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
Synonyms
  • 3-(Phenylazo)-2,6-pyridinediamine
  • Fenazopiridina
Product Ingredients
IngredientUNIICASInChI Key
Phenazopyridine hydrochloride0EWG668W17136-40-3QQBPIHBUCMDKFG-GEEYTBSJSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
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 Tab 100mgTablet100 mgOralDuchesnay Inc.1978-12-311997-08-11Canada
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
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AzoTablet97.5 mg/1Orali-Health, Inc.2012-05-18Not applicableUs
AzoTablet95 mg/1Orali-Health, Inc.2012-05-24Not applicableUs
AzoTablet97.5 mg/1Orali-Health, Inc.2014-03-04Not applicableUs
AZO Urinary Pain ReliefTablet95 mg/1Orali-Health, Inc.2014-11-01Not applicableUs
AZO Urinary Pain ReliefTablet95 mg/1OralA-S Medication Solutions2014-11-01Not applicableUs
AZO Urinary Pain ReliefTablet95 mg/1OralA-S Medication Solutions2014-11-01Not applicableUs
AZO Urinary Pain Relief Maximum StrengthTablet97.5 mg/1Orali-Health, Inc.2015-02-09Not applicableUs
AZO Urinary Pain Relief Maximum StrengthTablet99.5 mg/1Orali-Health, Inc.2018-07-02Not applicableUs
CVS Health Maximum Strength Urinary Pain ReliefTablet97.5 mg/1OralReese Pharmaceutical Company2015-01-15Not applicableUs
CVS Health Urinary Pain ReliefTablet95 mg/1OralReese Pharmaceutical Company2013-07-01Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
UrobioticPhenazopyridine hydrochloride (50 mg/1) + Oxytetracycline hydrochloride (250 mg/1) + Sulfamethizole (250 mg/1)CapsuleOralRoerig2005-12-14Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Azo GesicPhenazopyridine hydrochloride (95 mg/1)TabletOralMajor2011-06-25Not applicableUs
AZO Urinary Tract HealthPhenazopyridine hydrochloride (95 mg/1)TabletOrali-Health, Inc.2014-02-28Not applicableUs
PhenazopyridinePhenazopyridine (200 mg/1)TabletOralBreckenridge Pharmaceutical, Inc.2005-09-012012-03-31Us
PhenazopyridinePhenazopyridine hydrochloride (200 mg/1)TabletOralDirectrx2016-04-14Not applicableUs
PhenazopyridinePhenazopyridine (200 mg/1)TabletOralBlenheim Pharmacal. Inc.2010-10-222012-03-31Us
PhenazopyridinePhenazopyridine hydrochloride (100 mg/1)TabletOralPhysicians Total Care, Inc.1995-01-032013-01-15Us
PhenazopyridinePhenazopyridine (100 mg/1)TabletOralBreckenridge Pharmaceutical, Inc.2005-09-012012-03-31Us
PhenazopyridinePhenazopyridine hydrochloride (100 mg/1mg)TabletOralSola Pharmaceuticals2018-02-192018-03-15Us
PhenazopyridinePhenazopyridine hydrochloride (200 mg/1)TabletOralPhysicians Total Care, Inc.1995-08-112013-01-15Us
PhenazopyridinePhenazopyridine hydrochloride (200 mg/1mg)TabletOralSola Pharmaceuticals2018-02-192018-03-15Us
International/Other Brands
AZO-Standard / Baridium / Phenazodine / Prodium / Pyrazodine / Pyridiate / Pyridium / Sedural / Uristat / Urodine / Urogesic / Viridium
Categories
UNII
K2J09EMJ52
CAS number
94-78-0
Weight
Average: 213.2385
Monoisotopic: 213.101445377
Chemical Formula
C11H11N5
InChI Key
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

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.

Associated Conditions
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.

TargetActionsOrganism
ASodium channel protein type 1 subunit alpha
inhibitor
Human
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcetaminophenThe risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Phenazopyridine.
Amyl NitriteThe risk or severity of methemoglobinemia can be increased when Phenazopyridine is combined with Amyl Nitrite.
AntipyrineThe risk or severity of methemoglobinemia can be increased when Antipyrine is combined with Phenazopyridine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Benzocaine is combined with Phenazopyridine.
ButalbitalThe risk or severity of methemoglobinemia can be increased when Butalbital is combined with Phenazopyridine.
CelecoxibThe risk or severity of methemoglobinemia can be increased when Celecoxib is combined with Phenazopyridine.
ChloroquineThe risk or severity of methemoglobinemia can be increased when Chloroquine is combined with Phenazopyridine.
CyclophosphamideThe risk or severity of methemoglobinemia can be increased when Cyclophosphamide is combined with Phenazopyridine.
DapsoneThe risk or severity of methemoglobinemia can be increased when Dapsone is combined with Phenazopyridine.
FlutamideThe risk or severity of methemoglobinemia can be increased when Flutamide is combined with Phenazopyridine.
Food Interactions
  • Take with food to reduce irritation.

