Synonym
Phenazopyridine Hydrochloride; Phenazopyridine HCl; Urodine; Pyridium; Phenazodine; Azo Dine; Azo Gesic; Azo Natural; Azo Standard; Azo-Dine; Azo-Gesic;Rugby Brand of Phenazopyridine Hydrochloride; United Research Brand of Phenazopyridine Hydrochloride;
IUPAC/Chemical Name
3-phenyldiazenylpyridine-2,6-diamine;hydrochloride
InChi Key
QQBPIHBUCMDKFG-GEEYTBSJSA-N
InChi Code
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+;
SMILES Code
C1=CC=C(C=C1)N=NC2=C(N=C(C=C2)N)N.Cl
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Phenazopyridine Hydrochloride can be used as an analgesic for the urinary tract.
In vitro activity:
The effects of PAP (phenazopyridine) on the relevant TRP channels (TRPV1, TRPA1, TRPM8, TRPM3) expressed in HEK293 or CHO cells was investigated using Fura-2-based calcium measurements and whole-cell patch-clamp recordings. PAP rapidly and reversibly inhibits responses of TRPM8 expressed in HEK293 cells to cold and menthol, with IC50 values between 2 and 10 μM. It acts by shifting the voltage dependence of channel activation towards positive potentials, opposite to the effect of menthol. PAP also inhibits TRPM8-mediated, menthol-evoked calcium responses in lumbosacral DRG neurons.
Reference: Eur J Pharmacol. 2023 Mar 5;942:175512. https://pubmed.ncbi.nlm.nih.gov/36657655/
In vivo activity:
Importantly, this study demonstrated that phenazopyridine not only promoted RPS23RG1/Rps23rg1 expression, but also reduced AD-like pathologies and cognitive impairments in the APP/PS1 AD model mice. This study also determined a critical negative regulatory domain of RPS23RG1 within nucleotide positions +1177 to +1187 and found that the transcription factor SMAD3 bound to this domain. Inhibition of SMAD3 promoted RPS23RG1 expression. Moreover, phenazopyridine reduced SMAD3 binding to the RPS23RG1 promoter without affecting SMAD3 phosphorylation and nuclear localization.
Reference: Neuropsychopharmacology. 2022 Nov;47(12):2042-2050. https://pubmed.ncbi.nlm.nih.gov/35821069/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
1.0 |
4.00 |
|
| DMSO |
25.3 |
101.45 |
|
| DMSO:PBS (pH 7.2) (1:1) |
0.5 |
2.00 |
|
| Water |
1.0 |
4.00 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
249.70
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Luyts N, Daniluk J, Freitas ACN, Bazeli B, Janssens A, Mulier M, Everaerts W, Voets T. Inhibition of TRPM8 by the urinary tract analgesic drug phenazopyridine. Eur J Pharmacol. 2023 Mar 5;942:175512. doi: 10.1016/j.ejphar.2023.175512. Epub 2023 Jan 16. PMID: 36657655.
2. Preynat-Seauve O, Nguyen EB, Westermaier Y, Héritier M, Tardy S, Cambet Y, Feyeux M, Caillon A, Scapozza L, Krause KH. Novel Mechanism for an Old Drug: Phenazopyridine is a Kinase Inhibitor Affecting Autophagy and Cellular Differentiation. Front Pharmacol. 2021 Aug 4;12:664608. doi: 10.3389/fphar.2021.664608. PMID: 34421588; PMCID: PMC8371461.
3. Wang C, Zhang Y, Zhao D, Huo Y, Xie J, Zhang X, Luo H, Xu H, Zhang YW. Phenazopyridine promotes RPS23RG1/Rps23rg1 transcription and ameliorates Alzheimer-associated phenotypes in mice. Neuropsychopharmacology. 2022 Nov;47(12):2042-2050. doi: 10.1038/s41386-022-01373-7. Epub 2022 Jul 11. PMID: 35821069; PMCID: PMC9556769.
In vitro protocol:
1. Luyts N, Daniluk J, Freitas ACN, Bazeli B, Janssens A, Mulier M, Everaerts W, Voets T. Inhibition of TRPM8 by the urinary tract analgesic drug phenazopyridine. Eur J Pharmacol. 2023 Mar 5;942:175512. doi: 10.1016/j.ejphar.2023.175512. Epub 2023 Jan 16. PMID: 36657655.
2. Preynat-Seauve O, Nguyen EB, Westermaier Y, Héritier M, Tardy S, Cambet Y, Feyeux M, Caillon A, Scapozza L, Krause KH. Novel Mechanism for an Old Drug: Phenazopyridine is a Kinase Inhibitor Affecting Autophagy and Cellular Differentiation. Front Pharmacol. 2021 Aug 4;12:664608. doi: 10.3389/fphar.2021.664608. PMID: 34421588; PMCID: PMC8371461.
In vivo protocol:
1. Wang C, Zhang Y, Zhao D, Huo Y, Xie J, Zhang X, Luo H, Xu H, Zhang YW. Phenazopyridine promotes RPS23RG1/Rps23rg1 transcription and ameliorates Alzheimer-associated phenotypes in mice. Neuropsychopharmacology. 2022 Nov;47(12):2042-2050. doi: 10.1038/s41386-022-01373-7. Epub 2022 Jul 11. PMID: 35821069; PMCID: PMC9556769.
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26838908.
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