Pirenoxine sodium salt | CAS# 51410-30-1 (salt) | anti-cataract

MedKoo Cat#: 412439 | Name: Pirenoxine sodium salt

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Description:

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

Pirenoxine sodium salt is an anti-cataract agent which is used in many asian countries under the name Catalin. Although its efficacy is not proved scientifically, the drug may play an important role in cataract prevention. It is supposed that the anti-cataract effect of pirenoxine results from inhibition of sulfhydryl combination of quinoid substances with lens proteins and the inhibition leads to the maintenance of lens transparency.

Chemical Structure

Pirenoxine sodium salt

CAS#51410-30-1 (salt)

Theoretical Analysis

MedKoo Cat#: 412439

Name: Pirenoxine sodium salt

CAS#: 51410-30-1 (salt)

Chemical Formula: C16H7N2NaO5

Exact Mass: 0.0000

Molecular Weight: 330.23

Elemental Analysis: C, 58.19; H, 2.14; N, 8.48; Na, 6.96; O, 24.22

Price and Availability

Size	Price	Availability
1mg	USD 400.00	2 Weeks
2mg	USD 600.00	2 Weeks
10mg	USD 1,000.00	2 Weeks

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Related CAS #

1043-21-6 (free base) 51410-30-1 (salt)

Synonym

Pirenoxine sodium salt; EINECS 257-181-6

IUPAC/Chemical Name

5H-Pyrido(3,2-a)phenoxazine-3-carboxylic acid, 1-hydroxy-5-oxo-, monosodium salt

InChi Key

HDQXPMXHXZNPKE-UHFFFAOYSA-M

InChi Code

InChI=1S/C16H8N2O5.Na/c19-9-5-8(16(21)22)18-14-10(20)6-12-15(13(9)14)17-7-3-1-2-4-11(7)23-12;/h1-6H,(H,18,19)(H,21,22);/q;+1/p-1

SMILES Code

O=C(C1=CC(O)=C2C(C(C=C3OC4=C(N=C32)C=CC=C4)=O)=N1)[O-].[Na+]

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

Soluble in DMSO

Shelf Life

>3 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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Pirenoxine sodium salt is an anti-cataract agent which is used in many asian countries under the name Catalin.

In vitro activity:

This study’s work was aimed at investigating in vitro the oxidative effects induced by subablative laser fluences and at demonstrating the protective effectiveness of pirenoxine. Comparative trials of subablative fluence on rabbit eyes with or without 10(-5) M pirenoxine were carried out. Superoxide anion (O(2)(-)), conjugated diene (CD), and thiobarbituric acid reagent substance (TBARS) formation were analyzed. Cellular death was evaluated by flow cytometry. Histological examinations were also performed. No appraisable differences in O(2)(-),CD,andTBARS formation were detected soon after irradiation, whereas they all increased following incubation. Pirenoxine inhibited such increases. Reference: J Photochem Photobiol B. 2005 Jan 14;78(1):35-42. https://pubmed.ncbi.nlm.nih.gov/15629247/

In vivo activity:

PRX (pirenoxine) at 1,000 μM significantly delayed UVC-induced turbidity formation compared to controls after 4 h of UVC exposure (p<0.05), but not in groups incubated with PRX concentrations of <1,000 μM. Results were further confirmed by SDS-PAGE. The absolute γ-crystallin turbidity induced by 4 h of UVC exposure was ameliorated in the presence of catalin equivalent to 1~100 μM PRX in a concentration-dependent manner. Samples with catalin-formulated vehicle only (CataV) and those containing PRX equivalent to 100 μM had a similar protective effect after 4 h of UVC exposure compared to the controls (p<0.05). PRX at 0.03, 0.1, and 0.3 μM significantly delayed 10 mM selenite- and calcium-induced turbidity formation compared to controls on days 0~4 (p<0.05). Catalin (equivalent to 32, 80, and 100 μM PRX) had an initial protective effect against selenite-induced lens protein turbidity on day 1 (p<0.05). Subcutaneous pretreatment with catalin (5 mg/kg) also statistically decreased the mean cataract scores in selenite-induced cataract rats on post-induction day 3 compared to the controls (1.3±0.2 versus 2.4±0.4; p<0.05). Reference: Mol Vis. 2011;17:1862-70. Epub 2011 Jul 12. https://pubmed.ncbi.nlm.nih.gov/21850160/

Preparing Stock Solutions

The following data is based on the product molecular weight 330.23 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. Hu CC, Liao JH, Hsu KY, Lin IL, Tsai MH, Wu WH, Wei TT, Huang YS, Chiu SJ, Chen HY, Wu SH, Wu TH. Role of pirenoxine in the effects of catalin on in vitro ultraviolet-induced lens protein turbidity and selenite-induced cataractogenesis in vivo. Mol Vis. 2011;17:1862-70. Epub 2011 Jul 12. PMID: 21850160; PMCID: PMC3144730. 2. Cantore M, Siano S, Coronnello M, Mazzetti L, Franchi-Micheli S, Boldrini E, Ciuffi M, Failli P. Pirenoxine prevents oxidative effects of argon fluoride excimer laser irradiation in rabbit corneas: biochemical, histological and cytofluorimetric evaluations. J Photochem Photobiol B. 2005 Jan 14;78(1):35-42. doi: 10.1016/j.jphotobiol.2004.09.005. PMID: 15629247.

