Arundic Acid | CAS#185517-21-9 | Astrocyte Modulating Agent

MedKoo Cat#: 524261 | Name: Arundic Acid

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Description:

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

Arundic Acid is is an astrocyte modulating agent, in acute ischemic stroke. It is a therapeutic agent for the treatment of neurodegenerative diseases including Alzheimer’s disease and Parkinson’s disease.

Chemical Structure

Arundic Acid

CAS#185517-21-9

Theoretical Analysis

MedKoo Cat#: 524261

Name: Arundic Acid

CAS#: 185517-21-9

Chemical Formula: C11H22O2

Exact Mass: 186.1619

Molecular Weight: 186.29

Elemental Analysis: C, 70.92; H, 11.90; O, 17.18

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
25mg	USD 950.00	2 Weeks

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Synonym

Arundic Acid; Arocyte; Cereact; MK-0724; MK 0724; MK0724; ONO-2506; ONO2506; ONO 2506; Proglia;

IUPAC/Chemical Name

(R)-2-propyloctanoic acid

InChi Key

YCYMCMYLORLIJX-SNVBAGLBSA-N

InChi Code

InChI=1S/C11H22O2/c1-3-5-6-7-9-10(8-4-2)11(12)13/h10H,3-9H2,1-2H3,(H,12,13)/t10-/m1/s1

SMILES Code

CCCCCC[C@H](C(=O)O)CCC

Appearance

Oil

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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Arundic acid (ONO-2506) is an astrocyte-modulating agent, which delays the expansion of cerebral infarcts by modulating the activation of astrocytes through inhibition of S-100β synthesis.

In vitro activity:

The results showed that arundic acid increased EAAT1 promoter activity in a concentration- and time-dependent manner (Fig. 1B and C). Arundic acid significantly increased EAAT1 promoter activity after 24 h treatments with concentrations at ≥ 25 μM (p<0.001). Accordingly, subsequent studies on EAAT1 promoter activity were carried out with 24 h treatments at 50 μM. The cell viability assay confirmed that arundic acid did not cause cytotoxicity at this concentration (Fig. 1D). Reference: Mol Neurobiol. 2018 Jun; 55(6): 5031–5046. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5964991/

In vivo activity:

S100B levels also increased in both ICH and ICH + AA (arundic acid) groups 72 h after injury compared to VEH (Fig. 5b, c), but the AA-treated rats had lower levels compared to the untreated group (F(2,29) = 77.718, p < 0.001; n = 8–12 per group). Seven days after injury, GFAP levels remained increased in the ICH group, but there was a reduction of the levels in the AA-treated animals (Fig. 6a, c), with no difference when compared to the VEH (F(2,26) = 4.982, p = 0.015; n = 8–10 per group). Similarly, S100B levels also remained high in the ICH group, but the AA-treated animals had a decrease in S100B levels compared to the untreated group (Fig. 6b, c), showing similar levels to the VEH group (F(2,26) = 3.781, p = 0.037; n = 8–10 per group). CD11b levels were also increased in both groups submitted to ICH compared to the VEH group 72 h after injury (Fig. 7a, c), demonstrating microglial/macrophage activation in the damaged striatum. The ICH + AA had lower levels compared to ICH group (F(2,28) = 36.928, p < 0.001; n = 8–12 per group). At 7 days, the ICH group had increased CD11b levels, while the AA-treated animals presented lower levels, similar to the Vehicle group (Fig. 7b, c) (F(2,26) = 5.089, p = 0.014; n = 8–10 per group). Reference: Cell Mol Neurobiol. 2020 Sep 11. https://pubmed.ncbi.nlm.nih.gov/32918255/

	Solvent	mg/mL	mM
Solubility
	DMSO	59.5	319.13
	DMF	10.0	53.68
	Ethanol	21.8	117.13
	Ethanol:PBS (pH 7.2) (1:2)	0.3	1.61

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 186.29 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. Vizuete AFK, de Lima Cordeiro J, Neves JD, Seady M, Grun LK, Barbé-Tuana FM, Leite MC, Netto CA, Gonçalves CA. Arundic acid (ONO-2526) inhibits stimulated-S100B secretion in inflammatory conditions. Neurosci Lett. 2021 Apr 23;751:135776. doi: 10.1016/j.neulet.2021.135776. Epub 2021 Mar 13. PMID: 33727126. 2. Karki P, Hong P, Johnson J Jr, Pajarillo E, Son DS, Aschner M, Lee EY. Arundic Acid Increases Expression and Function of Astrocytic Glutamate Transporter EAAT1 Via the ERK, Akt, and NF-κB Pathways. Mol Neurobiol. 2018 Jun;55(6):5031-5046. doi: 10.1007/s12035-017-0709-x. Epub 2017 Aug 15. PMID: 28812276; PMCID: PMC5964991. 3. Cordeiro JL, Neves JD, Nicola F, Vizuete AF, Sanches EF, Gonçalves CA, Netto CA. Arundic Acid (ONO-2506) Attenuates Neuroinflammation and Prevents Motor Impairment in Rats with Intracerebral Hemorrhage. Cell Mol Neurobiol. 2020 Sep 11. doi: 10.1007/s10571-020-00964-6. Epub ahead of print. PMID: 32918255. 4. Cordeiro JL, Neves JD, Vizuete AF, Aristimunha D, Pedroso TA, Sanches EF, Gonçalves CA, Netto CA. Arundic Acid (ONO-2506), an Inhibitor of S100B Protein Synthesis, Prevents Neurological Deficits and Brain Tissue Damage Following Intracerebral Hemorrhage in Male Wistar Rats. Neuroscience. 2020 Aug 1;440:97-112. doi: 10.1016/j.neuroscience.2020.05.030. Epub 2020 May 29. PMID: 32474054.

