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

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

MedKoo CAT#: 414064

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

Description: 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

CAS# 94-78-0 (free base)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 414064
Name: Phenazopyridine Free Base
CAS#: 94-78-0 (free base)
Chemical Formula: C11H11N5
Exact Mass: 213.10
Molecular Weight: 213.244
Elemental Analysis: C, 61.96; H, 5.20; N, 32.84

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 324	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

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Product Data:

Product Data

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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.

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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1: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Phenazopyridine. 2018 Oct 31. PMID: 30000565.

2: Rehfuss A, Mahon J, Sorokin I, Smith C, Stein BS. Phenazopyridine: A Preoperative Way to Identify Ureteral Orifices. Urology. 2018 May;115:36-38. doi: 10.1016/j.urology.2018.02.023. Epub 2018 Mar 1. PMID: 29501712.

3: Shore SN, Britnell SR, Brown JN. Safety analysis of long-term phenazopyridine use for radiation cystitis. J Oncol Pharm Pract. 2020 Mar;26(2):306-311. doi: 10.1177/1078155219842646. Epub 2019 Apr 22. PMID: 31006341.

4: Tsukanov AY, Makushin DG, Mirzakadiev AA, Zolotov IA. [Influence of phenazopyridine on the well-being of patients during and after cystoscopy]. Urologiia. 2020 Sep;(4):50-54. Russian. PMID: 32897014.

5: Strom EM, Chaudhry ZQ, Guo R, Maisonet AJ, Holschneider CH, Wieslander CK. Effectiveness of Assessing Ureteral Patency Using Preoperative Phenazopyridine. Female Pelvic Med Reconstr Surg. 2019 Jul/Aug;25(4):289-293. doi: 10.1097/SPV.0000000000000540. PMID: 29300258; PMCID: PMC6034993.

6: Agrawal A, Davis N, Hsieh R, Stallard S. Methemoglobinaemia with chronic phenazopyridine ingestion. BMJ Case Rep. 2019 Feb 15;12(2):e227538. doi: 10.1136/bcr-2018-227538. PMID: 30772834; PMCID: PMC6388894.

7: Murphy T, Fernandez M. Acquired methemoglobinemia from phenazopyridine use. Int J Emerg Med. 2018 Nov 12;11(1):45. doi: 10.1186/s12245-018-0208-5. PMID: 31179913; PMCID: PMC6326144.

8: Dueñas-Garcia OF, Sierra T, Nicasio E, Leung K, Hall CD, Flynn MK. The Effect of Preoperative Phenazopyridine on Urinary Retention Following Midurethral Sling. Female Pelvic Med Reconstr Surg. 2018 Jan/Feb;24(1):43-47. doi: 10.1097/SPV.0000000000000404. PMID: 28230566.

9: Phenazopyridine and phenazopyridine hydrochloride. IARC Monogr Eval Carcinog Risk Chem Hum. 1980;24:163-73. PMID: 7009390.

10: Youngster I, Arcavi L, Schechmaster R, Akayzen Y, Popliski H, Shimonov J, Beig S, Berkovitch M. Medications and glucose-6-phosphate dehydrogenase deficiency: an evidence-based review. Drug Saf. 2010 Sep 1;33(9):713-26. doi: 10.2165/11536520-000000000-00000. PMID: 20701405.

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