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+;
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 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 Although in the early 1930s the medical and scientific communities rescinded the claim that phenazopyridine is bactericidal, a specific mechanism of action has not been identified subsequently.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 |
|---|---|---|---|---|
| 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 |
|---|---|---|
| Hypersensitivity hepatitis due to phenazopyridine hydrochloride. | 1972 May 18 |
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| Urinary phenazopyridine stones. A complication of therapy. | 1972 Sep 25 |
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| Skin pigmentation and acute renal failure in a patient receiving phenazophyridine therapy. | 1974 May 20 |
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| Phenazopyridine-induced hepatitis. | 1976 Oct 9 |
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| Rapid increase in calculous size: a possible hazard of phenazopyridine hydrochloride therapy in the presence of already formed stones. | 1978 Feb |
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| Inadequacy of information on side effects. | 1978 Oct 7 |
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| Phenylazopyridine (Pyridium) and acute renal failure. | 1979 Mar |
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| Additive nephrotoxicity from roentgenographic contrast media. Its occurrence in phenazopyridine-induced acute renal failure. | 1981 May |
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| Acquired methemoglobinemia and hemolytic anemia after usual doses of phenazopyridine. | 1982 Feb |
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| Acute hemolytic anaemia due to phenazopyridine hydrochloride in G-6-PD deficient subject. | 1982 Sep 4 |
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| Phenazopyridine-induced hemolytic anemia in a patient with G6PD deficiency. | 1983 |
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| Phenazopyridine-induced hemolytic anemia. | 1983 Jun |
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| Phenazopyridine and aseptic meningitis. | 1987 Jan |
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| Methemoglobinemia and hemolytic anemia after phenazopyridine hydrochloride (Pyridium) administration in end-stage renal disease. | 1989 Mar |
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| [Sedural toxicity]. | 1991 Mar 15 |
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| Chronic severe hemolytic anemia related to surreptitious phenazopyridine abuse. | 1994 Aug 15 |
|
| Chronic severe hemolytic anemia from phenazopyridine. | 1995 Jan 15 |
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| Phenazopyridine hydrochloride. | 2004 |
|
| Urinary tract infection drug helps pain, hinders cure. | 2004 Aug |
|
| Application of stochastic resonance to quantitative analysis of weak chromatographic signal of phenazopyridine in human plasma. | 2005 Jul |
|
| Phenazopyridine-induced sulfhemoglobinemia. | 2005 Jun |
|
| 1H, 13C and 15N NMR assignments of phenazopyridine derivatives. | 2005 Mar |
|
| Determination of phenazopyridine in human plasma via LC-MS and subsequent development of a pharmacokinetic model. | 2005 May |
|
| Red urine in a returning traveller. | 2005 Nov |
|
| Ciprofloxacin bioavailability is enhanced by oral co-administration with phenazopyridine: a pharmacokinetic study in a Mexican population. | 2006 |
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| A simple pharmacokinetics subroutine for modeling double peak phenomenon. | 2006 Apr |
|
| Multiple adverse effects of pyridium: a case report. | 2006 Jan |
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| Acute renal failure due to phenazopyridine (Pyridium) overdose: case report and review of the literature. | 2006 Nov |
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| An over-the-counter omission. | 2006 Sep |
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| Detection of intracellular bacterial communities in human urinary tract infection. | 2007 Dec |
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| Interstitial cystitis/painful bladder syndrome. | 2007 Feb |
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| 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 |
|
| Elderly woman with orange urine and purple hands. | 2008 Jul |
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| A prospective, randomized, double-blinded placebo-controlled comparison of extended release oxybutynin versus phenazopyridine for the management of postoperative ureteral stent discomfort. | 2008 May |
|
| Determination of phenazopyridine in human plasma by GC-MS and its pharmacokinetics. | 2008 Sep |
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| Drug-induced hematologic syndromes. | 2009 |
|
| 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 |
|
| Ureteral stent discomfort: Etiology and management. | 2009 Oct-Dec |
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| Phenazopyridine induces and synchronizes neuronal differentiation of embryonic stem cells. | 2009 Sep |
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| Confirmation of ureteric patency during cystoscopy using phenazopyridine HCl: a low-cost approach. | 2009 Sep |
|
| Highly regio- and stereoselective synthesis of (Z)-trisubstituted alkenes via propyne bromoboration and tandem Pd-catalyzed cross-coupling. | 2009 Sep 17 |
|
| New and emerging agents in the management of lipodystrophy in HIV-infected patients. | 2010 |
|
| Managing the adverse effects of radiation therapy. | 2010 Aug 15 |
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| CdS-sensitized TiO2 in phenazopyridine photo-degradation: catalyst efficiency, stability and feasibility assessment. | 2010 Jan 15 |
|
| Presumptive hepatotoxicity and rhabdomyolysis secondary to phenazopyridine toxicity in a dog. | 2010 Jun |
|
| Effects of phenazopyridine on rat bladder primary afferent activity, and comparison with lidocaine and acetaminophen. | 2010 Nov |
|
| Medications and glucose-6-phosphate dehydrogenase deficiency: an evidence-based review. | 2010 Sep 1 |
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
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C45178
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C44434
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m8594
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136-40-3
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ACTIVE MOIETY
SUBSTANCE RECORD
