Identification

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Name
Phenazopyridine
Accession Number
DB01438
Type
Small Molecule
Groups
Approved
Description

Phenazopyridine, also known as Pyridium, is a urinary tract analgesic used for the short-term management of urinary tract irritation and its associated unpleasant symptoms such as burning and pain during urination. In the USA, this drug was previously marked by Roche but has been discontinued by the FDA.16 It is still used in various parts of the world. Ingestion of phenazopyridine is found to change the appearance of the urine by imparting an orange or red color, as it is considered an azo dye.15

Structure
Thumb
Synonyms
  • 2,6-Diamino-3-(phenylazo)pyridine
  • 2,6-Diamino-3-phenylazopyridine
  • 3-(Phenylazo)-2,6-pyridinediamine
  • Fenazopiridina
  • Phenazopyridine
  • Phénazopyridine
  • Phenazopyridinum
Product Ingredients
IngredientUNIICASInChI Key
Phenazopyridine hydrochloride0EWG668W17136-40-3QQBPIHBUCMDKFG-GEEYTBSJSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Azo GesicTablet95 mg/1OralMajor2011-06-252018-07-06Us
AZO Urinary Tract HealthTablet95 mg/1Orali-Health, Inc.2014-02-28Not applicableUs
Phenazo 100mgTabletOralValeant Canada Lp Valeant Canada S.E.C.1973-12-31Not applicableCanada
Phenazo 200mgTabletOralValeant Canada Lp Valeant Canada S.E.C.1979-12-31Not applicableCanada
PhenazopyridineTablet200 mg/1OralPhysicians Total Care, Inc.1995-08-112013-01-15Us
PhenazopyridineTablet100 mg/1mgOralSola Pharmaceuticals2018-02-192018-03-15Us
PhenazopyridineTablet200 mg/1OralBlenheim Pharmacal. Inc.2010-10-222012-03-31Us
PhenazopyridineTablet100 mg/1OralPhysicians Total Care, Inc.1995-01-032013-01-15Us
PhenazopyridineTablet200 mg/1OralBreckenridge Pharmaceutical, Inc.2005-09-012012-03-31Us
PhenazopyridineTablet200 mg/1mgOralSola Pharmaceuticals2018-02-192018-03-15Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AzoTablet97.5 mg/1Orali-Health, Inc.2014-03-04Not applicableUs
AzoTablet97.5 mg/1Orali-Health, Inc.2012-05-18Not applicableUs
AzoTablet95 mg/1Orali-Health, Inc.2012-05-24Not 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 StrengthTablet99.5 mg/1Orali-Health, Inc.2018-07-02Not applicableUs
AZO Urinary Pain Relief Maximum StrengthTablet97.5 mg/1Orali-Health, Inc.2015-02-09Not applicableUs
Care One Maximum Strength Urinary Pain ReliefTablet97.5 mg/1OralAmerican Sales2010-01-04Not applicableUs
Care One Maximum Strength Urinary Pain ReliefTablet99.5 mg/1OralRetail Business Services , LLC.2019-09-20Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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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
AzoPhenazopyridine hydrochloride (97.5 mg/1)TabletOrali-Health, Inc.2014-03-04Not applicableUs
AzoPhenazopyridine hydrochloride (97.5 mg/1)TabletOrali-Health, Inc.2012-05-18Not applicableUs
AzoPhenazopyridine hydrochloride (95 mg/1)TabletOrali-Health, Inc.2012-05-24Not applicableUs
Azo GesicPhenazopyridine hydrochloride (95 mg/1)TabletOralMajor2011-06-252018-07-06Us
AZO Urinary Pain ReliefPhenazopyridine hydrochloride (95 mg/1)TabletOralA-S Medication Solutions2014-11-01Not applicableUs
AZO Urinary Pain ReliefPhenazopyridine hydrochloride (95 mg/1)TabletOrali-Health, Inc.2014-11-01Not applicableUs
AZO Urinary Pain ReliefPhenazopyridine hydrochloride (95 mg/1)TabletOralA-S Medication Solutions2014-11-01Not applicableUs
AZO Urinary Pain Relief Maximum StrengthPhenazopyridine hydrochloride (99.5 mg/1)TabletOrali-Health, Inc.2018-07-02Not applicableUs
AZO Urinary Pain Relief Maximum StrengthPhenazopyridine hydrochloride (97.5 mg/1)TabletOrali-Health, Inc.2015-02-09Not applicableUs
AZO Urinary Tract HealthPhenazopyridine hydrochloride (95 mg/1)TabletOrali-Health, Inc.2014-02-28Not applicableUs
International/Other Brands
AZO-Standard / Baridium / Phenazodine / Prodium / Pyrazodine / Pyridiate / 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