In vitro protocol:

In vivo protocol:

1. Cordeiro JL, Neves JD, Nicola F, Vizuete AF, Sanches EF, Gonçalves CA, Netto CA. Arundic Acid (ONO-2506) Attenuates Neuroinflammation and Prevents Motor Impairment in Rats with Intracerebral Hemorrhage. Cell Mol Neurobiol. 2020 Sep 11. doi: 10.1007/s10571-020-00964-6. Epub ahead of print. PMID: 32918255. 2. Cordeiro JL, Neves JD, Vizuete AF, Aristimunha D, Pedroso TA, Sanches EF, Gonçalves CA, Netto CA. Arundic Acid (ONO-2506), an Inhibitor of S100B Protein Synthesis, Prevents Neurological Deficits and Brain Tissue Damage Following Intracerebral Hemorrhage in Male Wistar Rats. Neuroscience. 2020 Aug 1;440:97-112. doi: 10.1016/j.neuroscience.2020.05.030. Epub 2020 May 29. PMID: 32474054.

1: Fernandes RA, Ingle AB. Arundic acid a potential neuroprotective agent: biological development and syntheses. Curr Med Chem. 2013;20(18):2315-29. doi: 10.2174/0929867311320180003. PMID: 23514413. 2: Cordeiro JL, Neves JD, Nicola F, Vizuete AF, Sanches EF, Gonçalves CA, Netto CA. Arundic Acid (ONO-2506) Attenuates Neuroinflammation and Prevents Motor Impairment in Rats with Intracerebral Hemorrhage. Cell Mol Neurobiol. 2022 Apr;42(3):739-751. doi: 10.1007/s10571-020-00964-6. Epub 2020 Sep 11. PMID: 32918255. 3: Asano T, Mori T, Shimoda T, Shinagawa R, Satoh S, Yada N, Katsumata S, Matsuda S, Kagamiishi Y, Tateishi N. Arundic acid (ONO-2506) ameliorates delayed ischemic brain damage by preventing astrocytic overproduction of S100B. Curr Drug Targets CNS Neurol Disord. 2005 Apr;4(2):127-42. doi: 10.2174/1568007053544084. PMID: 15857298. 4: Vizuete AFK, de Lima Cordeiro J, Neves JD, Seady M, Grun LK, Barbé-Tuana FM, Leite MC, Netto CA, Gonçalves CA. Arundic acid (ONO-2526) inhibits stimulated-S100B secretion in inflammatory conditions. Neurosci Lett. 2021 Apr 23;751:135776. doi: 10.1016/j.neulet.2021.135776. Epub 2021 Mar 13. PMID: 33727126. 5: Vizuete AFK, Leal MB, Moreira AP, Seady M, Taday J, Gonçalves CA. Arundic acid (ONO-2506) downregulates neuroinflammation and astrocyte dysfunction after status epilepticus in young rats induced by Li-pilocarpine. Prog Neuropsychopharmacol Biol Psychiatry. 2023 Apr 20;123:110704. doi: 10.1016/j.pnpbp.2022.110704. Epub 2022 Dec 21. PMID: 36565981. 6: Karki P, Hong P, Johnson J Jr, Pajarillo E, Son DS, Aschner M, Lee EY. Arundic Acid Increases Expression and Function of Astrocytic Glutamate Transporter EAAT1 Via the ERK, Akt, and NF-κB Pathways. Mol Neurobiol. 2018 Jun;55(6):5031-5046. doi: 10.1007/s12035-017-0709-x. Epub 2017 Aug 15. PMID: 28812276; PMCID: PMC5964991. 7: Yanagisawa M, Aida T, Takeda T, Namekata K, Harada T, Shinagawa R, Tanaka K. Arundic acid attenuates retinal ganglion cell death by increasing glutamate/aspartate transporter expression in a model of normal tension glaucoma. Cell Death Dis. 2015 Mar 19;6(3):e1693. doi: 10.1038/cddis.2015.45. PMID: 25789968; PMCID: PMC4385923. 8: Cordeiro JL, Neves JD, Vizuete AF, Aristimunha D, Pedroso TA, Sanches EF, Gonçalves CA, Netto CA. Arundic Acid (ONO-2506), an Inhibitor of S100B Protein Synthesis, Prevents Neurological Deficits and Brain Tissue Damage Following Intracerebral Hemorrhage in Male Wistar Rats. Neuroscience. 2020 Aug 1;440:97-112. doi: 10.1016/j.neuroscience.2020.05.030. Epub 2020 May 29. PMID: 32474054. 9: Kato H, Kurosaki R, Oki C, Araki T. Arundic acid, an astrocyte-modulating agent, protects dopaminergic neurons against MPTP neurotoxicity in mice. Brain Res. 2004 Dec 24;1030(1):66-73. doi: 10.1016/j.brainres.2004.09.046. PMID: 15567338. 