Welcome to DrugBank 4.0! If you prefer, you can still go back to version 3.0.
Identification
NamePhenazopyridine
Accession NumberDB01438
Typesmall molecule
Groupsapproved
Description

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]

Structure
Thumb
SynonymsNot Available
Salts
Name/CAS Structure Properties
Phenazopyridine hydrochloride
Thumb Not applicable DBSALT000915
Brand names
NameCompany
AZO-StandardNot Available
BaridiumNot Available
PhenazodineNot Available
ProdiumNot Available
PyrazodineNot Available
PyridiateNot Available
PyridiumNot Available
SeduralNot Available
UristatNot Available
UrodineNot Available
UrogesicNot Available
ViridiumNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number94-78-0
WeightAverage: 213.2385
Monoisotopic: 213.101445377
Chemical FormulaC11H11N5
InChI KeyInChIKey=QPFYXYFORQJZEC-FOCLMDBBSA-N
InChI
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+
IUPAC Name
3-[(E)-2-phenyldiazen-1-yl]pyridine-2,6-diamine
SMILES
NC1=NC(N)=C(C=C1)\N=N\C1=CC=CC=C1
Mass Specshow(10.2 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPyridines and Derivatives
SubclassAminopyridines and Derivatives
Direct parentAminopyridines and Derivatives
Alternative parentsPrimary Aromatic Amines; Benzene and Substituted Derivatives; Azo Compounds; Polyamines
Substituentsbenzene; primary aromatic amine; azo compound; polyamine; amine; primary amine; organonitrogen compound
Classification descriptionThis compound belongs to the aminopyridines and derivatives. These are organic heterocyclic compounds containing an amino group attached to a pyridine ring.
Pharmacology
IndicationFor the symptomatic relief of pain, burning, urgency, frequency, and other discomforts arising from irritation of the lower urinary tract mucosa caused by infection, trauma, surgery, endoscopic procedures, or the passage of sounds or catheters.
PharmacodynamicsPhenazopyridine 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.
Mechanism of actionPhenazopyridine'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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Likely hepatic but also in other tissues. One of the metabolites is acetaminophen.

SubstrateEnzymesProduct
Phenazopyridine
    acetaminophenDetails
    Route of elimination40% hepatic
    Half life7.35 hours
    ClearanceNot Available
    ToxicityMethemoglobinemia generally follows a massive, acute overdose.
    Affected organisms
    • Humans and other mammals
    PathwaysNot Available
    SNP Mediated EffectsNot Available
    SNP Mediated Adverse Drug ReactionsNot Available
    ADMET
    Predicted ADMET features
    Property Value Probability
    Human Intestinal Absorption + 0.9816
    Blood Brain Barrier + 0.874
    Caco-2 permeable + 0.7633
    P-glycoprotein substrate Non-substrate 0.6748
    P-glycoprotein inhibitor I Non-inhibitor 0.9121
    P-glycoprotein inhibitor II Non-inhibitor 0.956
    Renal organic cation transporter Non-inhibitor 0.7745
    CYP450 2C9 substrate Non-substrate 0.8791
    CYP450 2D6 substrate Non-substrate 0.8856
    CYP450 3A4 substrate Non-substrate 0.7528
    CYP450 1A2 substrate Inhibitor 0.9107
    CYP450 2C9 substrate Non-inhibitor 0.7498
    CYP450 2D6 substrate Non-inhibitor 0.9231
    CYP450 2C19 substrate Inhibitor 0.8985
    CYP450 3A4 substrate Non-inhibitor 0.6767
    CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5068
    Ames test AMES toxic 0.9107
    Carcinogenicity Non-carcinogens 0.6868
    Biodegradation Not ready biodegradable 0.9948
    Rat acute toxicity 2.6160 LD50, mol/kg Not applicable
    hERG inhibition (predictor I) Weak inhibitor 0.9554
    hERG inhibition (predictor II) Non-inhibitor 0.8735
    Pharmacoeconomics
    ManufacturersNot Available
    Packagers
    Dosage forms
    FormRouteStrength
    TabletOral
    TabletOral
    Prices
    Unit descriptionCostUnit
    Phenazopyridine hcl 100% powdr3.59USDg
    Pyridium 200 mg tablet1.84USDtablet
    Phenazopyridine 200 mg tablet1.83USDtablet
    Phenazopyridine 100 mg tablet1.82USDtablet
    Phenazopyridine Plus 150-15-0.3 mg tablet1.3USDtablet
    Phenazopyridine plus tablet1.25USDtablet
    Pyridium 100 mg tablet1.09USDtablet
    Phenazopyridine HCl 200 mg tablet0.97USDtablet
    Phenazopyridine HCl 100 mg tablet0.5USDtablet
    Uristat 95 mg tablet0.39USDtablet
    Azo standard 97.5 mg tablet0.36USDtablet
    Urogesic-blue tablet0.36USDtablet
    Azo standard 95 mg tablet0.33USDtablet
    Azo-gesic 95 mg tablet0.22USDtablet
    CVS Pharmacy urinary pain rlf 95 mg tablet0.22USDtablet
    Woman's wellbeing uti rlf tablet0.21USDtablet
    Prodium 95 mg tablet0.19USDtablet
    DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
    PatentsNot Available
    Properties
    Statesolid
    Experimental Properties
    PropertyValueSource
    melting point139 °CPhysProp
    Predicted Properties
    PropertyValueSource
    water solubility2.02e-01 g/lALOGPS
    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 area89.65ChemAxon
    rotatable bond count2ChemAxon
    refractivity68.25ChemAxon
    polarizability22.66ChemAxon
    number of rings2ChemAxon
    bioavailability1ChemAxon
    rule of fiveYesChemAxon
    Ghose filterYesChemAxon
    Veber's ruleNoChemAxon
    MDDR-like ruleNoChemAxon
    Spectra
    SpectraNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    External Links
    ResourceLink
    KEGG CompoundC07429
    PubChem Compound4756
    PubChem Substance46507962
    ChemSpider4592
    PharmGKBPA164746899
    Drug Product Database271489
    RxListhttp://www.rxlist.com/cgi/generic/phenazopyridine.htm
    Drugs.comhttp://www.drugs.com/cdi/phenazopyridine.html
    PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/pyr1365.shtml
    WikipediaPhenazopyridine
    ATC CodesG04BX06
    AHFS Codes
    • 84:08.00
    PDB EntriesNot Available
    FDA labelNot Available
    MSDSshow(73.7 KB)
    Interactions
    Drug InteractionsSearched, but no interactions found.
    Food InteractionsNot Available

    1. Sodium channel protein type 1 subunit alpha

    Kind: protein

    Organism: Human

    Pharmacological action: yes

    Actions: inhibitor

    Components

    Name UniProt ID Details
    Sodium channel protein type 1 subunit alpha P35498 Details

    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
    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. Pubmed

    Comments
    Drug created on July 30, 2007 10:08 / Updated on September 16, 2013 17:14