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Identification
Name Phenazopyridine
Accession Number DB01438
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • PAP
  • PDP
  • Pyridacil
Brand names
  • Azo-Standard
  • Baridium
  • Phenazodine
  • Phenylazo
  • Prodium
  • Pyrazodine
  • Pyridiate
  • Pyridium
  • Sedural
  • Suladyne
  • Uristat
  • Urodine
  • Urogesic
  • Viridium
Brand name mixtures Not Available
Categories
  • Anesthetics, Local
CAS number 94-78-0
Weight Average: 213.2385
Monoisotopic: 213.101445377
Chemical Formula C11H11N5
InChI Key InChIKey=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+
Plain Text
IUPAC Name
3-[(E)-2-phenyldiazen-1-yl]pyridine-2,6-diamine
SMILES
NC1=CC=C(\N=N\C2=CC=CC=C2)C(N)=N1
Plain Text
Mass Spec show (10.2 KB)
Taxonomy
Kingdom Organic
Classes
  • Pyridines and Derivatives
  • Benzene and Derivatives
  • Aminopyridines and Derivatives
  • Anilines
Substructures
  • Pyridines and Derivatives
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Aminopyridines and Derivatives
  • Azo compounds
  • Heterocyclic compounds
  • Aromatic compounds
  • Anilines
Pharmacology
Indication For 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.
Pharmacodynamics Phenazopyridine 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 action 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.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism

Likely hepatic but also in other tissues. One of the metabolites is acetaminophen.
Route of elimination 40% hepatic
Half life 7.35 hours
Clearance Not Available
Toxicity Methemoglobinemia generally follows a massive, acute overdose.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Tablet Oral
Prices
Unit description Cost Unit
Phenazopyridine hcl 100% powdr 3.59 USD g
Pyridium 200 mg tablet 1.84 USD tablet
Phenazopyridine 200 mg tablet 1.83 USD tablet
Phenazopyridine 100 mg tablet 1.82 USD tablet
Phenazopyridine Plus 150-15-0.3 mg tablet 1.3 USD tablet
Phenazopyridine plus tablet 1.25 USD tablet
Pyridium 100 mg tablet 1.09 USD tablet
Phenazopyridine HCl 200 mg tablet 0.97 USD tablet
Phenazopyridine HCl 100 mg tablet 0.5 USD tablet
Uristat 95 mg tablet 0.39 USD tablet
Azo standard 97.5 mg tablet 0.36 USD tablet
Urogesic-blue tablet 0.36 USD tablet
Azo standard 95 mg tablet 0.33 USD tablet
Azo-gesic 95 mg tablet 0.22 USD tablet
CVS Pharmacy urinary pain rlf 95 mg tablet 0.22 USD tablet
Woman's wellbeing uti rlf tablet 0.21 USD tablet
Prodium 95 mg tablet 0.19 USD tablet
Patents Not Available
Properties
State solid
Melting point 139 oC
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 2.02e-01 g/l ALOGPS
logP 2.31 ALOGPS
logP 2.69 ChemAxon Molconvert
logS -3.02 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 5 ChemAxon Molconvert
hydrogen donor count 2 ChemAxon Molconvert
polar surface area 89.65 ChemAxon Molconvert
rotatable bond count 2 ChemAxon Molconvert
refractivity 68.25 ChemAxon Molconvert
polarizability 22.66 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07429 Link_out
PubChem Compound 4756 Link_out
PubChem Substance 46507962 Link_out
ChemSpider 4592 Link_out
PharmGKB PA450898 Link_out
Drug Product Database 271489 Link_out
RxList http://www.rxlist.com/cgi/generic/phenazopyridine.htm Link_out
Drugs.com http://www.drugs.com/cdi/phenazopyridine.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/pyr1365.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Phenazopyridine Link_out
ATC Codes
  • G04BX06
AHFS Codes
  • 84:08.00
PDB Entries Not Available
FDA label Not Available
MSDS show (73.7 KB)
Interactions
Drug Interactions
Drug Interaction
Food Interactions
  • Take with food to reduce irritation.
Targets

1. Sodium channel protein type 1 subunit alpha

Pharmacological action: yes
Actions: inhibitor

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

Organism class: human
UniProt ID: P35498 Link_out
Gene: SCN1A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 August 07, 2011 00:06

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.