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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
Synonyms
3-(Phenylazo)-2,6-pyridinediamine
Fenazopiridina
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Azo Gesictablet95 mg/1oralMajor Pharmaceuticals2011-06-252016-04-05Us
Azo Urinary Tract Healthtablet95 mg/1oralI Health, Inc.2014-02-282016-04-05Us
Phenazo 100mgtablet100 mgoralValeant Canada Lp Valeant Canada S.E.C.1973-12-31Not applicableCanada
Phenazo 200mgtablet200 mgoralValeant Canada Lp Valeant Canada S.E.C.1979-12-31Not applicableCanada
Phenazopyridine HCltablet100 mg/1oralBoca Pharmacal, Inc2010-09-102015-12-29Us
Phenazopyridine HCltablet200 mg/1oralBoca Pharmacal, Inc2010-09-102015-12-29Us
Phenazopyridine HCltablet200 mg/1oralH.J. Harkins Company, Inc.2010-09-102016-04-05Us
Phenazopyridine HCltablet200 mg/1oralPreferred Pharmaceuticals, Inc2010-09-102016-04-05Us
Phenazopyridine HCltablet100 mg/1oralPreferred Pharmaceuticals, Inc2010-09-102016-04-05Us
Phenazopyridine HCltablet100 mg/1oralbryant ranch prepack2010-09-102016-04-05Us
Phenazopyridine HCltablet200 mg/1oralBlenheim Pharmacal, Inc.2012-06-062016-04-05Us
Phenazopyridine HCltablet100 mg/1oralA S Medication Solutions Llc2010-09-102016-04-05Us
Phenazopyridine HCltablet100 mg/1oralBlenheim Pharmacal, Inc.2011-09-142016-04-05Us
Phenazopyridine HCltablet200 mg/1oralA S Medication Solutions Llc2010-09-102016-04-05Us
Phenazopyridine HCl 100mgtablet100 mg/1oralMethod Pharmaceuticals, Llc2014-12-312016-04-05Us
Phenazopyridine HCl 200mgtablet200 mg/1oralMethod Pharmaceuticals, Llc2014-12-312016-04-05Us
Phenazopyridine Hydrochloridetablet, coated200 mg/1oralNationwide Laboratories, LLC2011-08-022016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralRebel Distributors Corp2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralLiberty Pharmaceuticals, Inc.2011-02-012016-04-23Us
Phenazopyridine Hydrochloridetablet200 mg/1oralMed Vantx, Inc.2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralProficient Rx LP2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralDIRECT RX2014-01-012016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralREMEDYREPACK INC.2015-08-252016-02-22Us
Phenazopyridine Hydrochloridetablet100 mg/1oralECI Pharmaceuticals, LLC2011-08-232016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralREMEDYREPACK INC.2015-08-252016-02-22Us
Phenazopyridine Hydrochloridetablet200 mg/1oralPreferred Pharmaceuticals, Inc.2013-12-032016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralAmneal Pharmaceuticals2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet, coated200 mg/1oralDIRECT RX2015-12-092016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralNorthwind Pharmaceuticals, LLC2014-07-242016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralUnit Dose Services2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet, coated100 mg/1oralNationwide Laboratories, LLC2011-08-022016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralRebel Distributors Corp2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralPreferred Pharmaceuticals, Inc.2013-12-032016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralAmneal Pharmaceuticals2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralREMEDYREPACK INC.2015-09-172016-02-19Us
Phenazopyridine Hydrochloridetablet200 mg/1oralNorthwind Pharmaceuticals2014-06-012016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralClinical Solutions Wholesale2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralA S Medication Solutions Llc2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralAv Kare, Inc.2015-10-072016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralApotheca Inc.2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralReady Meds2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralREMEDYREPACK INC.2015-07-152016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralECI Pharmaceuticals, LLC2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralClinical Solutions Wholesale2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralA S Medication Solutions Llc2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralAv Kare, Inc.2015-10-072016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralBlenheim Pharmacal, Inc.2010-05-122016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralAvera Mc Kennan Hospital2015-09-142016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralREMEDYREPACK INC.2015-03-062016-02-22Us
