Siramesine fumarate salt

Modify Date: 2025-08-26 18:53:23

Siramesine fumarate salt Structure
Siramesine fumarate salt structure
Common Name Siramesine fumarate salt
CAS Number 163630-79-3 Molecular Weight 570.65
Density N/A Boiling Point N/A
Molecular Formula C34H35FN2O5 Melting Point N/A
MSDS USA Flash Point N/A

 Use of Siramesine fumarate salt


Siramesine (Lu 28-179) fumarate is a potent sigma-2 receptor agonist. Siramesine fumarate has a subnanomolar affinity for sigma-2 receptors (IC50=0.12?nM) and exhibits a 140-fold selectivity for sigma-2 receptors over sigma-1 receptors (IC50=17?nM). Siramesine fumarate triggers cell death through destabilisation of mitochondria, but not lysosomes. Anti-cancer activity[1][2][3].

 Names

Name 1'-{4-[1-(4-Fluorophenyl)-1H-indol-3-yl]butyl}-3H-spiro[2-benzofuran-1,4'-piperidine] (2E)-2-butenedioate (1:1)
Synonym More Synonyms

 Siramesine fumarate salt Biological Activity

Description Siramesine (Lu 28-179) fumarate is a potent sigma-2 receptor agonist. Siramesine fumarate has a subnanomolar affinity for sigma-2 receptors (IC50=0.12?nM) and exhibits a 140-fold selectivity for sigma-2 receptors over sigma-1 receptors (IC50=17?nM). Siramesine fumarate triggers cell death through destabilisation of mitochondria, but not lysosomes. Anti-cancer activity[1][2][3].
Related Catalog
In Vitro Siramesine fumarate displays the binding affinities: IC50 (sigma 1)=17 nM, IC50 (sigma 2)=0.12 nM, IC50 (5-HT1A)=21000 nM, IC50 (5-HT1A)=2000 nM, IC50 (D2)=800 nM, IC50 (alpha 1)=330 nM[1]. Siramesine fumarate (0-50μM; 8 hours) induces cell death in various cell lines (HaCaT, Hsc-4, HeLa and MCF-7, neuroblastoma cell line SH-SY5Y and glioblastoma cell line U-87MG)[2]. Siramesine fumarate (0-40 μM; 2-48 hours) activates caspases in HaCaT and in U-87MG cells[2].
References

[1]. Perregaard J, et al. Sigma ligands with subnanomolar affinity and preference for the sigma 2 binding site. 1. 3-(omega-aminoalkyl)-1H-indoles. J Med Chem. 1995;38(11):1998-2008.  

[2]. Česen MH, et al. Siramesine triggers cell death through destabilisation of mitochondria, but not lysosomes. Cell Death Dis. 2013;4(10):e818. Published 2013 Oct 3.  

[3]. Ostenfeld MS, et al. Anti-cancer agent siramesine is a lysosomotropic detergent that induces cytoprotective autophagosome accumulation. Autophagy. 2008;4(4):487-499.  

 Chemical & Physical Properties

Molecular Formula C34H35FN2O5
Molecular Weight 570.65
Exact Mass 570.252991
InChIKey VONJQLKJOYOVBE-WLHGVMLRSA-N
SMILES Fc1ccc(-n2cc(CCCCN3CCC4(CC3)OCc3ccccc34)c3ccccc32)cc1.O=C(O)C=CC(=O)O
Storage condition 2-8°C

 Safety Information

RIDADR NONH for all modes of transport

 Synonyms

1'-{4-[1-(4-Fluorophenyl)-1H-indol-3-yl]butyl}-3H-spiro[2-benzofuran-1,4'-piperidine] (2E)-2-butenedioate (1:1)
Spiro[isobenzofuran-1(3H),4'-piperidine], 1'-[4-[1-(4-fluorophenyl)-1H-indol-3-yl]butyl]-, (2E)-2-butenedioate (1:1)
MFCD28016590
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