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Details

Stereochemistry ACHIRAL
Molecular Formula C11H11N5
Molecular Weight 213.239
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PHENAZOPYRIDINE

SMILES

c1ccc(cc1)/N=N/c2ccc(=N)[nH]c2N

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

Description
Curator's Comment:: 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 Although in the early 1930s the medical and scientific communities rescinded the claim that phenazopyridine is bactericidal, a specific mechanism of action has not been identified subsequently.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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

993513600000
Primary
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

PubMed

TitleDatePubMed
Hypersensitivity hepatitis due to phenazopyridine hydrochloride.
1972 May 18
Skin pigmentation and acute renal failure in a patient receiving phenazophyridine therapy.
1974 May 20
Phenazopyridine-induced hepatitis.
1976 Oct 9
Rapid increase in calculous size: a possible hazard of phenazopyridine hydrochloride therapy in the presence of already formed stones.
1978 Feb
Transient renal failure following phenazopyridine overdose.
1984 Aug
Phenazopyridine and aseptic meningitis.
1987 Jan
Heinz-body hemolytic anemia associated with phenazopyridine and sulfonamide.
1989 Feb
Chronic severe hemolytic anemia related to surreptitious phenazopyridine abuse.
1994 Aug 15
Methemoglobinemia due to ingestion of at most three pills of pyridium in a 2-year-old: case report and review.
2003 Aug
PAMPA--a drug absorption in vitro model. 5. Unstirred water layer in iso-pH mapping assays and pKa(flux)--optimized design (pOD-PAMPA).
2003 Dec
Selective blockade of mGlu5 metabotropic glutamate receptors is protective against acetaminophen hepatotoxicity in mice.
2003 Feb
Oxidant hemolysis.
2003 Nov 1
Electron transport in bipyridinium films.
2004
Consumer knowledge of over-the-counter phenazopyridine.
2004 May-Jun
Phenazopyridine-induced sulfhemoglobinemia.
2005 Jun
Multiple adverse effects of pyridium: a case report.
2006 Jan
Interstitial cystitis/painful bladder syndrome.
2007 Feb
Vesicovaginal fistula repair without intentional cystotomy using the laparoscopic robotic approach: a case report.
2007 Jul-Sep
Use of phenazopyridine for reducing discomfort during embryo transfer.
2007 May
Development and validation of a gas chromatography-mass spectrometry method for the determination of phenazopyridine in rat plasma: application to the pharmacokinetic study.
2007 Nov
Two cases of methemoglobinemia following zopiclone ingestion.
2008 Feb
Elderly woman with orange urine and purple hands.
2008 Jul
Urinary tract infections in pregnancy.
2008 Jun
A prospective, randomized, double-blinded placebo-controlled comparison of extended release oxybutynin versus phenazopyridine for the management of postoperative ureteral stent discomfort.
2008 May
Drug-induced hematologic syndromes.
2009
Acrocyanosis from phenazopyridine-induced sulfhemoglobinemia mistaken for Raynaud phenomenon.
2009 Apr
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
Miniaturization of powder dissolution measurement and estimation of particle size.
2009 Nov
New and emerging agents in the management of lipodystrophy in HIV-infected patients.
2010
Drug discovery for Duchenne muscular dystrophy via utrophin promoter activation screening.
2011
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: This drug has not been found by FDA to be safe and effective, and this labeling has not been approved by FDA
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
3 uM phenazopyridine enhances neuronal differentiation of human embryonic stem cells cells and allows the generation of a monolayer of synchronized neural progenitors
Name Type Language
PHENAZOPYRIDINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
PHENAZOPYRIDINE [VANDF]
Common Name English
NSC-145895
Code English
PHENAZOPYRIDINE [WHO-DD]
Common Name English
2,6-DIAMINO-3-(PHENYLAZO)PYRIDINE
Systematic 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
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
LIVERTOX 766
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
NCI_THESAURUS C2198
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
WHO-ATC G04BX06
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
WHO-VATC QG04BX06
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
Code System Code Type Description
DRUG CENTRAL
2120
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
PRIMARY
MERCK INDEX
M8594
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
PRIMARY Merck Index
RXCUI
8120
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C29357
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
PRIMARY
ChEMBL
CHEMBL1242
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
PRIMARY
FDA UNII
K2J09EMJ52
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
PRIMARY
ECHA (EC/EINECS)
202-363-2
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
PRIMARY
EVMPD
SUB09754MIG
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
PRIMARY
CAS
94-78-0
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
PRIMARY
WIKIPEDIA
PHENAZOPYRIDINE
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
PRIMARY
EPA CompTox
94-78-0
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
PRIMARY
HSDB
3153
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
PRIMARY
INN
357
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
PRIMARY
DRUG BANK
DB01438
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
PRIMARY
LACTMED
Phenazopyridine
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
PRIMARY
IUPHAR
7616
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
PRIMARY
MESH
D010621
Created by admin on Sat Jun 26 04:49:12 UTC 2021 , Edited by admin on Sat Jun 26 04:49:12 UTC 2021
PRIMARY