| Identification | Back Directory | [Name]
SIRAMESINE | [CAS]
147817-50-3 | [Synonyms]
CS-1476
SIRAMESINE
1'-[4-[1-(4-fluorophenyl)indol-3-yl]butyl]spiro[1H-2-benzofuran-3,4'-piperidine]
1'-(4-(1-(4-fluorophenyl)-1H-indol-3-yl)butyl)-3H-spiro[isobenzofuran-1,4'-piperidine]
Spiro[isobenzofuran-1(3H),4'-piperidine], 1'-[4-[1-(4-fluorophenyl)-1H-indol-3-yl]butyl]-
1'-[4-[1-(4-Fluorophenyl)-1H-indol-3-yl]-1-butyl]spiro[isobenzofuran-1(3H),4'-piperidine]
1'-(4-(1-(4-FLUOROPHENYL)-1H-INDOL-3-YL)BUTYL)-3H-SPIRO[ISOBENZOFURAN-1,4'-PIPERIDINE].HCL | [Molecular Formula]
C30H31FN2O | [MDL Number]
MFCD00912182 | [MOL File]
147817-50-3.mol | [Molecular Weight]
454.58 |
| Chemical Properties | Back Directory | [Boiling point ]
611.4±55.0 °C(Predicted) | [density ]
1.19±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Soluble in DMSO (up to at least 25 mg/ml) | [form ]
solid | [pka]
9.45±0.20(Predicted) | [color ]
White | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. | [InChI]
InChI=1S/C30H31FN2O/c31-25-12-14-26(15-13-25)33-21-23(27-9-2-4-11-29(27)33)7-5-6-18-32-19-16-30(17-20-32)28-10-3-1-8-24(28)22-34-30/h1-4,8-15,21H,5-7,16-20,22H2 | [InChIKey]
XWAONOGAGZNUSF-UHFFFAOYSA-N | [SMILES]
C12(CCN(CCCCC3C4=C(N(C5=CC=C(F)C=C5)C=3)C=CC=C4)CC1)C1=C(C=CC=C1)CO2 |
| Hazard Information | Back Directory | [Description]
Siramesine (Lu 28-179, 147817-50-3) is a σ2 selective agonist?(IC50’s: σ1 = 17nM, σ2 = 0.2nM).1?It produced non-sedating potent and long-last anxiolytic effects in rodents.2?Siramesine induced caspase-independent programmed cell death in various cancer cell lines?via?increased levels of ROS and lysosomal leakage.3,4,5?Mitochondrial destabilization via loss of membrane potential and increased ROS has also been offered as a mechanism of action for the triggering of cell death by Siramesine.6 | [Uses]
Treatment of
prostate cancer. | [Brand name]
Provenge (Dendreon). | [IC 50]
Sigma 1 Receptor | [References]
1) Perregaard?et al.?(1995),?Sigma ligands with subnanomolar affinity and preference for the sigma 2 binding site. 1. 3-(omega-aminoalkyl)-1H-indoles; J. Med. Chem.?38?1998
2) Sanchez?et al.?(1997),?The selective sigma2-ligand Lu 280179 has potent anxiolytic effects in rodents; J. Pharmacol. Exp. Ther.?283?1323
3) Ostenfeld?et al.?(2005),?Effective tumor cell death by sigma-2 receptor ligand siramesine involves lysosomal leakage and oxidative stress;?Cancer Res.?65?8975
4) Ostenfeld et al. (2008),?Anti-cancer agent siramesine is a lysosomotropic detergent that induces cytoprotective autophagosome accumulation; Autophagy?4?487
5) Dielschneider?et al.?(2016),?Lysosomotropic agents selectively target chronic lymphocytic leukemia cells due to altered sphingolipid metabolism; Leukemia?30?1290
6) Cesen?et al.?(2013),?Siramesine triggers cell death through destabilization of mitochondria, but not lysosomes; Cell Death Dis.?4?e818 |
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