PHENAZOPYRIDINE

US Previously Marketed

First marketed in 1928

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H11N5
Molecular Weight	213.2385
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC(N)=C(C=C1)\N=N\C2=CC=CC=C2

InChI

InChIKey=QPFYXYFORQJZEC-FOCLMDBBSA-N

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+

HIDE SMILES / InChI

Molecular Formula	C11H11N5
Molecular Weight	213.2385
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=47185181-607e-4bbe-8850-726af1973cf1
Curator's Comment: Description was created based on several sources, including https://www.suna.org/download/members/unjarticles/2004/04jun/207.pdf http://medind.nic.in/iaa/t12/i2/iaat12i2p437.pdf

Phenazopyridine hydrochloride, an azo dye first synthesized in 1914, became widely prescribed for the treatment of urinary tract infections (UTIs). With the assumption that the drug possessed antiseptic properties, phenazopyridine was recommended for UTIs caused by Staphylococcus, Streptococcus, and Escherichia coli. Although in the early 1930s the medical and scientific communities rescinded the claim that phenazopyridine is bactericidal, a specific mechanism of action has not been identified subsequently. Currently, phenazopyridine is classified as a urinary analgesic that relieves burning, urgency, frequency, and pain associated with UTI, trauma, or surgery.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 207 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21105lbl.pdf	Primary		Approved 8583	SULFAMETHOXAZOLE AND TRIMETHOPRIM AND PENAZOPYRIDINE HYDROCHLORIDE Approved Use Phenazopyridine Hydrochloride is indicated for the symptomatic relief of pain, burning, urgency, frequency, and other discomforts arising from irritation of the lower urinary tract mucosa caused by infection. Launch Date 2001
Urinary tract infections 207 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=47185181-607e-4bbe-8850-726af1973cf1	Primary		Approved 8583	PHENAZOPYRIDINE Approved Use Phenazopyridine HCl is indicated for the symptomatic relief of pain, burning, urgency frequency, and other discomforts arising from irritation of the mucosa of the lower urinary tract caused by infection, trauma, surgery, endoscopic procedures, or the passage of sounds or catheters. The use of phenazopyridine for relief of symptoms should not delay definitive diagnosis and treatment of causative conditions. The drug should be used for symptomatic relief of pain and not as a substitute for specific surgery or antimicrobial therapy. Phenazopyridine is compatible with antimicrobial therapy and can help relieve pain and discomfort during the interval before antimicrobial therapy controls the infection. Treatment of a urinary tract infection with phenazopyridine should not exceed 2 days. There is no evidence that the combined administration of phenazopyridine and an antimicrobial provides greater benefit than administration of the antimicrobial alone after 2 days.

