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 marketed in the US 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 Although in the early 1930s the medical and scientific communities rescinded the claim that phenazopyridine is bactericidal, a specific mechanism of action has not been identified subsequently.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 205 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21105lbl.pdf	Primary		Approved 8429	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 205 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=47185181-607e-4bbe-8850-726af1973cf1	Primary		Approved 8429	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
Phenazopyridine-hydrochloride haemolysis.	1969 Jan 18	4178260
Acute renal failure and pigmentation due to phenazopyridine (Pyridium).	1970 Jan	5410400
Hypersensitivity hepatitis due to phenazopyridine hydrochloride.	1972 May 18	5018866
Urinary phenazopyridine stones. A complication of therapy.	1972 Sep 25	5068650
Skin pigmentation and acute renal failure in a patient receiving phenazophyridine therapy.	1974 May 20	4406341
Phenazopyridine-induced hepatitis.	1976 Oct 9	990717
Rapid increase in calculous size: a possible hazard of phenazopyridine hydrochloride therapy in the presence of already formed stones.	1978 Feb	633496
Inadequacy of information on side effects.	1978 Oct 7	709187
Phenylazopyridine (Pyridium) and acute renal failure.	1979 Mar	426430
Additive nephrotoxicity from roentgenographic contrast media. Its occurrence in phenazopyridine-induced acute renal failure.	1981 May	7235788
Acquired methemoglobinemia and hemolytic anemia after usual doses of phenazopyridine.	1982 Feb	7075467
Acute hemolytic anaemia due to phenazopyridine hydrochloride in G-6-PD deficient subject.	1982 Sep 4	6125724
Phenazopyridine-induced hemolytic anemia in a patient with G6PD deficiency.	1983	6410650
[Detection and diagnosis of drug induced lithiasis].	1983	6139048
Phenazopyridine-induced hemolytic anemia.	1983 Jun	6868236
Transient renal failure following phenazopyridine overdose.	1984 Aug	6464254
Phenazopyridine and aseptic meningitis.	1987 Jan	3789573
Phenazopyridine-induced hemolytic anemia in G-6-PD deficiency.	1987 Nov	3678069
Heinz-body hemolytic anemia associated with phenazopyridine and sulfonamide.	1989 Feb	2786291
Methemoglobinemia and hemolytic anemia after phenazopyridine hydrochloride (Pyridium) administration in end-stage renal disease.	1989 Mar	2922627
[Sedural toxicity].	1991 Mar 15	1879765
Chronic severe hemolytic anemia related to surreptitious phenazopyridine abuse.	1994 Aug 15	8037417
Chronic severe hemolytic anemia from phenazopyridine.	1995 Jan 15	7992996
Phenazopyridine hydrochloride.	2004	21089943
Detection of intracellular bacterial communities in human urinary tract infection.	2007 Dec	18092884
[Spectroscopic studies on the binding of phenazopyridine hydrochloride and bovine serum albumin].	2007 Sep	18051539
Two cases of methemoglobinemia following zopiclone ingestion.	2008 Feb	18259966
Patient perceived outcomes of treatments used for interstitial cystitis.	2008 Jan	18242366
Elderly woman with orange urine and purple hands.	2008 Jul	18613989
Neurogenic bladder and chronic urinary retention associated with MDMA abuse.	2008 Jun	18570171
Urinary tract infections in pregnancy.	2008 Jun	18556490
A prospective, randomized, double-blinded placebo-controlled comparison of extended release oxybutynin versus phenazopyridine for the management of postoperative ureteral stent discomfort.	2008 May	18339420
Determination of phenazopyridine in human plasma by GC-MS and its pharmacokinetics.	2008 Sep	18796223
Drug-induced hematologic syndromes.	2009	19960059
Acrocyanosis from phenazopyridine-induced sulfhemoglobinemia mistaken for Raynaud phenomenon.	2009 Apr	19300288
Isolation and characterization of a potential process related impurity of phenazopyridine HCl by preparative HPLC followed by MS-MS and 2D-NMR spectroscopy.	2009 Jul 12	19376664
Miniaturization of powder dissolution measurement and estimation of particle size.	2009 Nov	19937817
Ureteral stent discomfort: Etiology and management.	2009 Oct-Dec	19955667
Phenazopyridine induces and synchronizes neuronal differentiation of embryonic stem cells.	2009 Sep	20196783
Confirmation of ureteric patency during cystoscopy using phenazopyridine HCl: a low-cost approach.	2009 Sep	19941709
Highly regio- and stereoselective synthesis of (Z)-trisubstituted alkenes via propyne bromoboration and tandem Pd-catalyzed cross-coupling.	2009 Sep 17	19694459
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
Managing the adverse effects of radiation therapy.	2010 Aug 15	20704169
CdS-sensitized TiO2 in phenazopyridine photo-degradation: catalyst efficiency, stability and feasibility assessment.	2010 Jan 15	19744778
Presumptive hepatotoxicity and rhabdomyolysis secondary to phenazopyridine toxicity in a dog.	2010 Jun	20636989
Effects of phenazopyridine on rat bladder primary afferent activity, and comparison with lidocaine and acetaminophen.	2010 Nov	20976818
Medications and glucose-6-phosphate dehydrogenase deficiency: an evidence-based review.	2010 Sep 1	20701405
Drug discovery for Duchenne muscular dystrophy via utrophin promoter activation screening.	2011	22028826
Re: Effects of phenazopyridine on rat bladder primary afferent activity, and comparison with lidocaine and acetaminophen.	2011 Nov	21993134

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 `Fri Dec 15 15:21:57 GMT 2023` Edited by `admin` on `Fri Dec 15 15:21:57 GMT 2023`
Record UNII	K2J09EMJ52
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

FENAZOPIRIDINA

Brand 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