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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-03-02 21:33:37 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
SulphapyridinMeSH
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 KeyGECHUMIMRBOMGK-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
  • Pyridine
  • Organosulfonic acid amide
  • Imidolactam
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Azacycle
  • Organic oxide
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • 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
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a59-4920000000-ddd28eca3499faaddfb1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0900000000-76404b7958aaaddb00c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-b794dcd70eedfd04a9e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-1690000000-d32f010faae95dd6e5ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-3900000000-b89b3d587bf8893e343aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4l-7900000000-e9c1ce1a2bfb8587016bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-052f-9600000000-c2b3b96e2d3db5fc940fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05mo-9400000000-6eeb6714b222ec20731eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-14bd7d3423dbbc1677f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-1690000000-ec5ad1677ec436c15076View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-3900000000-3221fbcec55c511e58a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-7900000000-4959721f5e57ee1708c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-052f-9600000000-cb7f712bbbba5e75ed73View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05mo-9400000000-542a7f83b7c124aeaa3bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a59-0900000000-ebce9cc4e8380518ddecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4l-5900000000-c36697c8e5b4522ccfc5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-052f-9600000000-07faf61cc06e82c703a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0900000000-2ae47a77fd32fcf2200eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a59-0900000000-4653688bc5b5c91f5a27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00891 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00891 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]