SEN-12333 | CAS#874450-44-9 | alpha(7) nAChR agonist

SEN-12333
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 556020

CAS#: 874450-44-9

Description: SEN-12333, also known as WAY-31753, is is a selective agonist of the alpha(7) nAChR (EC50 = 1.6 μM, Ki = 260 nM at rat α7 nAChRs). SEN-12333 displayed excellent in vitro and in vivo profiles, excellent brain penetration and oral bioavailability, and demonstrates in vivo efficacy in multiple behavioural cognition models.

Chemical Structure

SEN-12333

CAS# 874450-44-9

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 556020
Name: SEN-12333
CAS#: 874450-44-9
Chemical Formula: C20H25N3O2
Exact Mass: 339.19
Molecular Weight: 339.439
Elemental Analysis: C, 70.77; H, 7.42; N, 12.38; O, 9.43

Price and Availability

Size	Price	Availability
50mg	USD 450	2 Weeks
100mg	USD 750	2 Weeks
200mg	USD 1350	2 Weeks
500mg	USD 2650	2 Weeks
1g	USD 3650	2 Weeks
2g	USD 5950	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: SEN 12333; SEN-12333; SEN12333; WAY-31753; WAY31753; WAY 31753;

IUPAC/Chemical Name: N-[4-(3-pyridinyl)phenyl]-4-morpholinepentanamide

InChi Key: XCHIZTUBUXZESJ-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H25N3O2/c24-20(5-1-2-11-23-12-14-25-15-13-23)22-19-8-6-17(7-9-19)18-4-3-10-21-16-18/h3-4,6-10,16H,1-2,5,11-15H2,(H,22,24)

SMILES Code: O=C(NC1=CC=C(C2=CC=CN=C2)C=C1)CCCCN3CCOCC3

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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

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Biological target:	α7 nicotinic acetylcholine receptor (nAChR) agonist.
In vitro activity:	Alpha 7 nAChRs are expressed in brain regions associated with cognitive function, regulate cholinergic neurotransmission and have been shown to be down regulated in both schizophrenia and Alzheimer's disease. Herein a novel, potent small molecule agonist of the alpha 7 nAChR, SEN12333/WAY-317538 was reported. This compound is a selective agonist of the alpha(7) nAChR with excellent in vitro and in vivo profiles, excellent brain penetration and oral bioavailability, and demonstrates in vivo efficacy in multiple behavioural cognition models. The SAR and biological evaluation of this series of compounds are discussed. Reference: Haydar SN, Ghiron C, Bettinetti L, Bothmann H, Comery TA, Dunlop J, La Rosa S, Micco I, Pollastrini M, Quinn J, Roncarati R, Scali C, Valacchi M, Varrone M, Zanaletti R. SAR and biological evaluation of SEN12333/WAY-317538: Novel alpha 7 nicotinic acetylcholine receptor agonist. Bioorg Med Chem. 2009 Jul 15;17(14):5247-58. doi: 10.1016/j.bmc.2009.05.040. Epub 2009 May 21. Erratum in: Bioorg Med Chem. 2010 Jan 15;18(2):985. PMID: 19515567.
In vivo activity:	Alpha 7 nAChRs are expressed in brain regions associated with cognitive function, regulate cholinergic neurotransmission and have been shown to be down regulated in both schizophrenia and Alzheimer's disease. Herein a novel, potent small molecule agonist of the alpha 7 nAChR, SEN12333/WAY-317538 was reported. This compound is a selective agonist of the alpha(7) nAChR with excellent in vitro and in vivo profiles, excellent brain penetration and oral bioavailability, and demonstrates in vivo efficacy in multiple behavioural cognition models. The SAR and biological evaluation of this series of compounds are discussed. Reference: Haydar SN, Ghiron C, Bettinetti L, Bothmann H, Comery TA, Dunlop J, La Rosa S, Micco I, Pollastrini M, Quinn J, Roncarati R, Scali C, Valacchi M, Varrone M, Zanaletti R. SAR and biological evaluation of SEN12333/WAY-317538: Novel alpha 7 nicotinic acetylcholine receptor agonist. Bioorg Med Chem. 2009 Jul 15;17(14):5247-58. doi: 10.1016/j.bmc.2009.05.040. Epub 2009 May 21. Erratum in: Bioorg Med Chem. 2010 Jan 15;18(2):985. PMID: 19515567.

