Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H11N5.ClH |
| Molecular Weight | 249.699 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.NC1=NC(N)=C(C=C1)\N=N\C2=CC=CC=C2
InChI
InChIKey=QQBPIHBUCMDKFG-GEEYTBSJSA-N
InChI=1S/C11H11N5.ClH/c12-10-7-6-9(11(13)14-10)16-15-8-4-2-1-3-5-8;/h1-7H,(H4,12,13,14);1H/b16-15+;
| 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 |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=47185181-607e-4bbe-8850-726af1973cf1Curator'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
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 Although in the early 1930s the medical and scientific communities rescinded the claim that phenazopyridine is bactericidal, a specific mechanism of action has not been identified subsequently.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 |
|---|---|---|---|---|
| Primary | SULFAMETHOXAZOLE AND TRIMETHOPRIM AND PENAZOPYRIDINE HYDROCHLORIDE Approved UsePhenazopyridine 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 Date2001 |
|||
| Primary | PHENAZOPYRIDINE Approved UsePhenazopyridine 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 |
|
| Drug discovery for Duchenne muscular dystrophy via utrophin promoter activation screening. | 2011 |
|
| Effects of phenazopyridine on rat bladder primary afferent activity, and comparison with lidocaine and acetaminophen. | 2010-11 |
|
| Medications and glucose-6-phosphate dehydrogenase deficiency: an evidence-based review. | 2010-09-01 |
|
| Managing the adverse effects of radiation therapy. | 2010-08-15 |
|
| Presumptive hepatotoxicity and rhabdomyolysis secondary to phenazopyridine toxicity in a dog. | 2010-06 |
|
| CdS-sensitized TiO2 in phenazopyridine photo-degradation: catalyst efficiency, stability and feasibility assessment. | 2010-01-15 |
|
| New and emerging agents in the management of lipodystrophy in HIV-infected patients. | 2010 |
|
| Metabotropic glutamate receptors: their therapeutic potential in anxiety. | 2010 |
|
| Ureteral stent discomfort: Etiology and management. | 2009-12-04 |
|
| Miniaturization of powder dissolution measurement and estimation of particle size. | 2009-11 |
|
| Highly regio- and stereoselective synthesis of (Z)-trisubstituted alkenes via propyne bromoboration and tandem Pd-catalyzed cross-coupling. | 2009-09-17 |
|
| Phenazopyridine induces and synchronizes neuronal differentiation of embryonic stem cells. | 2009-09 |
|
| Confirmation of ureteric patency during cystoscopy using phenazopyridine HCl: a low-cost approach. | 2009-09 |
|
| 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 |
|
| Acrocyanosis from phenazopyridine-induced sulfhemoglobinemia mistaken for Raynaud phenomenon. | 2009-04 |
|
| Drug-induced hematologic syndromes. | 2009 |
|
| Determination of phenazopyridine in human plasma by GC-MS and its pharmacokinetics. | 2008-09 |
|
| Elderly woman with orange urine and purple hands. | 2008-07 |
|
| Neurogenic bladder and chronic urinary retention associated with MDMA abuse. | 2008-06 |
|
| Urinary tract infections in pregnancy. | 2008-06 |
|
| A prospective, randomized, double-blinded placebo-controlled comparison of extended release oxybutynin versus phenazopyridine for the management of postoperative ureteral stent discomfort. | 2008-05 |
|
| Two cases of methemoglobinemia following zopiclone ingestion. | 2008-02 |
|
| Patient perceived outcomes of treatments used for interstitial cystitis. | 2008-01 |
|
| Detection of intracellular bacterial communities in human urinary tract infection. | 2007-12 |
|
| [Spectroscopic studies on the binding of phenazopyridine hydrochloride and bovine serum albumin]. | 2007-09 |
|
| Phenazopyridine hydrochloride. | 2004 |
|
| Chronic severe hemolytic anemia from phenazopyridine. | 1995-01-15 |
|
| Chronic severe hemolytic anemia related to surreptitious phenazopyridine abuse. | 1994-08-15 |
|
| [Sedural toxicity]. | 1991-03-15 |
|
| Methemoglobinemia and hemolytic anemia after phenazopyridine hydrochloride (Pyridium) administration in end-stage renal disease. | 1989-03 |
|
| Heinz-body hemolytic anemia associated with phenazopyridine and sulfonamide. | 1989-02 |
|
| Phenazopyridine-induced hemolytic anemia in G-6-PD deficiency. | 1987-11 |
|
| Phenazopyridine and aseptic meningitis. | 1987-01 |
|
| Transient renal failure following phenazopyridine overdose. | 1984-08 |
|
| Phenazopyridine-induced hemolytic anemia. | 1983-06 |
|
| Phenazopyridine-induced hemolytic anemia in a patient with G6PD deficiency. | 1983 |
|
| [Detection and diagnosis of drug induced lithiasis]. | 1983 |
|
| Acute hemolytic anaemia due to phenazopyridine hydrochloride in G-6-PD deficient subject. | 1982-09-04 |
|
| Acquired methemoglobinemia and hemolytic anemia after usual doses of phenazopyridine. | 1982-02 |
|
| Additive nephrotoxicity from roentgenographic contrast media. Its occurrence in phenazopyridine-induced acute renal failure. | 1981-05 |
|
| Phenylazopyridine (Pyridium) and acute renal failure. | 1979-03 |
|
| Inadequacy of information on side effects. | 1978-10-07 |
|
| Rapid increase in calculous size: a possible hazard of phenazopyridine hydrochloride therapy in the presence of already formed stones. | 1978-02 |
|
| Phenazopyridine-induced hepatitis. | 1976-10-09 |
|
| Skin pigmentation and acute renal failure in a patient receiving phenazophyridine therapy. | 1974-05-20 |
|
| Urinary phenazopyridine stones. A complication of therapy. | 1972-09-25 |
|
| Hypersensitivity hepatitis due to phenazopyridine hydrochloride. | 1972-05-18 |
|
| Acute renal failure and pigmentation due to phenazopyridine (Pyridium). | 1970-01 |
|
| Phenazopyridine-hydrochloride haemolysis. | 1969-01-18 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=47185181-607e-4bbe-8850-726af1973cf1
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
| Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 18:12:52 GMT 2025
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| Record UNII |
0EWG668W17
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| Record Status |
Validated (UNII)
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C45178
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SUB03736MIG
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C44434
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203197
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1879
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m8594
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100000085680
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136-40-3
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