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MedKoo Cat#: 414064 | Name: Phenazopyridine Free Base
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Phenazopyridine Free Base is A local anesthetic that has been used in urinary tract disorders. Its use is limited by problems with toxicity (primarily blood disorders) and potential carcinogenicity.

Chemical Structure

Phenazopyridine Free Base
Phenazopyridine Free Base
CAS#94-78-0 (free base)

Theoretical Analysis

MedKoo Cat#: 414064

Name: Phenazopyridine Free Base

CAS#: 94-78-0 (free base)

Chemical Formula: C11H11N5

Exact Mass: 213.1014

Molecular Weight: 213.24

Elemental Analysis: C, 61.96; H, 5.20; N, 32.84

Price and Availability

Size Price Availability Quantity
5mg USD 324.00 2 Weeks
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Related CAS #
94-78-0 (free base) 136-40-3 (HCl)
Synonym
Phenazopyridine Free Base; HSDB3153; HSDB-3153; HSDB 3153
IUPAC/Chemical Name
2,6-Pyridinediamine, 3-(phenylazo)-
InChi Key
QPFYXYFORQJZEC-FOCLMDBBSA-N
InChi Code
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+
SMILES Code
NC1=NC(N)=CC=C1/N=N/C2=CC=CC=C2
Appearance
Solid powder
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Phenazopyridine Free Base is A local anesthetic that has been used in urinary tract disorders.
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/

Preparing Stock Solutions

The following data is based on the product molecular weight 213.24 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.

