CAS 147817-50-3|siramesine

Introduction：Basic information about CAS 147817-50-3|siramesine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. siramesine BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Synonyms

Common Name	siramesine
CAS Number	147817-50-3	Molecular Weight	454.578
Density	1.2±0.1 g/cm3	Boiling Point	611.4±55.0 °C at 760 mmHg
Molecular Formula	C₃₀H₃₁FN₂O	Melting Point	/
MSDS	/	Flash Point	323.6±31.5 °C

Names

Name	1'-[4-[1-(4-fluorophenyl)indol-3-yl]butyl]spiro[1H-2-benzofuran-3,4'-piperidine]
Synonym	More Synonyms

siramesine BiologicalActivity

Description	Siramesine(Lu 28-179) is a selective sigma-2 receptor agonist, which has been shown to trigger cell death of cancer cells and to exhibit a potent anticancer activity in vivo. IC50 value:Target: sigma-2 receptor; lysosome-destabilizing agentsiramesine can induce rapid cell death in a number of cell lines at concentrations above 20 μM. In HaCaT cells, cell death was accompanied by caspase activation, rapid loss of mitochondrial membrane potential (MMP), cytochrome c release, cardiolipin peroxidation and typical apoptotic morphology, whereas in U-87MG cells most apoptotic hallmarks were not notable, although MMP was rapidly lost [1]. Siramesine, a sigma-2 receptor agonist originally developed as an anti-depressant, can induce cell death in transformed cells through a mechanism involving lysosomal destabilization [2].in vivo: SA4503 or siramesine given jointly with MEM (as well as with AMA) decreased the immobility time in rats. The effect of SA4503 and AMA co-administration was antagonized by progesterone, a sigma1 receptor antagonistic neurosteroid. Combined treatment with siramesine and AMA was modified by neither progesterone nor BD1047 (a novel sigma antagonist with preferential affinity for sigma1 sites) [3]
Related Catalog	Signaling Pathways >>GPCR/G Protein >>Sigma ReceptorResearch Areas >>Cancer
References	[1]. Cesen MH, et al. Siramesine triggers cell death through destabilisation of mitochondria, but not lysosomes. Cell Death Dis. 2013 Oct 3;4:e818. [2]. Spirkoski J, et al. Mast cell apoptosis induced by siramesine, a sigma-2 receptor agonist. Biochem Pharmacol. 2012 Dec 15;84(12):1671-80. [3]. Skuza G, et al. The synergistic effect of selective sigma receptor agonists and uncompetitive NMDA receptor antagonists in the forced swim test in rats. J Physiol Pharmacol. 2006 Jun;57(2):217-29.

Description

Siramesine(Lu 28-179) is a selective sigma-2 receptor agonist, which has been shown to trigger cell death of cancer cells and to exhibit a potent anticancer activity in vivo. IC50 value:Target: sigma-2 receptor; lysosome-destabilizing agentsiramesine can induce rapid cell death in a number of cell lines at concentrations above 20 μM. In HaCaT cells, cell death was accompanied by caspase activation, rapid loss of mitochondrial membrane potential (MMP), cytochrome c release, cardiolipin peroxidation and typical apoptotic morphology, whereas in U-87MG cells most apoptotic hallmarks were not notable, although MMP was rapidly lost [1]. Siramesine, a sigma-2 receptor agonist originally developed as an anti-depressant, can induce cell death in transformed cells through a mechanism involving lysosomal destabilization [2].in vivo: SA4503 or siramesine given jointly with MEM (as well as with AMA) decreased the immobility time in rats. The effect of SA4503 and AMA co-administration was antagonized by progesterone, a sigma1 receptor antagonistic neurosteroid. Combined treatment with siramesine and AMA was modified by neither progesterone nor BD1047 (a novel sigma antagonist with preferential affinity for sigma1 sites) [3]

Related Catalog

Signaling Pathways >>GPCR/G Protein >>Sigma ReceptorResearch Areas >>Cancer

References

[1]. Cesen MH, et al. Siramesine triggers cell death through destabilisation of mitochondria, but not lysosomes. Cell Death Dis. 2013 Oct 3;4:e818.

[2]. Spirkoski J, et al. Mast cell apoptosis induced by siramesine, a sigma-2 receptor agonist. Biochem Pharmacol. 2012 Dec 15;84(12):1671-80.

[3]. Skuza G, et al. The synergistic effect of selective sigma receptor agonists and uncompetitive NMDA receptor antagonists in the forced swim test in rats. J Physiol Pharmacol. 2006 Jun;57(2):217-29.

Chemical & Physical Properties

Density	1.2±0.1 g/cm3
Boiling Point	611.4±55.0 °C at 760 mmHg
Molecular Formula	C₃₀H₃₁FN₂O
Molecular Weight	454.578
Flash Point	323.6±31.5 °C
Exact Mass	454.242035
PSA	17.40000
LogP	9.19
Vapour Pressure	0.0±1.8 mmHg at 25°C
Index of Refraction	1.629
InChIKey	XWAONOGAGZNUSF-UHFFFAOYSA-N
SMILES	Fc1ccc(-n2cc(CCCCN3CCC4(CC3)OCc3ccccc34)c3ccccc32)cc1
Storage condition	-20℃

Safety Information

Hazard Codes	Xi

Synonyms

QCR-66

UNII-3IX8CWR24V

1'-{4-[1-(4-Fluorophenyl)-1H-indol-3-yl]butyl}-3H-spiro[2-benzofuran-1,4'-piperidine]

siramesine

Lu 28-179

Spiro[isobenzofuran-1(3H),4'-piperidine], 1'-[4-[1-(4-fluorophenyl)-1H-indol-3-yl]butyl]-

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