In vitro protocol:

In vivo protocol:

1: Zhou Y, Hu Y, Zeng N, Ji Y, Dai X, Li P, Ma H, He Y. Noninvasive monitoring of Pirenoxine Sodium concentration in aqueous humor based on dual-wavelength iris imaging technique. Biomed Opt Express. 2011 Jan 5;2(2):231-42. doi: 10.1364/BOE.2.000231. PMID: 21339869; PMCID: PMC3038439. 2: Ueno A, Yamaoka S, Ito Y, Kotake T, Nakazawa Y, Nagai N. [Improvement of Dissolution Rate and Stability in a Pirenoxine Ophthalmic Suspension by the Bead Mill Methods]. Yakugaku Zasshi. 2017;137(5):635-641. Japanese. doi: 10.1248/yakushi.16-00267. PMID: 28458295. 3: Tsuneyoshi Y, Higuchi A, Negishi K, Tsubota K. Suppression of presbyopia progression with pirenoxine eye drops: experiments on rats and non-blinded, randomized clinical trial of efficacy. Sci Rep. 2017 Jul 28;7(1):6819. doi: 10.1038/s41598-017-07208-6. Erratum in: Sci Rep. 2020 Apr 16;10(1):6757. PMID: 28754903; PMCID: PMC5533700. 4: Xu T, Zhang J, Chi H, Cao F. Multifunctional properties of organic-inorganic hybrid nanocomposites based on chitosan derivatives and layered double hydroxides for ocular drug delivery. Acta Biomater. 2016 May;36:152-63. doi: 10.1016/j.actbio.2016.02.041. Epub 2016 Mar 3. PMID: 26940970. 5: Ciuffi M, Pisanello M, Pagliai G, Raimondi L, Franchi-Micheli S, Cantore M, Mazzetti L, Failli P. Antioxidant protection in cultured corneal cells and whole corneas submitted to UV-B exposure. J Photochem Photobiol B. 2003 Oct 15;71(1-3):59-68. doi: 10.1016/j.jphotobiol.2003.07.004. PMID: 14705640. 6: Ciuffi M, Neri S, Franchi-Micheli S, Failli P, Zilletti L, Moncelli MR, Guidelli R. Protective effect of pirenoxine and U74389F on induced lipid peroxidation in mammalian lenses. An in vitro, ex vivo and in vivo study. Exp Eye Res. 1999 Mar;68(3):347-59. doi: 10.1006/exer.1998.0612. PMID: 10079143. 7: Cantore M, Siano S, Coronnello M, Mazzetti L, Franchi-Micheli S, Boldrini E, Ciuffi M, Failli P. Pirenoxine prevents oxidative effects of argon fluoride excimer laser irradiation in rabbit corneas: biochemical, histological and cytofluorimetric evaluations. J Photochem Photobiol B. 2005 Jan 14;78(1):35-42. doi: 10.1016/j.jphotobiol.2004.09.005. PMID: 15629247. 8: Liao JH, Chen CS, Hu CC, Chen WT, Wang SP, Lin IL, Huang YH, Tsai MH, Wu TH, Huang FY, Wu SH. Ditopic complexation of selenite anions or calcium cations by pirenoxine: an implication for anti-cataractogenesis. Inorg Chem. 2011 Jan 3;50(1):365-77. doi: 10.1021/ic102151p. Epub 2010 Dec 7. PMID: 21138325. 9: Liao Z, Yu X, Yao Q, Yi P. Interaction between pirenoxine and bovine serum albumin in aqueous solution. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Aug 14;129:314-9. doi: 10.1016/j.saa.2014.03.057. Epub 2014 Apr 1. PMID: 24747854. 10: Sekimoto M, Imanaka Y, Kitano N, Ishizaki T, Takahashi O. Why are physicians not persuaded by scientific evidence? A grounded theory interview study. BMC Health Serv Res. 2006 Jul 27;6:92. doi: 10.1186/1472-6963-6-92. PMID: 16872522; PMCID: PMC1555581.