Recalculate based on batch purity %
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.
1: eastham JH, Patel P. Phenazopyridine. 2024 Aug 18. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2024 Jan–. PMID: 35593852. 2: Moritz BW, Chouairi F, Tosh A, Toffaletti JG, Rackley CR. A 36-Year-Old Woman With Intermittent Cyanosis. Chest. 2024 Aug;166(2):e29-e33. doi: 10.1016/j.chest.2024.03.017. PMID: 39122304. 3: Bruckmann FDS, Foucaud Y, Pinheiro RF, Silva LFO, Oliveira MLS, Badawi M, Dotto GL. Removal of phenazopyridine from water, synthetic urine, and real sample by adsorption using graphene oxide: A DFT theoretical/experimental approach. Chemosphere. 2024 Sep;363:142738. doi: 10.1016/j.chemosphere.2024.142738. Epub 2024 Jul 14. PMID: 39004147. 4: da Silva Bruckmann F, Fuhr ACFP, Pinheiro RF, Knani S, Alruwaili A, Pinto D, Silva LFO, Dotto GL. Statistical physical modeling insights for urinary analgesic drug adsorption on carbon nanomaterial derivative. Environ Sci Pollut Res Int. 2024 Jul;31(31):44374-44384. doi: 10.1007/s11356-024-34115-x. Epub 2024 Jun 29. PMID: 38949732. 5: Kapur A, Jericevic D, Wang R, Stewart L, Siddique M. Cost Analysis of Oral Phenazopyridine vs Intravesical Lidocaine for Preprocedural Analgesia for Intradetrusor OnabotulinumtoxinA Injections. Urol Pract. 2024 Sep;11(5):800-805. doi: 10.1097/UPJ.0000000000000628. Epub 2024 Jun 21. PMID: 38913587. 6: Pursnani S, Streeper NM. Case of drug-induced kidney stone from overuse of phenazopyridine. Can J Urol. 2024 Jun;31(3):11911-11913. PMID: 38912947. 7: Dufresne K, DiMaggio DA Jr, Maduta CS, Brinsmade SR, McCormick JK. Discovery of an antivirulence compound that targets the Staphylococcus aureus SaeRS two- component system to inhibit toxic shock syndrome toxin-1 production. J Biol Chem. 2024 Jul;300(7):107455. doi: 10.1016/j.jbc.2024.107455. Epub 2024 Jun 7. PMID: 38852884; PMCID: PMC11328871. 8: Gronich N, Rosh B, Stein N, Saliba W. Medications and Acute Hemolysis in G6PD-Deficient Patients - A Real-World Study. Clin Pharmacol Ther. 2024 Jun 6. doi: 10.1002/cpt.3333. Epub ahead of print. PMID: 38842030. 9: Long AR, Mortara EL, Mendoza BN, Fink EC, Sacco FX, Ciesla MJ, Stack TMM. Sequence similarity network analysis of drug- and dye-modifying azoreductase enzymes found in the human gut microbiome. Arch Biochem Biophys. 2024 Jul;757:110025. doi: 10.1016/j.abb.2024.110025. Epub 2024 May 11. PMID: 38740275; PMCID: PMC11295148. 10: Bharuka V, Meshram R, Munjewar PK. Comprehensive Review of Urinary Tract Infections in Renal Transplant Recipients: Clinical Insights and Management Strategies. Cureus. 2024 Feb 8;16(2):e53882. doi: 10.7759/cureus.53882. PMID: 38465031; PMCID: PMC10924982. 11: Joseph J, Sundararaj JJ, Shekinah S, Kamalakannan S. Rare cause of dyspnoea: phenazopyridine-induced methemoglobinemia. BMJ Support Palliat Care. 2024 Jan 2:spcare-2023-004692. doi: 10.1136/spcare-2023-004692. Epub ahead of print. PMID: 38167589. 12: Thompson JC, Halder GE, Jeppson PC, Alas A, Balgobin S, Dieter AA, Houlihan S, Miranne J, Sleemi A, Balk EM, Mama S, Meriwether KV, Antosh DD. Repair of Vesicovaginal Fistulae: A Systematic Review. Obstet Gynecol. 2024 Feb 1;143(2):229-241. doi: 10.1097/AOG.0000000000005468. Epub 2023 Nov 30. PMID: 38033311. 13: Neto FS, Hachul H, Pereira MA, Filho CI. Efficacy of methenamine with methylthioninium in the treatment of dysuria: a randomized clinical study. Int Urogynecol J. 2023 Dec;34(12):3051-3058. doi: 10.1007/s00192-023-05669-0. Epub 2023 Oct 18. PMID: 37851092; PMCID: PMC10756887. 14: Sharma V, Robertson K, Domagalski J. A Case That Will Take Your Breath Away: Acquired Methemoglobinemia Related to Trimethoprim-Sulfamethoxazole and Phenazopyridine Ingestion for Treatment of Urinary Tract Infection. WMJ. 2023 Sep;122(4):287-289. PMID: 37768772. 15: Sharifi Teshnizi M, Karimi M. TiO2/graphene composite nanofibers for efficient photocatalytic degradation of pharmaceutical compounds: Rifampin, Phenazopyridine, Azathioprine. Environ Sci Pollut Res Int. 2023 Oct;30(49):107956-107969. doi: 10.1007/s11356-023-29869-9. Epub 2023 Sep 25. PMID: 37747607. 16: Soderstrom M, Foster DV, Hamidi ZS, Anderson JT. Sulfhemoglobinemia in a 53-Year-Old With a History of Phenazopyridine Misuse. Cureus. 2023 Jun 25;15(6):e40944. doi: 10.7759/cureus.40944. PMID: 37496545; PMCID: PMC10368485. 17: Josephy PD, Allen-Vercoe E. Reductive metabolism of azo dyes and drugs: Toxicological implications. Food Chem Toxicol. 2023 Aug;178:113932. doi: 10.1016/j.fct.2023.113932. Epub 2023 Jul 12. PMID: 37451600. 18: Menakuru SR, Dhillon VS, Atta M, Mann K, Salih A. Phenazopyridine-Induced Methemoglobinemia in a Jehovah's Witness Treated with High-Dose Ascorbic Acid Due to Methylene Blue Contradictions: A Case Report and Review of the Literature. Hematol Rep. 2023 May 24;15(2):325-330. doi: 10.3390/hematolrep15020034. PMID: 37367083; PMCID: PMC10298695. 19: Huang A, Li L, Liu X, Lian Q, Guo G, Xu T, Lu X, Ma L, Ma H, Yu Y, Yao L. Hedgehog signaling is a potential therapeutic target for vascular calcification. Gene. 2023 Jul 1;872:147457. doi: 10.1016/j.gene.2023.147457. Epub 2023 May 2. PMID: 37141952. 20: Yamamoto H, Shanker R, Sugano K. Application of Population Balance Model to Simulate Precipitation of Weak Base and Zwitterionic Drugs in Gastrointestinal pH Environment. Mol Pharm. 2023 Apr 3;20(4):2266-2275. doi: 10.1021/acs.molpharmaceut.3c00088. Epub 2023 Mar 17. PMID: 36929729.