Phenazopyridine Hydrochloridetablet100 mg/1oralECI Pharmaceuticals, LLC2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralCardinal Health2008-05-092016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralA S Medication Solutions Llc2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralAcella Pharmaceuticals, LLC2011-08-182016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralBlenheim Pharmacal, Inc.2010-05-202016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralREMEDYREPACK INC.2015-01-262016-02-22Us
Phenazopyridine Hydrochloridetablet200 mg/1oralECI Pharmaceuticals, LLC2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralA S Medication Solutions Llc2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralLake Erie Medical DBA Quality Care Products LLC2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralAcella Pharmaceuticals, LLC2011-08-182016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralCarilion Materials Management2011-08-232016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralbryant ranch prepack2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralBurel Pharmaceuticals, Inc2016-02-222016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralECI Pharmaceuticals, LLC2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralLake Erie Medical DBA Quality Care Products LLC2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralAidarex Pharmaceuticals LLC2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralAmerican Health Packaging2013-06-242016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralProficient Rx LP2011-08-182016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralBurel Pharmaceuticals, Inc2016-02-222016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralAidarex Pharmaceuticals LLC2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet100 mg/1oralAmerican Health Packaging2013-06-242016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralProficient Rx LP2011-02-012016-04-05Us
Phenazopyridine Hydrochloridetablet200 mg/1oralECI Pharmaceuticals, LLC2011-08-232016-04-05Us
Pyridiumtablet, film coated200 mg/1oralGemini Laboratories, LLC2011-02-012016-04-05Us
Pyridiumtablet, film coated100 mg/1oralGemini Laboratories, LLC2011-02-012016-04-05Us
Pyridiumtablet, film coated200 mg/1oralGemini Laboratories, LLC2011-02-012016-04-05Us
Pyridiumtablet, film coated100 mg/1oralGemini Laboratories, LLC2011-02-012016-04-05Us
Pyridium 100mgtablet100 mgoralErfa Canada 2012 Inc1981-12-31Not applicableCanada
Pyridium 200mgtablet200 mgoralErfa Canada 2012 Inc1981-12-31Not applicableCanada
Pyronium 0.1gmtablet100 mgoralPro Doc Limitee1960-12-312003-07-31Canada
Pyronium Tab 200mgtablet200 mgoralPro Doc Limitee1976-12-312003-07-31Canada
Vito Reins Tab 100mgtablet100 mgoralDuchesnay Inc1977-12-311999-07-23Canada
Generic Prescription ProductsNot Available
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Azotablet97.5 mg/1oralI Health, Inc.2012-05-182016-04-05Us
Azotablet97.5 mg/1oralI Health, Inc.2014-03-042016-04-05Us
Azotablet95 mg/1oralI Health, Inc.2012-05-242016-04-05Us
Azo Urinary Pain Relieftablet95 mg/1oralI Health, Inc.2014-11-012016-04-05Us
Azo Urinary Pain Relief Maximum Strengthtablet97.5 mg/1oralI Health, Inc.2015-02-092016-04-05Us
Good Neighbor Pharmacy Urinary Pain Relieftablet95 mg/1oralAmerisource Bergen Drug Corp2013-07-012016-04-01Us
Leader Azo Tabs Urinary Tract Analgesictablet95 mg/1oralCardinal Health2004-11-052016-04-05Us
Leader Maximum Strenght Urinary Pain Relieftablet97.5 mg/1oralCardinal Health2009-04-302016-04-05Us
Leader Maximum Strength Urinary Pain Relieftablet97.5 mg/1oralCardinal Health2015-01-152016-04-05Us
Leader Urinary Pain Relieftablet95 mg/1oralCardinal Health2013-07-012016-04-05Us
Meijer Maximum Strength Urinary Pain Relieftablet97.5 mg/1oralMeijer Distribution Inc.2015-01-152016-04-05Us
Phenazotablet95 mg/1oralContract Pharmacal Corp2011-10-252016-04-05Us
Phenazopyridine Hydrochloride 95mgtablet95 mg/1oralAmol Pharmaceuticals Private Limited2015-03-202016-04-05Us
Phenazopyridine Hydrochloride 97.5mgtablet97.5 mg/1oralAmol Pharmaceuticals Private Limited2015-03-162016-04-05Us
Preferred Maximum Strength Urinary Pain Relieftablet97.5 mg/1oralReese Pharmaceutical Co2015-01-152016-04-05Us
Preferred Plus Maximum Strength Urinary Pain Relieftablet97.5 mg/1oralKinray2010-01-042016-04-05Us
Preferred Plus Urinary Pain Relieftablet95 mg/1oralKinray2001-04-232016-04-05Us
Quality Choice Maximum Strength Urinary Pain Relieftablet97.5 mg/1oralChain Drug Marketing Association2010-01-042016-04-05Us
Select Brand Maximum Strength Urinary Pain Relieftablet97.5 mg/1oralSelect Brand Distributors2014-09-262016-04-05Us
