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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:33:10 UTC
HMDB IDHMDB15506
Secondary Accession NumbersNone
Metabolite Identification
Common NamePhenazopyridine
DescriptionPhenazopyridine is only found in individuals that have used or taken this drug. It is a local anesthetic that has been used in urinary tract disorders. Its use is limited by problems with toxicity (primarily blood disorders) and potential carcinogenicity. [PubChem]Phenazopyridine's mechanism of action is not well known, and only basic information on its interaction with the body is available. It is known that the chemical has a direct topical analgesic effect on the mucosa lining of the urinary tract.
Structure
Thumb
Synonyms
ValueSource
FenazopiridinaKegg
3-(phenylazo)-2,6-PyridinediamineKegg
PyridacilHMDB
Chemical FormulaC11H11N5
Average Molecular Weight213.2385
Monoisotopic Molecular Weight213.101445377
IUPAC Name3-[(E)-2-phenyldiazen-1-yl]pyridine-2,6-diamine
Traditional Namephenazopyridine
CAS Registry Number94-78-0
SMILES
NC1=NC(N)=C(C=C1)\N=N\C1=CC=CC=C1
InChI Identifier
InChI=1S/C11H11N5/c12-10-7-6-9(11(13)14-10)16-15-8-4-2-1-3-5-8/h1-7H,(H4,12,13,14)/b16-15+
InChI KeyInChIKey=QPFYXYFORQJZEC-FOCLMDBBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminopyridines and derivatives. These are organic heterocyclic compounds containing an amino group attached to a pyridine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassAminopyridines and derivatives
Direct ParentAminopyridines and derivatives
Alternative Parents
Substituents
  • Aminopyridine
  • Imidolactam
  • Benzenoid
  • Primary aromatic amine
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Azo compound
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anesthetics, Local
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point139 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.02e-01 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.2 mg/mLALOGPS
logP2.31ALOGPS
logP2.69ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)18.85ChemAxon
pKa (Strongest Basic)6.86ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.65 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.25 m3·mol-1ChemAxon
Polarizability22.66 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 DB01438
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01438
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01438
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4592
KEGG Compound IDC07429
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenazopyridine
NuGOwiki LinkHMDB15506
Metagene LinkHMDB15506
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID331062
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in ion channel activity
Specific function:
Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient
Gene Name:
SCN1A
Uniprot ID:
P35498
Molecular weight:
228969.5
References
  1. Ragsdale DS, McPhee JC, Scheuer T, Catterall WA: Common molecular determinants of local anesthetic, antiarrhythmic, and anticonvulsant block of voltage-gated Na+ channels. Proc Natl Acad Sci U S A. 1996 Aug 20;93(17):9270-5. [8799190 ]
  2. Aizawa N, Wyndaele JJ: Effects of phenazopyridine on rat bladder primary afferent activity, and comparison with lidocaine and acetaminophen. Neurourol Urodyn. 2010 Nov;29(8):1445-50. [20976818 ]