Phenazopyridine hydrochloride

• CAS: 136-40-3
• Catalog Number: ACM136403
• Category: Main Products
• Molecular Weight: 249.70
• Molecular Formula: C₁₁H₁₁N₅·HCl
• Synonyms: nc150; pyrizin; 2,6-diamino-3-phenylazopyridine hydrochloride; sedural; Phenazopyridine .HCl; uriplex; 3-phenyldiazenylpyridine-2,6-diamine monohydrochloride; 3-Phenylazo-2,6-diaMinopyridine Monohydrochloride; pirid; azodyne; 3-(Phenyldiazenyl)pyridine-2,6-diamine hydrochloride; dolonil; phenazopyridine HCl; Phenazopyridine hydrochloride; URODINE; 2,6-Pyridinediamine (3-[(1E)-2-phenyldiazenyl]; Phenazopyridine HCl; urazium; Phenazopyridine Hydrochloride; 2,6-DIAMINO-3-(PHENYLAZO)-PYRIDINE HYDROCHLORIDE; 2,6-Diamino-3-(phenylazo)pyridine hydrochloride,Urodine; giracid
• IUPAC Name: 3-phenyldiazenylpyridine-2,6-diamine;hydrochloride
• Canonical SMILES: C1=CC=C(C=C1)N=NC2=C(N=C(C=C2)N)N.Cl
• InChI Key: QQBPIHBUCMDKFG-UHFFFAOYSA-N
• Boiling Point: 442.3ºC at 760 mmHg
• Melting Point: 139ºC
• Flash Point: 221.3ºC
• Appearance: solid
• EC Number: 205-243-8
• Exact Mass: 249.07800
• Hazard Statements: Xn:Harmful
• Safety Description: S26-S36/37
• UN Number: 2811

Case Study

Enzymatic Oligomerization of Phenazopyridine Hydrochloride

Kolcu, Feyza. Journal of Molecular Structure, 2019, 1188, 76-85.

Phenazopyridine hydrochloride (PHP) is used as a preservative and analgesic in medicinal chemistry and is also an azo dye. In order to avoid the health hazards of azo dyes, this work aims to develop environmentally friendly and green synthetic methods to produce aromatic amine oligomers containing azo groups. This study described the enzymatic oligomerization pathway based on PHP.
Enzymatic oligomerization of PHP
· A solution containing PHP (1.2 mmol, 0.3 g) and HRP (6 mg) was prepared by dissolving them in a mixture of 4 mL of 0.1 M phosphate buffer (pH 7) and 12 mL of 1,4-dioxane.
· The enzymatic oligomerization took place in a beaker, where 230 µL of a 35% aqueous H2O2 solution was added dropwise over the course of one hour, followed by the addition of 1 mL of aqueous H2O2 over five hours. The reaction was allowed to proceed at room temperature for four hours.
· The resulting brown O-PHP product was then filtered and thoroughly washed with distilled water (3 x 50 mL) and ethanol (2 x 25 mL) to remove any remaining enzyme, buffer, and unreacted monomer. Finally, the product was dried in a vacuum oven at 50 °C, yielding 59%.

Comparison of the Selective Determination Methods for Phenazopyridine Hydrochloride

Attia, Khalid AM, et al. Analytical Chemistry Letters, 2016, 6(6), 863-873.

Phenazopyridine hydrochloride (PAP) has analgesic effects on the urinary tract mucosa and can relieve the pain symptoms of diseases such as cystitis and urethritis. However, 2,3,6-tribenzopyridine (TAP), a metabolite of PAP, is known to cause muscle necrosis and renal damage in rats. In this work, four different spectrophotometric methods were applied to selectively determine phenazopyridine hydrochloride (PAP) in the presence of oxidative degradation products (TAP) in bulk powders and pharmaceutical preparations.
Comparison of different determination methods
· The four spectrophotometric methods were first derivative (1D), ratio difference spectrophotometry (RDSM), first derivative of ratio spectra (1DD), and dual wavelength (DW).
· In the case of the 1D method, peak amplitudes were recorded at 370 nm, while the differences in peak amplitudes between 428 nm and 276 nm were assessed for RDSM. Conversely, the 1DD method measured peak amplitudes at 360 nm, with the absorbance difference between 425 nm and 256 nm evaluated for DW.
· Regression analysis for the calibration curves of PAP indicated a strong linear relationship across a concentration range of 1-14 μg/ml for all four methods proposed. These methods were effectively utilized for determining the levels of PAP in pharmaceutical formulations.
· Furthermore, the results were compared statistically to a previously reported HPLC method, which revealed no significant differences between the methods under investigation and the reported one regarding validation parameters.

Custom Q&A

What is the molecular formula of Phenazopyridine hydrochloride?

The molecular formula of Phenazopyridine hydrochloride is C11H11N5.ClHC11H12ClN5.

What is the molecular weight of Phenazopyridine hydrochloride?

The molecular weight of Phenazopyridine hydrochloride is 249.70 g/mol.

What are the synonyms of Phenazopyridine hydrochloride?

The synonyms of Phenazopyridine hydrochloride are Phenazopyridine HCl, Pyridium, and Urodine.

What does Phenazopyridine hydrochloride look like?

Phenazopyridine hydrochloride appears as brick-red microcrystals with a slight violet luster or a purple powder.

What is the taste of Phenazopyridine hydrochloride?

Phenazopyridine hydrochloride has a slightly bitter taste.

What is the use of Phenazopyridine hydrochloride?

Phenazopyridine hydrochloride is used orally as a urinary tract analgesic.

What are the potential side effects of Phenazopyridine hydrochloride?

The potential side effects of Phenazopyridine hydrochloride administration can include nausea, interference with the oxygen-carrying capacity of red blood cells (methemoglobinemia), hemolytic anemia, as well as renal and hepatic toxicity.

How soluble is Phenazopyridine hydrochloride?

Phenazopyridine hydrochloride is only slightly soluble in cold water and ethanol but is soluble in boiling water, acetic acid, glycerol, ethylene glycol, and propylene glycol.

Can Phenazopyridine hydrochloride be a carcinogenic agent?

Yes, Phenazopyridine hydrochloride has a role as a carcinogenic agent and is reasonably anticipated to be a human carcinogen.

What is the InChIKey of Phenazopyridine hydrochloride?

The InChIKey of Phenazopyridine hydrochloride is QQBPIHBUCMDKFG-UHFFFAOYSA-N.