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0015506
KEGG Compound
C07429
PubChem Compound
4756
PubChem Substance
46507962
ChemSpider
4592
BindingDB
50420356
ChEMBL
CHEMBL1242
PharmGKB
PA164746899
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Phenazopyridine
ATC Codes
G04BX06 — Phenazopyridine
AHFS Codes
  • 84:08.00 — Antipruritics and Local Anesthetics
MSDS
Download (73.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingDiagnosticUreteral Injury1
2Active Not RecruitingTreatmentAD / Aging / Alzheimer's Disease (AD) / MCI / Mild Cognitive Impairment (MCI)1
3CompletedTreatmentDysfunctional Voiding / Postoperative pain1
3CompletedTreatmentPain NOS / Urinary Tract Infections (UTIs)1
3Not Yet RecruitingTreatmentDysuria1
3RecruitingTreatmentPostoperative Urinary Retention1
3Unknown StatusTreatmentDysuria1
4CompletedDiagnosticUreteral Patency1
4CompletedTreatmentCatheter-related Bladder Discomfort1
4RecruitingPreventionUrinary Retention1
Not AvailableCompletedDiagnosticCystoscopy1
Not AvailableCompletedScreeningInjury of Ureter1
Not AvailableNot Yet RecruitingDiagnosticUreteral Injury1
Not AvailableRecruitingDiagnosticCystoscopy / Phenazopyridine1
Not AvailableUnknown StatusBasic ScienceHuman Volunteers1
Not AvailableWithdrawnDiagnosticIntraoperative Cystoscopy1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amerifit Inc.
  • Amerisource Health Services Corp.
  • Amkas Laboratories Inc.
  • Amneal Pharmaceuticals
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Belgomex Sprl
  • Boca Pharmacal
  • Breckenridge Pharmaceuticals
  • Bryant Ranch Prepack
  • Comprehensive Consultant Services Inc.
  • Consumers Choice
  • Contract Pharm
  • Corepharma LLC
  • CVS Pharmacy
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Edwards Pharmaceuticals
  • Group Health Cooperative
  • H.J. Harkins Co. Inc.
  • Johnson & Johnson Healthcare
  • Kaiser Foundation Hospital
  • Lehigh Valley Technologies Inc.
  • Liberty Pharmaceuticals
  • Lil' Drug Store
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • Patient First Corp.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmedix
  • Pharmelle LLC
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescript Pharmaceuticals
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Rekah Pharmaceutical Industry Ltd.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Scruggs Pharmacal Co. Inc.
  • Southwood Pharmaceuticals
  • Spectrum Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Sunrise Pharmaceutical Inc.
  • Superior Pharmeceuticals
  • Tya Pharmaceuticals
  • Warner Chilcott Co. Inc.
  • WC Pharmaceuticals
Dosage forms
FormRouteStrength
TabletOral95 mg/1
TabletOral100 mg/1
TabletOral100 mg/1mg
TabletOral200 mg/1mg
TabletOral200 mg/1
Tablet, film coatedOral97.5 mg/1
Tablet, coatedOral100 mg/1
Tablet, coatedOral200 mg/1
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral200 mg/1
Tablet, coatedOral
TabletOral
TabletOral100 mg
TabletOral200 mg
TabletOral97.5 mg/1
Tablet, film coatedOral99.5 mg/1
TabletOral99.5 mg/1
CapsuleOral
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)139 °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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Download (10.2 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-3790000000-b512b9204606a7555a5b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-2970000000-0b1e342d0932d1b1e514
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-05fr-4900000000-ca0b4addc8cef352136e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-053r-9600000000-3269efb012d6f568ca89
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-003r-9100000000-82c1432637ce4b1cf4f4
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-05vk-3920000000-53a0d95ed732abd389e7

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Aminopyridines and derivatives
Direct Parent
Aminopyridines and derivatives
Alternative Parents
Dihydropyridines / Imidolactams / Benzene and substituted derivatives / Heteroaromatic compounds / Azo compounds / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Hydrocarbon derivatives
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
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

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...
Gene Name
SCN1A
Uniprot ID
P35498
Uniprot Name
Sodium channel protein type 1 subunit alpha
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]

Drug created on July 30, 2007 10:08 / Updated on October 21, 2018 20:32