10: Hao MM, Capoccia E, Cirillo C, Boesmans W, Vanden Berghe P. Arundic Acid Prevents Developmental Upregulation of S100B Expression and Inhibits Enteric Glial Development. Front Cell Neurosci. 2017 Feb 23;11:42. doi: 10.3389/fncel.2017.00042. PMID: 28280459; PMCID: PMC5322270. 11: Miyamoto Y, Nakahara M, Motoyama K, Ishiguro T, Oda Y, Yamanoi T, Okamoto I, Yagi A, Nishimura H, Hirayama F, Uekama K, Arima H. Improvement of some physicochemical properties of arundic acid, (R)-(-)-2-propyloctanonic acid, by complexation with hydrophilic cyclodextrins. Int J Pharm. 2011 Jul 15;413(1-2):63-72. doi: 10.1016/j.ijpharm.2011.04.022. Epub 2011 Apr 21. PMID: 21540089. 12: Vizuete AFK, Fróes F, Seady M, Zanotto C, Bobermin LD, Roginski AC, Wajner M, Quincozes-Santos A, Gonçalves CA. Early effects of LPS-induced neuroinflammation on the rat hippocampal glycolytic pathway. J Neuroinflammation. 2022 Oct 11;19(1):255. doi: 10.1186/s12974-022-02612-w. PMID: 36221097; PMCID: PMC9552490. 13: Mori T, Town T, Tan J, Yada N, Horikoshi Y, Yamamoto J, Shimoda T, Kamanaka Y, Tateishi N, Asano T. Arundic Acid ameliorates cerebral amyloidosis and gliosis in Alzheimer transgenic mice. J Pharmacol Exp Ther. 2006 Aug;318(2):571-8. doi: 10.1124/jpet.106.105171. Epub 2006 May 18. PMID: 16709678. 14: Fukushi I, Takeda K, Yokota S, Hasebe Y, Sato Y, Pokorski M, Horiuchi J, Okada Y. Effects of arundic acid, an astrocytic modulator, on the cerebral and respiratory functions in severe hypoxia. Respir Physiol Neurobiol. 2016 Jun;226:24-9. doi: 10.1016/j.resp.2015.11.011. Epub 2015 Nov 22. PMID: 26592145. 15: Ishibashi H, Pettigrew LC, Funakoshi Y, Hiramatsu M. Pharmacokinetics of arundic acid, an astrocyte modulating agent, in acute ischemic stroke. J Clin Pharmacol. 2007 Apr;47(4):445-52. doi: 10.1177/0091270006299090. PMID: 17389553. 16: Mari C, Odorcyk FK, Sanches EF, Wartchow KM, Martini AP, Nicola F, Zanotto C, Wyse AT, Gonçalves CA, Netto CA. Arundic acid administration protects astrocytes, recovers histological damage and memory deficits induced by neonatal hypoxia ischemia in rats. Int J Dev Neurosci. 2019 Aug;76:41-51. doi: 10.1016/j.ijdevneu.2019.06.003. Epub 2019 Jun 13. PMID: 31202867. 17: Keshavarz M, Farrokhi MR, Amiri A, Hosseini M. The contribution of S100B to the glioprotective effects of valproic and arundic acids. Iran J Basic Med Sci. 2019 May;22(5):557-562. doi: 10.22038/ijbms.2019.29852.7204. PMID: 31217937; PMCID: PMC6556503. 18: Oki C, Watanabe Y, Yokoyama H, Shimoda T, Kato H, Araki T. Delayed treatment with arundic acid reduces the MPTP-induced neurotoxicity in mice. Cell Mol Neurobiol. 2008 May;28(3):417-30. doi: 10.1007/s10571-007-9241-2. Epub 2008 Jan 17. PMID: 18204968. 19: Cui W, Wang M, Maegawa H, Teranishi Y, Kawada N. Inhibition of the activation of hepatic stellate cells by arundic acid via the induction of cytoglobin. Biochem Biophys Res Commun. 2012 Aug 31;425(3):642-8. doi: 10.1016/j.bbrc.2012.07.126. Epub 2012 Jul 28. PMID: 22850540. 20: Hanada M, Shinjo R, Miyagi M, Yasuda T, Tsutsumi K, Sugiura Y, Imagama S, Ishiguro N, Matsuyama Y. Arundic acid (ONO-2506) inhibits secondary injury and improves motor function in rats with spinal cord injury. J Neurol Sci. 2014 Feb 15;337(1-2):186-92. doi: 10.1016/j.jns.2013.12.008. Epub 2013 Dec 13. PMID: 24360553.

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