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MedKoo Cat#: 565388 | Name: Pirenoxine (free base)
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Description:

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

Pirenoxine (free base), also known as Catalin, is an anti-cataractogenesis agent which interacts with selenite or calcium ions that have been proven as factors leading to the formation of lens cataract.

Chemical Structure

Pirenoxine (free base)
Pirenoxine (free base)
CAS#1043-21-6 (free base)

Theoretical Analysis

MedKoo Cat#: 565388

Name: Pirenoxine (free base)

CAS#: 1043-21-6 (free base)

Chemical Formula: C16H8N2O5

Exact Mass: 308.0433

Molecular Weight: 308.25

Elemental Analysis: C, 62.34; H, 2.62; N, 9.09; O, 25.95

Price and Availability

Size Price Availability Quantity
1mg USD 400.00
2mg USD 580.00
10mg USD 900.00
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Related CAS #
1043-21-6 (free base) 51410-30-1 (salt)
Synonym
PRX; Catalin; Pirenoxine
IUPAC/Chemical Name
1-Hydroxy-5-oxo-5H-pyrido[3,2-a]phenoxazine-3-carboxylic acid
InChi Key
OKPNYGAWTYOBFZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H8N2O5/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)
SMILES Code
O=C(C1=CC(O)=C2C(C(C=C3OC4=C(N=C32)C=CC=C4)=O)=N1)O
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 (Catalin K) is a potent antioxidant.
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 308.25 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. 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:
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 vivo 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.
1: Upaphong P, Thonusin C, Choovuthayakorn J, Chattipakorn N, Chattipakorn SC. The Possible Positive Mechanisms of Pirenoxine in Cataract Formation. Int J Mol Sci. 2022 Aug 21;23(16):9431. doi: 10.3390/ijms23169431. PMID: 36012695; PMCID: PMC9408903. 2: Tang CF, Gao Y, Gulibairemu Y, Mao Y, Li YJ, Wang YD, Gu ZY. Anti-cataract effects of Dajizhi (Euphorbium) eye drops on selenite-induced cataracts in rat. J Tradit Chin Med. 2021 Oct;41(5):747-752. doi: 10.19852/j.cnki.jtcm.2021.05.009. PMID: 34708633. 3: Pearson A, Munn Z, Coiera E. Catalin Tufanaru, 1970-2021. JBI Evid Synth. 2021 Sep 1;19(9):2050-2051. doi: 10.11124/JBIES-21-00318. PMID: 34518503. 4: Tsuneyoshi Y, Higuchi A, Negishi K, Tsubota K. Author Correction: Suppression of presbyopia progression with pirenoxine eye drops: experiments on rats and non-blinded, randomized clinical trial of efficacy. Sci Rep. 2020 Apr 16;10(1):6757. doi: 10.1038/s41598-020-62436-7. Erratum for: Sci Rep. 2017 Jul 28;7(1):6819. doi: 10.1038/s41598-017-07208-6. PMID: 32296100; PMCID: PMC7160192. 5: Baig AM, Katyara P, Khaleeq A, Nazim F. Repurposing drugs: Ca2+ ion dependency that can be exploited to treat keratitis caused by Acanthamoeba castellanii. Eye (Lond). 2019 Nov;33(11):1823-1825. doi: 10.1038/s41433-019-0597-6. Epub 2019 Sep 25. PMID: 31554952; PMCID: PMC7002657. 6: Xu T, Xu X, Gu Y, Fang L, Cao F. Functional intercalated nanocomposites with chitosan-glutathione-glycylsarcosine and layered double hydroxides for topical ocular drug delivery. Int J Nanomedicine. 2018 Feb 13;13:917-937. doi: 10.2147/IJN.S148104. PMID: 29491707; PMCID: PMC5815481. 7: 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. doi: 10.1038/s41598-020-62436-7. PMID: 28754903; PMCID: PMC5533700. 8: 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. 9: Chi H, Gu Y, Xu T, Cao F. Multifunctional organic-inorganic hybrid nanoparticles and nanosheets based on chitosan derivative and layered double hydroxide: cellular uptake mechanism and application for topical ocular drug delivery. Int J Nanomedicine. 2017 Feb 28;12:1607-1620. doi: 10.2147/IJN.S129311. PMID: 28280329; PMCID: PMC5339005. 10: 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. 11: Fang H, Hu X, Wang M, Wan W, Yang Q, Sun X, Gu Q, Gao X, Wang Z, Gu L, Oliver Chen CY, Wei X. Anti-osmotic and antioxidant activities of gigantol from Dendrobium aurantiacum var. denneanum against cataractogenesis in galactosemic rats. J Ethnopharmacol. 2015 Aug 22;172:238-46. doi: 10.1016/j.jep.2015.06.034. Epub 2015 Jun 25. PMID: 26119284. 12: 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. 13: 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. 14: 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. 15: 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. 16: Polunin GS, Makarova IA, Bubnova IA. [Efficacy of catalin eyed drops in age- related cataract agents]. Vestn Oftalmol. 2010 Jan-Feb;126(1):36-9. Russian. PMID: 20645574. 17: 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. 18: Kociecki J, Załecki K, Wasiewicz-Rager J, Pecold K. Ocena skuteczności preparatu Catalin--kropli ocznych u pacjentów z zaćma przedstarcza i starcza [Evaluation of effectiveness of Catalin eyedrops in patients with presenile and senile cataract]. Klin Oczna. 2004;106(6):778-82. Polish. PMID: 15787181. 19: 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. 20: Inui S, Ozawa K, Song M, Itami S, Katayama I. Contact dermatitis due to pirfenoxone. Contact Dermatitis. 2004 Jun;50(6):375-6. doi: 10.1111/j.0105-1873.2004.0350c.x. PMID: 15274732.

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