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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
SynonymLanguageCode
3-(Phenylazo)-2,6-pyridinediamineNot AvailableNot Available
FenazopiridinaNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
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
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
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.
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 substrateNon-inhibitor0.7498
CYP450 2D6 substrateNon-inhibitor0.9231
CYP450 2C19 substrateInhibitor0.8985
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
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 ReferenceNot Available
External Links
ATC CodesG04BX06
AHFS Codes
  • 84:08.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.7 KB)
Interactions
Drug Interactions
Drug
Nitric OxideMay enhance the adverse/toxic effect of Methemoglobinemia Associated Agents. Combinations of these agents may increase the likelihood of significant methemoglobinemia.
PrilocaineMethemoglobinemia Associated Agents may enhance the adverse/toxic effect of Prilocaine. Combinations of these agents may increase the likelihood of significant methemoglobinemia.
Food Interactions
  • Take with food to reduce irritation.

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