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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 KeyQPFYXYFORQJZEC-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
Not Available
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

Targets

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

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