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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2016-02-11 01:31:07 UTC
HMDB IDHMDB15028
Secondary Accession NumbersNone
Metabolite Identification
Common NameSulfapyridine
DescriptionSulfapyridine is only found in individuals that have used or taken this drug. It is an antibacterial, potentially toxic, used to treat certain skin diseases. [PubChem] Sulfapyridine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid by means of processing the substrate para-aminobenzoic acid (PABA). Dihydropteroate synthetase activity is vital in the synthesis of folate, and folate is required for cells to make nucleic acids, such as DNA or RNA. So if DNA molecules cannot be built, the cell cannot divide.
Structure
Thumb
Synonyms
ValueSource
2-(P-Aminobenzenesulphonamido)pyridineChEBI
2-SulfanilamidopyridinChEBI
2-SulfanilamidopyridineChEBI
2-SulfanilylaminopyridineChEBI
2-SulfapyridineChEBI
4-(2-Pyridinylsulfonyl)anilineChEBI
4-[(2-pyridylamino)Sulfonyl]anilineChEBI
4-amino-N,2-PyridinylbenzenesulfonamideChEBI
4-amino-N-Pyridin-2-yl-benzenesulfonamideChEBI
N-2-PyridylsulfanilamideChEBI
N(1)-2-PyridylsulfanilamideChEBI
N(1)-PyridylsulfanilamideChEBI
SolfapiridinaChEBI
SulfapiridinaChEBI
SulfapyridinumChEBI
SulphapyridineChEBI
2-(P-Aminobenzenesulfonamido)pyridineGenerator
2-SulphanilamidopyridinGenerator
2-SulphanilamidopyridineGenerator
2-SulphanilylaminopyridineGenerator
2-SulphapyridineGenerator
4-(2-Pyridinylsulphonyl)anilineGenerator
4-[(2-pyridylamino)Sulphonyl]anilineGenerator
4-amino-N,2-PyridinylbenzenesulphonamideGenerator
4-amino-N-Pyridin-2-yl-benzenesulphonamideGenerator
N-2-PyridylsulphanilamideGenerator
N(1)-2-PyridylsulphanilamideGenerator
N(1)-PyridylsulphanilamideGenerator
SulphapiridinaGenerator
SulphapyridinumGenerator
N1-2-PyridylsulfanilamideHMDB
Chemical FormulaC11H11N3O2S
Average Molecular Weight249.289
Monoisotopic Molecular Weight249.057197301
IUPAC Name4-amino-N-(pyridin-2-yl)benzene-1-sulfonamide
Traditional Nameronin
CAS Registry Number144-83-2
SMILES
NC1=CC=C(C=C1)S(=O)(=O)NC1=CC=CC=N1
InChI Identifier
InChI=1S/C11H11N3O2S/c12-9-4-6-10(7-5-9)17(15,16)14-11-3-1-2-8-13-11/h1-8H,12H2,(H,13,14)
InChI KeyInChIKey=GECHUMIMRBOMGK-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
  • Aminopyridine
  • Imidolactam
  • Pyridine
  • Primary aromatic amine
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • 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
  • Anti-Infectives
  • Dermatitis herpetiformis suppressant
  • Dermatologic Agents
  • Sulfonamides
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point192 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.35e-01 g/LNot Available
LogP0.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.23 mg/mLALOGPS
logP0.84ALOGPS
logP1.01ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.24ChemAxon
pKa (Strongest Basic)2.63ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.08 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity65.75 m3·mol-1ChemAxon
Polarizability24.97 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 DB00891
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00891
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00891
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5145
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulfapyridine
NuGOwiki LinkHMDB15028
Metagene LinkHMDB15028
METLIN IDNot Available
PubChem Compound5336
PDB IDNot Available
ChEBI ID132842
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. [19934256 ]