Edonerpic maleate | T-817 | CAS#519187-23-6 | 519187-97-4 | neuroprotectant

MedKoo Cat#: 319579 | Name: Edonerpic maleate

Description:

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

Edonerpic, also known as T-817, is a neuroprotectant. Edonerpic is a candidate therapeutic agent for Alzheimer's disease that inhibits oxidative stress and nitric oxide-induced neurotoxicity and acts as a neurotrophic factor. Edonerpic protects against MPTP-induced neurotoxicity by blocking lipid peroxidation in the SNc, and imply that this compound may be useful for treating neurodegenerative disorders related to oxidative stress, such as Parkinson's disease.

Chemical Structure

Edonerpic maleate

CAS#519187-97-4 (maleate)

Theoretical Analysis

MedKoo Cat#: 319579

Name: Edonerpic maleate

CAS#: 519187-97-4 (maleate)

Chemical Formula: C20H25NO6S

Exact Mass: 291.1293

Molecular Weight: 407.48

Elemental Analysis: C, 58.95; H, 6.18; N, 3.44; O, 23.56; S, 7.87

Price and Availability

Size	Price	Availability
25mg	USD 150.00	Ready to ship
50mg	USD 250.00	Ready to ship
100mg	USD 450.00	Ready to ship
200mg	USD 750.00	Ready to ship
500mg	USD 1,650.00	Ready to ship
1g	USD 2,950.00	Ready to ship
2g	USD 4,250.00	Ready to ship

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Related CAS #

519187-23-6 (free base) 519187-97-4 (maleate)

Synonym

T-817 maleate; T-817; T 817; T817; J2.179.155E; T-817MA; Edonerpic; Edonerpic maleate

IUPAC/Chemical Name

1-(3-(2-(benzo[b]thiophen-5-yl)ethoxy)propyl)azetidin-3-ol maleate

InChi Key

RLUCYBFCLXANSO-BTJKTKAUSA-N

InChi Code

InChI=1S/C16H21NO2S.C4H4O4/c18-15-11-17(12-15)6-1-7-19-8-4-13-2-3-16-14(10-13)5-9-20-16;5-3(6)1-2-4(7)8/h2-3,5,9-10,15,18H,1,4,6-8,11-12H2;1-2H,(H,5,6)(H,7,8)/b;2-1-

SMILES Code

OC1CN(CCCOCCC2=CC=C3C(C=CS3)=C2)C1.O=C(O)/C=C\C(O)=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, 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

More Info

Related CAS# CAS#519187-23-6 (t Edonerpic free base); CAS#519187-97-4 (t Edonerpic maleate).

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A8T05K29

QC Data

View QC data: current batch, Lot#A8T05K29

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Edonerpic maleate is a novel neurotrophic agent which can inhibit amyloid-β peptides (Aβ).

In vitro activity:

Edonerpic maleate inhibited peak calcium current density (p = 0.0426, Mann–Whitney test, Figure 1(e)) compared to 0.1% DMSO-treated controls neurons but had no effect on activation (Figure 1(f)) or inactivation (Figure 1(g)) properties of these channels. These results show that edonerpic maleate can decrease the function of voltage-gated calcium channels in DRG sensory neurons, in a manner similar to results obtained by uncoupling CRMP2 from CaV2.2 using decoy peptides. Next, this study tested if edonerpic maleate could inhibit the voltage-gated sodium channels. Cultured DRG neurons were treated overnight with 20 µM of edonerpic maleate prior to sodium current recordings (Figure 1(h)). In these experiments, neurons treated with edonerpic maleate had increased peak sodium current density compared to 0.1% DMSO-treated controls (p = 0.0348, Mann–Whitney test, Figure 1(i)). Activation and inactivation properties of voltage-gated sodium channels were unchanged (Figure 1(j–k)). These results are in diametric opposition to previous findings which demonstrated maintenance, not augmentation, of sodium channel current density by CRMP2. Reference: Channels (Austin). 2019; 13(1): 498–504. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6833970/

In vivo activity:

To study the potential effects of T-817MA (Edonerpic) on tau neuropathology, squids received an oral dose of T-817MA as described in the Section “Materials and Methods”. Electrophysiologically, as shown in Figure 1B no significant changes in the amplitude or time course of the pre- or post-synaptic potentials were observed. Further, ultrastructural studies in synapses used for the electrophysiological experiments demonstrated the number of docked vesicles recovered to the normal range in h-tau42/T-817MA squid (31 active zones in six synapses; 10.0 ± 0.6) compared to control synapses (10.1 ± 0.7), with the presence of normal CCV profiles (3.9 ± 0.4). Also clear was a significant reduction, of electron dense vesicles clusters and electron dense active zones (see Table 1; Figure 4). It is thus concluded that T-817MA prevented the h-tau42 dependent synaptic vesicle clustering, indicating a close relation between such morphology and the synaptic transmitter release block observed electrophysiologically. Finally squid pretreated with T-817MA showed a significantly reduced signal of intra-axonal h-tau42 phosphorylation, as detected by AT8 immunohistochemistry (Figure 3). Reference: Front Synaptic Neurosci. 2011; 3: 3. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3099362/