Preparing Stock Solutions

The following data is based on the product molecular weight 339.44 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:	Haydar SN, Ghiron C, Bettinetti L, Bothmann H, Comery TA, Dunlop J, La Rosa S, Micco I, Pollastrini M, Quinn J, Roncarati R, Scali C, Valacchi M, Varrone M, Zanaletti R. SAR and biological evaluation of SEN12333/WAY-317538: Novel alpha 7 nicotinic acetylcholine receptor agonist. Bioorg Med Chem. 2009 Jul 15;17(14):5247-58. doi: 10.1016/j.bmc.2009.05.040. Epub 2009 May 21. Erratum in: Bioorg Med Chem. 2010 Jan 15;18(2):985. PMID: 19515567.
In vitro protocol:	Haydar SN, Ghiron C, Bettinetti L, Bothmann H, Comery TA, Dunlop J, La Rosa S, Micco I, Pollastrini M, Quinn J, Roncarati R, Scali C, Valacchi M, Varrone M, Zanaletti R. SAR and biological evaluation of SEN12333/WAY-317538: Novel alpha 7 nicotinic acetylcholine receptor agonist. Bioorg Med Chem. 2009 Jul 15;17(14):5247-58. doi: 10.1016/j.bmc.2009.05.040. Epub 2009 May 21. Erratum in: Bioorg Med Chem. 2010 Jan 15;18(2):985. PMID: 19515567.
In vivo protocol:	Haydar SN, Ghiron C, Bettinetti L, Bothmann H, Comery TA, Dunlop J, La Rosa S, Micco I, Pollastrini M, Quinn J, Roncarati R, Scali C, Valacchi M, Varrone M, Zanaletti R. SAR and biological evaluation of SEN12333/WAY-317538: Novel alpha 7 nicotinic acetylcholine receptor agonist. Bioorg Med Chem. 2009 Jul 15;17(14):5247-58. doi: 10.1016/j.bmc.2009.05.040. Epub 2009 May 21. Erratum in: Bioorg Med Chem. 2010 Jan 15;18(2):985. PMID: 19515567.

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1: Xie J, Zhao T, Liu Y. Sonic hedgehog regulates the pathfinding of descending serotonergic axons in hindbrain in collaboration with Wnt5a and secreted frizzled-related protein 1. Int J Dev Neurosci. 2018 May;66:24-32. doi: 10.1016/j.ijdevneu.2017.11.006. Epub 2017 Nov 28. PMID: 29196093.

2: Beinat C, Banister SD, Herrera M, Kassiou M. The Recent Development of α7 Nicotinic Acetylcholine Receptor (nAChR) Ligands as Therapeutic Candidates for the Treatment of Central Nervous System (CNS) Diseases. Curr Pharm Des. 2016;22(14):2134-51. doi: 10.2174/1381612822666160127114125. PMID: 26818858.

3: Beinat C, Reekie T, Banister SD, O'Brien-Brown J, Xie T, Olson TT, Xiao Y, Harvey A, O'Connor S, Coles C, Grishin A, Kolesik P, Tsanaktsidis J, Kassiou M. Structure-activity relationship studies of SEN12333 analogues: determination of the optimal requirements for binding affinities at α7 nAChRs through incorporation of known structural motifs. Eur J Med Chem. 2015 May 5;95:277-301. doi: 10.1016/j.ejmech.2015.03.025. Epub 2015 Mar 14. PMID: 25827398.

4: Beinat C, Reekie T, Hibbs D, Xie T, Olson TT, Xiao Y, Harvey A, O'Connor S, Coles C, Tsanaktsidis J, Kassiou M. Investigations of amide bond variation and biaryl modification in analogues of α7 nAChR agonist SEN12333. Eur J Med Chem. 2014 Sep 12;84:200-5. doi: 10.1016/j.ejmech.2014.07.029. Epub 2014 Jul 9. PMID: 25019477.

5: Beinat C, Banister SD, van Prehn S, Doddareddy MR, Hibbs D, Sako M, Chebib M, Tran T, Al-Muhtasib N, Xiao Y, Kassiou M. Consequences of linker length alteration of the α7 nicotinic acetylcholine receptor (nAChR) agonist, SEN12333. Bioorg Med Chem Lett. 2012 Apr 1;22(7):2380-4. doi: 10.1016/j.bmcl.2012.02.052. Epub 2012 Feb 24. PMID: 22410083.

6: Haydar SN, Ghiron C, Bettinetti L, Bothmann H, Comery TA, Dunlop J, La Rosa S, Micco I, Pollastrini M, Quinn J, Roncarati R, Scali C, Valacchi M, Varrone M, Zanaletti R. SAR and biological evaluation of SEN12333/WAY-317538: Novel alpha 7 nicotinic acetylcholine receptor agonist. Bioorg Med Chem. 2009 Jul 15;17(14):5247-58. doi: 10.1016/j.bmc.2009.05.040. Epub 2009 May 21. Erratum in: Bioorg Med Chem. 2010 Jan 15;18(2):985. PMID: 19515567.

7: Roncarati R, Scali C, Comery TA, Grauer SM, Aschmi S, Bothmann H, Jow B, Kowal D, Gianfriddo M, Kelley C, Zanelli U, Ghiron C, Haydar S, Dunlop J, Terstappen GC. Procognitive and neuroprotective activity of a novel alpha7 nicotinic acetylcholine receptor agonist for treatment of neurodegenerative and cognitive disorders. J Pharmacol Exp Ther. 2009 May;329(2):459-68. doi: 10.1124/jpet.108.150094. Epub 2009 Feb 17. PMID: 19223665.

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