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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:33:37 UTC
HMDB IDHMDB15619
Secondary Accession NumbersNone
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
SulphathiazoleChEBI
2-(Sulphanilylamino)thiazoleGenerator
2-SulphanilamidothiazolGenerator
2-SulphanilamidothiazoleGenerator
2-SulphonamidothiazoleGenerator
4-amino-N-2-ThiazolylbenzenesulphonamideGenerator
N(1)-2-ThiazolylsulphanilamideGenerator
SulphanilamidothiazoleGenerator
SulphathiazolGenerator
SulphathiazolumGenerator
SulphatiazolGenerator
Sodium sulfathiazoleHMDB
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 KeyInChIKey=JNMRHUJNCSQMMB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentAminobenzenesulfonamides
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
  • Sulfonylaniline
  • Substituted aniline
  • Aniline
  • Primary aromatic amine
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Thiazole
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Azole
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-Infective Agents
Application
  • Pharmaceutical
Cellular locations
  • Membrane
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.27 m3·mol-1ChemAxon
Polarizability23.96 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06147
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06147
  • Not Applicable
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
NuGOwiki LinkHMDB15619
Metagene LinkHMDB15619
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. Epub 2010 Jun 19. [20630653 ]