Phenazopyridine hydrochloride is indicated to relieve uncomfortable symptoms that occur as a consequence of mucosal irritation of the lower urinary tract in adults. The irritation may be a result of trauma, surgery, endoscopic procedures, infection, or the insertion of instruments or urinary catheters.14 Phenazopyridine may be used in combination with antimicrobial therapy but is not used as an antimicrobial agent. It contributes to the relief of discomfort and pain before antimicrobial therapy begins to take effect. It is important to note that the duration of treatment with this drug should last a maximum of 2 days.14 Phenazopyridine is available in many countries as an over the counter drug.7

Associated Conditions
Pharmacodynamics

Phenazopyridine acts as a local anesthetic offering relief from irritating conditions of the urinary tract. It relieves urinary urgency frequency, burning, pain, and discomfort.14,18

A note on urine and skin discoloration and interference with test results

Yellowing of the skin or sclerae of the eyes may indicate that the accumulation of phenazopyridine has occurred. This may be a consequence of overdose, decreased renal function, taking the drug for over two days. Elderly patients may be at particular risk due to a decline in renal function, potentiating the risk of phenazopyridine accumulation. The drug should be discontinued if yellowing of the skin or sclerae is observed.14 Hemolytic anemia is a risk of phenazopyridine, especially in cases of overdose. In addition to the above effects, this drug may impart an orange or red color of urine and feces, causing staining of clothing. Other body fluids may also be stained, and in patients wearing contact lenses, phenazopyridine may cause lens staining. Due to its orange-red color, this drug may interfere with laboratory requiring colorimetric, spectrophotometric or fluorometric methods of analysis.14 In patients with G6PD enzyme deficiency, this drug poses a greater risk of hemolysis, even at normal doses and is not recommended.14

A note on carcinogenesis

Based on the results of in vivo studies in rats, this drug has been listed as a carcinogen in the USA since 1981. Rats given this drug were found to demonstrate increased rates of hepatocellular carcinoma and colorectal tumors.23 Use this agent with caution and limit the administration of this drug when possible.

Mechanism of action

The full mechanism of action of phenazopyridine is not fully elucidated18, however, it is reported to exert a direct topical analgesic effect on the mucosal lining of the urinary tract via the inhibition of voltage-gated sodium channels17 and possibly group A nerve fibers, as suggested by the results of a study in rats.8 The above actions likely lead to the relief of unpleasant urinary symptoms.15

TargetActionsOrganism
ASodium channel protein type 1 subunit alpha
inhibitor
Humans
UGroup A nerve fibers
inhibitor
Rat
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Phenazopyridine is absorbed in the gastrointestinal tract.10,20 The mean Cmax is 65.00 ± 29.23 ng/mL, the mean Tmax is 2.48 ± 0.50 h, and the mean AUC(0 – ∞)is 431.77 ± 87.82 ng.h/mL.11

Volume of distribution

Small, trace quantities of phenazopyridine are thought to cross the placenta and the blood-brain barrier, reaching cerebrospinal fluid.15 A pharmacokinetic study in rats determined that phenazopyridine metabolites were present in high levels in the kidney and liver.12

Protein binding
Not Available
Metabolism

Phenazopyridine is metabolized in the liver, and acetaminophen has been discovered to be one metabolite of this drug.15 Hydroxylation is a pathway by which this drug is metabolized.13 In humans, 5-hydroxyl PAP is the major metabolite (48.3% of the dose) and small amounts of other hydroxy metabolites are produced.11,22 The metabolism of phenazopyridine produces aniline, which is likely associated with methemoglobinemia in some patients or in the case of an overdose. This dye accumulates in the skin, and yellow skin pigmentation has been observed when high doses of this drug have been taken.14 Triaminopyridine is also a metabolite of phenazopyridine.22 During a pharmacokinetic study, aniline contributed to approximately 6.9% of urinary metabolites. N acetyl-p-aminophenol (acetaminophen) contributes to about 18%, P-aminophenol (PAP) contributes 24%, and finally, DPP (unchanged phenazopyridine) contributes to about 41% of excreted urinary metabolites.10

Route of elimination

Up to 65% of an oral phenazopyridine dose is quickly excreted by the kidneys as unchanged drug measured in the urine.15 The pharmacokinetics of this drug have not been evaluated in depth in man. In a small group of healthy research volunteers, 90% of a daily 600 mg oral dose of phenazopyridine hydrochloride was found to be excreted within 1 day, with 41% as unchanged drug and 49% as phenazopyridine metabolites.14 Another study in humans determined that 80.07 ± 4.54 percent of the dose was cleared in the urine within 48 hours of administration.9 In rats, biliary excretion was high, with 40.7% of a dose excreted in 8 hours.12

Half life

The mean elimination half-life of phenazopyridine is 7.35 hours in rats with healthy renal function.12 The half-life in man is not readily vailable in the literature.