	Solvent	mg/mL	mM
Solubility
	DMSO	90.5	222.10
	Ethanol	40.0	98.16
	Water	90.5	222.10

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 407.48 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. Moutal A, Shan Z, Miranda VG, François-Moutal L, Madura CL, Khanna M, Khanna R. Evaluation of edonerpic maleate as a CRMP2 inhibitor for pain relief. Channels (Austin). 2019 Dec;13(1):498-504. doi: 10.1080/19336950.2019.1684608. PMID: 31680630; PMCID: PMC6833970. 2. Takahashi T. Novel synaptic plasticity enhancer drug to augment functional recovery with rehabilitation. Curr Opin Neurol. 2019 Dec;32(6):822-827. doi: 10.1097/WCO.0000000000000748. PMID: 31567431; PMCID: PMC6855342. 3. Moreno H, Choi S, Yu E, Brusco J, Avila J, Moreira JE, Sugimori M, Llinás RR. Blocking Effects of Human Tau on Squid Giant Synapse Transmission and Its Prevention by T-817 MA. Front Synaptic Neurosci. 2011 May 17;3:3. doi: 10.3389/fnsyn.2011.00003. PMID: 21629767; PMCID: PMC3099362.

In vitro protocol:

In vivo protocol:

1. Takahashi T. Novel synaptic plasticity enhancer drug to augment functional recovery with rehabilitation. Curr Opin Neurol. 2019 Dec;32(6):822-827. doi: 10.1097/WCO.0000000000000748. PMID: 31567431; PMCID: PMC6855342. 2. Moreno H, Choi S, Yu E, Brusco J, Avila J, Moreira JE, Sugimori M, Llinás RR. Blocking Effects of Human Tau on Squid Giant Synapse Transmission and Its Prevention by T-817 MA. Front Synaptic Neurosci. 2011 May 17;3:3. doi: 10.3389/fnsyn.2011.00003. PMID: 21629767; PMCID: PMC3099362.

1: Chen T, Yang LK, Ai P, Zhu J, Hang CH, Wang YH. Edonerpic maleate regulates glutamate receptors through CRMP2- and Arc-mediated mechanisms in response to brain trauma. Cell Death Discov. 2022 Mar 4;8(1):95. doi: 10.1038/s41420-022-00901-0. PMID: 35246523; PMCID: PMC8897457. 2: Moutal A, Shan Z, Miranda VG, François-Moutal L, Madura CL, Khanna M, Khanna R. Evaluation of edonerpic maleate as a CRMP2 inhibitor for pain relief. Channels (Austin). 2019 Dec;13(1):498-504. doi: 10.1080/19336950.2019.1684608. PMID: 31680630; PMCID: PMC6833970. 3: Pines AR, Sattur MG, Abi-Aad KR, Bendok BR. Edonerpic Maleate: A Promising Pharmacological Agent for Stroke Recovery. Neurosurgery. 2019 Jan 1;84(1):E3-E4. doi: 10.1093/neuros/nyy397. PMID: 30551191. 4: Schneider LS, Thomas RG, Hendrix S, Rissman RA, Brewer JB, Salmon DP, Oltersdorf T, Okuda T, Feldman HH; Alzheimer’s Disease Cooperative Study TCAD Study Group. Safety and Efficacy of Edonerpic Maleate for Patients With Mild to Moderate Alzheimer Disease: A Phase 2 Randomized Clinical Trial. JAMA Neurol. 2019 Nov 1;76(11):1330-1339. doi: 10.1001/jamaneurol.2019.1868. PMID: 31282954; PMCID: PMC6618817. 5: Abe H, Jitsuki S, Nakajima W, Murata Y, Jitsuki-Takahashi A, Katsuno Y, Tada H, Sano A, Suyama K, Mochizuki N, Komori T, Masuyama H, Okuda T, Goshima Y, Higo N, Takahashi T. CRMP2-binding compound, edonerpic maleate, accelerates motor function recovery from brain damage. Science. 2018 Apr 6;360(6384):50-57. doi: 10.1126/science.aao2300. PMID: 29622647. 6: Takahashi T. Novel synaptic plasticity enhancer drug to augment functional recovery with rehabilitation. Curr Opin Neurol. 2019 Dec;32(6):822-827. doi: 10.1097/WCO.0000000000000748. PMID: 31567431; PMCID: PMC6855342. 7: Khanna R, Moutal A, Perez-Miller S, Chefdeville A, Boinon L, Patek M. Druggability of CRMP2 for Neurodegenerative Diseases. ACS Chem Neurosci. 2020 Sep 2;11(17):2492-2505. doi: 10.1021/acschemneuro.0c00307. Epub 2020 Aug 4. PMID: 32693579. 8: Jitsuki S. [CRMP2 binding compound accelerates functional recovery from central nervous system damage]. Nihon Yakurigaku Zasshi. 2022;157(4):244-247. Japanese. doi: 10.1254/fpj.22011. PMID: 35781453.