Skopko Urinary Pain Relieftablet95 mg/1oralSkopko2013-07-012016-04-05Us
Sunmark Urinary Pain Relieftablet95 mg/1oralMcKesson2013-07-012016-04-05Us
Sunmark Urinary Pain Relief Maximum Strengthtablet97.5 mg/1oralMc Kesson2011-09-102016-04-05Us
Topcare Maximum Strength Urinary Pain Relieftablet97.5 mg/1oralTopco Associates LLC2011-02-012016-04-05Us
Uricalm Maximum Strengthtablet, film coated99.5 mg/1oralAlva Amco Pharmacal Companies, Inc.2008-04-292016-04-05Us
Urinary Pain Relieftablet95 mg/1oralThe Kroger Co2012-05-112016-04-05Us
Urinary Pain Relieftablet95 mg/1oralMcKesson (Sunmark)2010-07-092016-04-05Us
Uristat Uti Relief Paktablet95 mg/1oralInsight Pharmaceuticals LLC2015-04-292016-04-05Us
Uti-paintablet95 mg/1oralMethod Pharmaceuticals2014-11-102016-04-05Us
Walgreens Urinary Pain Relieftablet95 mg/1oralWALGREENS Co2001-04-232016-04-23Us
Walgreens Urinary Pain Relief Maximum Strengthtablet97.5 mg/1oralWalgreens Co.2010-04-052016-04-23Us
Winco Maximum Strength Urinary Pain Relieftablet97.5 mg/1oralWin Co Foods, Llc2015-01-152016-04-05Us
International Brands
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
Salts
Name/CASStructureProperties
Phenazopyridine hydrochloride
ThumbNot applicableDBSALT000915
Categories
UNIIK2J09EMJ52
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
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
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.
Related Articles
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
PropertyValueProbability
Human Intestinal Absorption+0.9816
Blood Brain Barrier+0.874
Caco-2 permeable+0.7633
P-glycoprotein substrateNon-substrate0.6748
P-glycoprotein inhibitor INon-inhibitor0.9121
P-glycoprotein inhibitor IINon-inhibitor0.956
Renal organic cation transporterNon-inhibitor0.7745
CYP450 2C9 substrateNon-substrate0.8791
CYP450 2D6 substrateNon-substrate0.8856
CYP450 3A4 substrateNon-substrate0.7528
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.7498
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.8985
CYP450 3A4 inhibitorNon-inhibitor0.6767
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5068
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.6868
BiodegradationNot ready biodegradable0.9948
Rat acute toxicity2.6160 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9554
hERG inhibition (predictor II)Non-inhibitor0.8735
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral100 mg
Tabletoral200 mg
Tabletoral200 mg/1
Tabletoral100 mg/1
Tablet, coatedoral100 mg/1
Tablet, coatedoral200 mg/1
Tablet, film coatedoral100 mg/1
Tablet, film coatedoral200 mg/1
Tablet, film coatedoral99.5 mg/1
Tabletoral95 mg/1
Tabletoral97.5 mg/1
Prices
Unit descriptionCostUnit
Phenazopyridine hcl 100% powdr3.59USD g
Pyridium 200 mg tablet1.84USD tablet
Phenazopyridine 200 mg tablet1.83USD tablet
Phenazopyridine 100 mg tablet1.82USD tablet
Phenazopyridine Plus 150-15-0.3 mg tablet1.3USD tablet
Phenazopyridine plus tablet1.25USD tablet
Pyridium 100 mg tablet1.09USD tablet
Phenazopyridine HCl 200 mg tablet0.97USD tablet
Phenazopyridine HCl 100 mg tablet0.5USD tablet
Uristat 95 mg tablet0.39USD tablet
Azo standard 97.5 mg tablet0.36USD tablet
Urogesic-blue tablet0.36USD tablet
Azo standard 95 mg tablet0.33USD tablet
Azo-gesic 95 mg tablet0.22USD tablet
CVS Pharmacy urinary pain rlf 95 mg tablet0.22USD tablet
Woman's wellbeing uti rlf tablet0.21USD tablet
Prodium 95 mg tablet0.19USD tablet
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 Solubility0.202 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
Mass Spec (NIST)Download (10.2 KB)
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesG04BX06
AHFS Codes
  • 84:08.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.7 KB)
Interactions
Drug Interactions
Drug
DapsoneThe risk or severity of adverse effects can be increased when Dapsone is combined with Phenazopyridine.
Nitric OxideThe risk or severity of adverse effects can be increased when Nitric Oxide is combined with Phenazopyridine.
PrilocaineThe risk or severity of adverse effects can be increased when Phenazopyridine is combined with Prilocaine.
Sodium NitriteThe risk or severity of adverse effects can be increased when Phenazopyridine is combined with Sodium Nitrite.
Food Interactions
  • Take with food to reduce irritation.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Voltage-gated sodium 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:
228969.49 Da
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 ]
Comments
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Drug created on July 30, 2007 10:08 / Updated on September 16, 2013 17:14