Clearance

This drug is rapidly excreted by the kidneys, up to 65% of a dose administered orally may be excreted as unchanged drug in the urine. The clearance of phenazopyridine may be decreased with impaired renal or hepatic function and is contraindicated in these conditions.14

Toxicity

The oral LD50 of phenazopyridine in rats is 472 mg/kg.19

Overdose information

Administering excess phenazopyridine above the daily recommended dose in those with healthy or impaired kidney function may increase the drug concentration and predispose the patient to toxicity. When a large overdose occurs, methemoglobinemia results.5,6 To treat this condition, Methylene blue at 1 to 2 mg/kg/dose should be administered intravenously as a 1% solution as deemed necessary. Its administration is likely to cause a rapid reduction of the methemoglobinemia state and relieve the associated cyanosis. Hemolytic anemia is also a risk when an overdose occurs, and “bite cells” may be observed in a blood smear after an overdose with phenazopyridine. Red blood cell G6PD deficiency may increase the risk of hemolysis, and even normal doses can lead to methemoglobinemia in patients with this condition. Nephrotoxicity, renal failure, and hepatic impairment may also occur in a case of overdose with this drug. Administer symptomatic and supportive treatment as necessary.4,7,18

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirPhenazopyridine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarbosePhenazopyridine may decrease the excretion rate of Acarbose which could result in a higher serum level.
AceclofenacThe risk or severity of nephrotoxicity can be increased when Phenazopyridine is combined with Aceclofenac.
AcemetacinThe risk or severity of nephrotoxicity can be increased when Phenazopyridine is combined with Acemetacin.
AcetaminophenThe risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Phenazopyridine.
AcetazolamideAcetazolamide may increase the excretion rate of Phenazopyridine which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidThe risk or severity of nephrotoxicity can be increased when Acetylsalicylic acid is combined with Phenazopyridine.
AclidiniumPhenazopyridine may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastinePhenazopyridine may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirThe risk or severity of nephrotoxicity can be increased when Acyclovir is combined with Phenazopyridine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take with food to reduce irritation.

