Edonerpic maleate
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MedKoo CAT#: 319579

CAS#: 519187-97-4 (maleate)

Description: 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

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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: 407.481
Elemental Analysis: C, 58.95; H, 6.18; N, 3.44; O, 23.56; S, 7.87

Price and Availability

Size Price Availability Quantity
25.0mg USD 150.0 Same day
50.0mg USD 250.0 Same day
100.0mg USD 450.0 Same day
200.0mg USD 750.0 Same day
500.0mg USD 1650.0 Same day
1.0g USD 2950.0 Same day
2.0g USD 4250.0 Same day
5.0g USD 6950.0 2 weeks
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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

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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 90.5 222.1
Ethanol 40.0 98.16
Water 90.5 222.1

Preparing Stock Solutions

The following data is based on the product molecular weight 407.481 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. 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: 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.
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.

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1: Page SJ, Murray C, Hermann V, Levine P. Retention of motor changes in chronic
stroke survivors who were administered mental practice. Arch Phys Med Rehabil.
2011 Nov;92(11):1741-5. doi: 10.1016/j.apmr.2011.06.009. Epub 2011 Aug 31. PubMed
PMID: 21880300; PubMed Central PMCID: PMC3257856.

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. eCollection 2011. PubMed PMID: 21629767; PubMed Central
PMCID: PMC3099362.

3: Kawasaki T, Ago Y, Kitao T, Nashida T, Takagi A, Takuma K, Matsuda T. A
neuroprotective agent, T-817MA (1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}
azetidin-3-ol maleate), prevents
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced neurotoxicity in mice.
Neuropharmacology. 2008 Oct;55(5):654-60. doi: 10.1016/j.neuropharm.2008.05.032.
Epub 2008 Jun 5. PubMed PMID: 18573265.



Additional Information

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