PubMed

Title	Date	PubMed
Re: Effects of phenazopyridine on rat bladder primary afferent activity, and comparison with lidocaine and acetaminophen.	2011-11	21993134
Drug discovery for Duchenne muscular dystrophy via utrophin promoter activation screening.	2011	22028826
Effects of phenazopyridine on rat bladder primary afferent activity, and comparison with lidocaine and acetaminophen.	2010-11	20976818
Medications and glucose-6-phosphate dehydrogenase deficiency: an evidence-based review.	2010-09-01	20701405
Managing the adverse effects of radiation therapy.	2010-08-15	20704169
Presumptive hepatotoxicity and rhabdomyolysis secondary to phenazopyridine toxicity in a dog.	2010-06	20636989
CdS-sensitized TiO2 in phenazopyridine photo-degradation: catalyst efficiency, stability and feasibility assessment.	2010-01-15	19744778
New and emerging agents in the management of lipodystrophy in HIV-infected patients.	2010	22096395
Metabotropic glutamate receptors: their therapeutic potential in anxiety.	2010	21309118
Ureteral stent discomfort: Etiology and management.	2009-12-04	19955667
Miniaturization of powder dissolution measurement and estimation of particle size.	2009-11	19937817
Highly regio- and stereoselective synthesis of (Z)-trisubstituted alkenes via propyne bromoboration and tandem Pd-catalyzed cross-coupling.	2009-09-17	19694459
Phenazopyridine induces and synchronizes neuronal differentiation of embryonic stem cells.	2009-09	20196783
Confirmation of ureteric patency during cystoscopy using phenazopyridine HCl: a low-cost approach.	2009-09	19941709
Isolation and characterization of a potential process related impurity of phenazopyridine HCl by preparative HPLC followed by MS-MS and 2D-NMR spectroscopy.	2009-07-12	19376664
Acrocyanosis from phenazopyridine-induced sulfhemoglobinemia mistaken for Raynaud phenomenon.	2009-04	19300288
Drug-induced hematologic syndromes.	2009	19960059
Determination of phenazopyridine in human plasma by GC-MS and its pharmacokinetics.	2008-09	18796223
Elderly woman with orange urine and purple hands.	2008-07	18613989
Neurogenic bladder and chronic urinary retention associated with MDMA abuse.	2008-06	18570171
Urinary tract infections in pregnancy.	2008-06	18556490
A prospective, randomized, double-blinded placebo-controlled comparison of extended release oxybutynin versus phenazopyridine for the management of postoperative ureteral stent discomfort.	2008-05	18339420
Two cases of methemoglobinemia following zopiclone ingestion.	2008-02	18259966
Patient perceived outcomes of treatments used for interstitial cystitis.	2008-01	18242366
Detection of intracellular bacterial communities in human urinary tract infection.	2007-12	18092884
[Spectroscopic studies on the binding of phenazopyridine hydrochloride and bovine serum albumin].	2007-09	18051539
Phenazopyridine hydrochloride.	2004	21089943
Chronic severe hemolytic anemia from phenazopyridine.	1995-01-15	7992996
Chronic severe hemolytic anemia related to surreptitious phenazopyridine abuse.	1994-08-15	8037417
[Sedural toxicity].	1991-03-15	1879765
Methemoglobinemia and hemolytic anemia after phenazopyridine hydrochloride (Pyridium) administration in end-stage renal disease.	1989-03	2922627
Heinz-body hemolytic anemia associated with phenazopyridine and sulfonamide.	1989-02	2786291
Phenazopyridine-induced hemolytic anemia in G-6-PD deficiency.	1987-11	3678069
Phenazopyridine and aseptic meningitis.	1987-01	3789573
Transient renal failure following phenazopyridine overdose.	1984-08	6464254
Phenazopyridine-induced hemolytic anemia.	1983-06	6868236
Phenazopyridine-induced hemolytic anemia in a patient with G6PD deficiency.	1983	6410650
[Detection and diagnosis of drug induced lithiasis].	1983	6139048
Acute hemolytic anaemia due to phenazopyridine hydrochloride in G-6-PD deficient subject.	1982-09-04	6125724
Acquired methemoglobinemia and hemolytic anemia after usual doses of phenazopyridine.	1982-02	7075467
Additive nephrotoxicity from roentgenographic contrast media. Its occurrence in phenazopyridine-induced acute renal failure.	1981-05	7235788
Phenylazopyridine (Pyridium) and acute renal failure.	1979-03	426430
Inadequacy of information on side effects.	1978-10-07	709187
Rapid increase in calculous size: a possible hazard of phenazopyridine hydrochloride therapy in the presence of already formed stones.	1978-02	633496
Phenazopyridine-induced hepatitis.	1976-10-09	990717
Skin pigmentation and acute renal failure in a patient receiving phenazophyridine therapy.	1974-05-20	4406341
Urinary phenazopyridine stones. A complication of therapy.	1972-09-25	5068650
Hypersensitivity hepatitis due to phenazopyridine hydrochloride.	1972-05-18	5018866
Acute renal failure and pigmentation due to phenazopyridine (Pyridium).	1970-01	5410400
Phenazopyridine-hydrochloride haemolysis.	1969-01-18	4178260

Patents

Sample Use Guides

In Vivo Use Guide

200 mg 3 times daily after meals. When used concomitantly with an antibacterial agent for the treatment of a urinary tract infection, the administration of phenazopyridine should not exceed 2 days. If symptoms persist, the patient should be re-evaluated.

Route of Administration: Oral

In Vitro Use Guide

3 uM phenazopyridine enhances neuronal differentiation of human embryonic stem cells cells and allows the generation of a monolayer of synchronized neural progenitors

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:55:20 GMT 2025` Edited by `admin` on `Mon Mar 31 17:55:20 GMT 2025`
Record UNII	K2J09EMJ52
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FENAZOPIRIDINA

Preferred Name

English

PHENAZOPYRIDINE

Official Name

English

PHENAZOPYRIDINE [VANDF]

Common Name

English

NSC-145895

Code

English

2,6-DIAMINO-3-(PHENYLAZO)PYRIDINE

Systematic Name

English

Phenazopyridine [WHO-DD]

Common Name

English

phenazopyridine [INN]

Common Name

English

PHENAZOPYRIDINE [HSDB]

Common Name

English

2,6-PYRIDINEDIAMINE, 3-(PHENYLAZO)-

Systematic Name

English

PHENAZOPYRIDINE [MI]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QG04BX56