References

General References
  1. Shore SN, Britnell SR, Brown JN: Safety analysis of long-term phenazopyridine use for radiation cystitis. J Oncol Pharm Pract. 2019 Apr 22:1078155219842646. doi: 10.1177/1078155219842646. [PubMed:31006341]
  2. Suter DM, Preynat-Seauve O, Tirefort D, Feki A, Krause KH: Phenazopyridine induces and synchronizes neuronal differentiation of embryonic stem cells. J Cell Mol Med. 2009 Sep;13(9B):3517-27. doi: 10.1111/j.1582-4934.2009.00660.x. [PubMed:20196783]
  3. Rehfuss A, Mahon J, Sorokin I, Smith C, Stein BS: Phenazopyridine: A Preoperative Way to Identify Ureteral Orifices. Urology. 2018 May;115:36-38. doi: 10.1016/j.urology.2018.02.023. Epub 2018 Mar 1. [PubMed:29501712]
  4. Onder AM, Espinoza V, Berho ME, Chandar J, Zilleruelo G, Abitbol C: Acute renal failure due to phenazopyridine (Pyridium) overdose: case report and review of the literature. Pediatr Nephrol. 2006 Nov;21(11):1760-4. doi: 10.1007/s00467-006-0196-1. Epub 2006 Aug 1. [PubMed:16897003]
  5. Gold NA, Bithoney WG: Methemoglobinemia due to ingestion of at most three pills of pyridium in a 2-year-old: case report and review. J Emerg Med. 2003 Aug;25(2):143-8. [PubMed:12901999]
  6. Murphy T, Fernandez M: Acquired methemoglobinemia from phenazopyridine use. Int J Emerg Med. 2018 Nov 12;11(1):45. doi: 10.1186/s12245-018-0208-5. [PubMed:31179913]
  7. Chang LC, Kuo CW, Chau T, Lin SH: Phenazopyridine-induced hemolytic anemia in advanced kidney disease. J Am Geriatr Soc. 2014 Dec;62(12):2464-6. doi: 10.1111/jgs.13161. [PubMed:25516057]
  8. 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]
  9. Thomas BH, Whitehouse LW, Solomonraj G, Paul CJ: Excretion of phenazopyridine and its metabolites in the urine of humans, rats, mice, and guinea pigs. J Pharm Sci. 1990 Apr;79(4):321-5. doi: 10.1002/jps.2600790410. [PubMed:2352143]
  10. Johnson WJ, Chartrand A: The metabolism and excretion of phenazopyridine hydrochloride in animals and man. Toxicol Appl Pharmacol. 1976 Aug;37(2):371-6. doi: 10.1016/0041-008x(76)90100-9. [PubMed:982458]
  11. Li KJ, Chen QH, Zhang Z, Zhou P, Li P, Liu J, Zhu J: Determination of phenazopyridine in human plasma by GC-MS and its pharmacokinetics. J Chromatogr Sci. 2008 Sep;46(8):686-9. doi: 10.1093/chromsci/46.8.686. [PubMed:18796223]
  12. Thomas BH, Whitehouse LW, Solomonraj G, Paul CJ: Metabolism and disposition of phenazopyridine in rat. Xenobiotica. 1993 Feb;23(2):99-105. [PubMed:8498084]
  13. Pitre D, Maffei-Facino R: Isolation and identification of two hydroxylated metabolites of phenazopyridine in rat urine. Farmaco Sci. 1977 Jun;32(6):453-60. [PubMed:872925]
  14. Phenazopyridine Hydrochloride [Link]
  15. Drug summary: phenazopyridine [Link]
  16. FDA information Phenazopyridine [Link]
  17. HMDB, phenazopyridine [Link]
  18. Phenazopyridine DailyMed [Link]
  19. MSDS, Phenazopyridine [Link]
  20. UPMC: Final Diagnosis -- Suicide Attempt with Ingestion of Pyridium Tablets [Link]
  21. Intracellular Drug Bioavailability: Effect of Neutral Lipids and Phospholipids [Link]
  22. O Factors Affecting Drug Metabolism [Link]
  23. Phenazopyridine hydrochloride [Link]
External Links
Human Metabolome Database
HMDB0015506
KEGG Drug
D08346
KEGG Compound
C07429
PubChem Compound
4756
PubChem Substance
46507962
ChemSpider
4592
BindingDB
50420356
ChEBI
71416
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
2SuspendedTreatmentAD / Aging / Alzheimer's Disease (AD) / MCI / Mild Cognitive Impairment (MCI)1
3CompletedTreatmentDysfunctional Voiding / Postoperative pain1
3CompletedTreatmentPain / Urinary Tract Infection1
3CompletedTreatmentPostoperative Urinary Retention1
3CompletedTreatmentUncomplicated Urinary Tract Infections1
3Not Yet RecruitingTreatmentDysuria1
3Unknown StatusTreatmentDysuria1
4CompletedDiagnosticUreteral Patency1
4CompletedPreventionUrinary Retention1
4CompletedTreatmentCatheter-related Bladder Discomfort1
Not AvailableActive Not RecruitingDiagnosticCystoscopy / Phenazopyridine1
Not AvailableCompletedDiagnosticCystoscopy1
Not AvailableCompletedScreeningInjury of Ureter1
Not AvailableNot Yet RecruitingDiagnosticUreteral Injury1
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 coatedOral95 mg/1
Tablet, coatedOral
TabletOral
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral200 mg/1
TabletOral
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)139https://www.lookchem.com/Phenazopyridine-hydrochloride/
boiling point (°C)442.3 ºC https://www.lookchem.com/Phenazopyridine-hydrochloride/
logP2.62https://pdfs.semanticscholar.org/182c/23f8f9a5935f172b01241dd7c06d8d72b6f3.pdf
logS3.83https://www.sciencedirect.com/topics/pharmacology-toxicology-and-pharmaceutical-science/phenazopyridine
pKa5.05https://pdfs.semanticscholar.org/182c/23f8f9a5935f172b01241dd7c06d8d72b6f3.pdf
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
Humans
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
This is a potential target.
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. Compound report card [Link]
  2. HMDB, phenazopyridine [Link]
2. Group A nerve fibers
Kind
Group
Organism
Rat
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
This target information was obtained from one study in rat tissue.
References
  1. 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 November 12, 2019 22:45