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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2021-10-13 05:51:36 UTC
HMDB IDHMDB0015506
Secondary Accession Numbers
  • HMDB15506
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
Data?1582753304
Synonyms
ValueSource
3-(Phenylazo)-2,6-pyridinediamineKegg
FenazopiridinaKegg
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 KeyQPFYXYFORQJZEC-FOCLMDBBSA-N
Chemical Taxonomy
Description 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
  • Dihydropyridine
  • Monocyclic benzene moiety
  • Hydropyridine
  • Benzenoid
  • Imidolactam
  • Heteroaromatic compound
  • Azo compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Azacycle
  • Primary amine
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point139 °CNot Available
Boiling Point240.00 to 241.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.2 g/LNot Available
LogP5.301 (est)The Good Scents Company Information System
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
AllCCS[M+H]+Not Available147.786http://allccs.zhulab.cn/database/detail?ID=AllCCS00000949
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP10(2.31) g/LALOGPS
logP10(2.69) g/LChemAxon
logS10(-3) g/LALOGPS
pKa (Strongest Acidic)18.85ChemAxon
pKa (Strongest Basic)6.86ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.65 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.25 m³·mol⁻¹ChemAxon
Polarizability22.66 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phenazopyridine GC-MS (Non-derivatized) - 70eV, Positivesplash10-090a-2910000000-d9ed55f7a6e317efe1722017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenazopyridine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenazopyridine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenazopyridine LC-ESI-QQ , positive-QTOFsplash10-03di-3790000000-b512b9204606a7555a5b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenazopyridine LC-ESI-QQ , positive-QTOFsplash10-03di-2970000000-0b1e342d0932d1b1e5142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenazopyridine LC-ESI-QQ , positive-QTOFsplash10-05fr-4900000000-ca0b4addc8cef352136e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenazopyridine LC-ESI-QQ , positive-QTOFsplash10-053r-9600000000-3269efb012d6f568ca892017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenazopyridine LC-ESI-QQ , positive-QTOFsplash10-003r-9100000000-82c1432637ce4b1cf4f42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenazopyridine LC-ESI-IT , positive-QTOFsplash10-05vk-3920000000-53a0d95ed732abd389e72017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenazopyridine 10V, Positive-QTOFsplash10-03di-1290000000-2b7c613e7803cdc27a9c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenazopyridine 20V, Positive-QTOFsplash10-03dj-5890000000-d9a454007e96e4b89b292016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenazopyridine 40V, Positive-QTOFsplash10-00kf-9200000000-fdbf18b7b730d45827462016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenazopyridine 10V, Negative-QTOFsplash10-03di-2290000000-401556bb3c3ea86e22822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenazopyridine 20V, Negative-QTOFsplash10-03kc-5960000000-2d0e0d936cb6b59301c12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenazopyridine 40V, Negative-QTOFsplash10-0006-9200000000-4cbbd556449aafe83cba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenazopyridine 10V, Positive-QTOFsplash10-03di-0090000000-36fa26cf92b7f44a3ce62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenazopyridine 20V, Positive-QTOFsplash10-03di-0190000000-ae69ddf6f699b7f276b42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenazopyridine 40V, Positive-QTOFsplash10-01di-7900000000-29cf686a8c802275194d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenazopyridine 10V, Negative-QTOFsplash10-03di-0090000000-30d0b34fa4acc6bca2902021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenazopyridine 20V, Negative-QTOFsplash10-03di-0690000000-6544fbf31bee0d9145af2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenazopyridine 40V, Negative-QTOFsplash10-0006-9300000000-eb0884bec9d838ae22202021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01438 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01438 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01438
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4592
KEGG Compound IDC07429
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenazopyridine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID331062
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1447201
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. [PubMed: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. doi: 10.1002/nau.20886. [PubMed:20976818 ]