aff95420f40ac161b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-01ot-9000000000-518c1b2f38e7b707d3d8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-4629341fc578b9d3ca3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0pb9-2950000000-54cf4b489c407b1da7bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-3900000000-d906641906d22ec2d590View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4j-9800000000-f53d35a00a8692390b26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9100000000-7587cac1009d6df32f99View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-01ot-9000000000-38916267be638c54890aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0900000000-886ee9e3260c7b7583cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-67d88e77f2bf9487a1ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0pb9-4980000000-f023f391d35f708b88c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4j-7900000000-b7781621336d485b51d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9200000000-c1ee875d073a3fcaacfbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-f7b98b823e5755424322View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1960000000-d9192bae4b60058d3be6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdi-9100000000-ef96452c43a2c843adaeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-b2d69fef9b223ffc317eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gvk-4890000000-5d5edc4b46d5d1bbc805View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9310000000-89b3a9fe5f952285541cView in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06147 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06147 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06147
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5148
KEGG Compound IDC11169
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulfathiazole
METLIN IDNot Available
PubChem Compound5340
PDB IDYTZ
ChEBI ID9337
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular weight:
57882.48
References
  1. Ji K, Choi K, Lee S, Park S, Khim JS, Jo EH, Choi K, Zhang X, Giesy JP: Effects of sulfathiazole, oxytetracycline and chlortetracycline on steroidogenesis in the human adrenocarcinoma (H295R) cell line and freshwater fish Oryzias latipes. J Hazard Mater. 2010 Oct 15;182(1-3):494-502. doi: 10.1016/j.jhazmat.2010.06.059. Epub 2010 Jun 19. [PubMed:20630653 ]