Welcome to Hodoodo Chemicals

Siramesine Fumarate
featured

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

Hodoodo CAT#: H529521

CAS#: 163630-79-3 (fumarate)

Description: Siramesine Fumarate is a sigma receptor agonist potentially for the treatment of generalized anxiety disorder

Chemical Structure

Siramesine Fumarate

CAS# 163630-79-3 (fumarate)

Instruction

Theoretical Analysis

Hodoodo Cat#: H529521
Name: Siramesine Fumarate
CAS#: 163630-79-3 (fumarate)
Chemical Formula: C34H35FN2O5
Exact Mass: 0.00
Molecular Weight: 570.661
Elemental Analysis: C, 71.56; H, 6.18; F, 3.33; N, 4.91; O, 14.02

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 275
25mg	USD 565
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. Hodoodo 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: LU-28-179; LU-28179; LU 28 179

IUPAC/Chemical Name: 1'-(4-(1-(4-fluorophenyl)-1H-indol-3-yl)butyl)-3H-spiro[isobenzofuran-1,4'-piperidine] fumarate

InChi Key: VONJQLKJOYOVBE-WLHGVMLRSA-N

InChi Code: InChI=1S/C30H31FN2O.C4H4O4/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;5-3(6)1-2-4(7)8/h1-4,8-15,21H,5-7,16-20,22H2;1-2H,(H,5,6)(H,7,8)/b;2-1+

SMILES Code: FC1=CC=C(N2C=C(CCCCN3CCC4(CC3)OCC5=C4C=CC=C5)C6=C2C=CC=C6)C=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

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

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 570.66 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:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.

Mass

Concentration

Volume

M. Wt* g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

Dilution Calculator

Calculate the dilution required to prepare a stock solution.

Concentration 1

Volume 1

Concentration 2

Volume 2

1: Česen MH, Repnik U, Turk V, Turk B. Siramesine triggers cell death through destabilisation of mitochondria, but not lysosomes. Cell Death Dis. 2013 Oct 3;4:e818. doi: 10.1038/cddis.2013.361. PubMed PMID: 24091661; PubMed Central PMCID: PMC3824671.

2: Spirkoski J, Melo FR, Grujic M, Calounova G, Lundequist A, Wernersson S, Pejler G. Mast cell apoptosis induced by siramesine, a sigma-2 receptor agonist. Biochem Pharmacol. 2012 Dec 15;84(12):1671-80. doi: 10.1016/j.bcp.2012.09.028. PubMed PMID: 23058984.

3: Ma S, Henson ES, Chen Y, Gibson SB. Ferroptosis is induced following siramesine and lapatinib treatment of breast cancer cells. Cell Death Dis. 2016 Jul 21;7:e2307. doi: 10.1038/cddis.2016.208. PubMed PMID: 27441659; PubMed Central PMCID: PMC4973350.

4: Ostenfeld MS, Høyer-Hansen M, Bastholm L, Fehrenbacher N, Olsen OD, Groth-Pedersen L, Puustinen P, Kirkegaard-Sørensen T, Nylandsted J, Farkas T, Jäättelä M. Anti-cancer agent siramesine is a lysosomotropic detergent that induces cytoprotective autophagosome accumulation. Autophagy. 2008 May;4(4):487-99. PubMed PMID: 18305408.

5: Jonhede S, Petersen A, Zetterberg M, Karlsson JO. Acute effects of the sigma-2 receptor agonist siramesine on lysosomal and extra-lysosomal proteolytic systems in lens epithelial cells. Mol Vis. 2010 May 8;16:819-27. PubMed PMID: 20461150; PubMed Central PMCID: PMC2866574.

6: Hagforsen E, Lampinen M, Paivandy A, Weström S, Velin H, Öberg S, Pejler G, Rollman O. Siramesine causes preferential apoptosis of mast cells in skin biopsies from psoriatic lesions. Br J Dermatol. 2017 Jan 24. doi: 10.1111/bjd.15336. [Epub ahead of print] PubMed PMID: 28117878.

7: Ostenfeld MS, Fehrenbacher N, Høyer-Hansen M, Thomsen C, Farkas T, Jäättelä M. Effective tumor cell death by sigma-2 receptor ligand siramesine involves lysosomal leakage and oxidative stress. Cancer Res. 2005 Oct 1;65(19):8975-83. PubMed PMID: 16204071.

8: Zimmermann A, Tian F, Lopez de Diego H, Ringkjøbing Elema M, Rantanen J, Müllertz A, Hovgaard L. Influence of the solid form of siramesine hydrochloride on its behavior in aqueous environments. Pharm Res. 2009 Apr;26(4):846-54. doi: 10.1007/s11095-008-9783-0. PubMed PMID: 19005740.

9: Parry MJ, Alakoskela JM, Khandelia H, Kumar SA, Jäättelä M, Mahalka AK, Kinnunen PK. High-affinity small molecule-phospholipid complex formation: binding of siramesine to phosphatidic acid. J Am Chem Soc. 2008 Oct 1;130(39):12953-60. doi: 10.1021/ja800516w. PubMed PMID: 18767848.

10: Zimmermann A, Tian F, de Diego HL, Frydenvang K, Rantanen J, Elema MR, Hovgaard L. Structural characterisation and dehydration behaviour of siramesine hydrochloride. J Pharm Sci. 2009 Oct;98(10):3596-607. doi: 10.1002/jps.21679. PubMed PMID: 19156865.

11: Groth-Pedersen L, Ostenfeld MS, Høyer-Hansen M, Nylandsted J, Jäättelä M. Vincristine induces dramatic lysosomal changes and sensitizes cancer cells to lysosome-destabilizing siramesine. Cancer Res. 2007 Mar 1;67(5):2217-25. PubMed PMID: 17332352.

12: Søby KK, Mikkelsen JD, Meier E, Thomsen C. Lu 28-179 labels a sigma(2)-site in rat and human brain. Neuropharmacology. 2002 Jul;43(1):95-100. PubMed PMID: 12213263.

13: Zimmermann A, Millqvist-Fureby A, Elema MR, Hansen T, Müllertz A, Hovgaard L. Adsorption of pharmaceutical excipients onto microcrystals of siramesine hydrochloride: effects on physicochemical properties. Eur J Pharm Biopharm. 2009 Jan;71(1):109-16. doi: 10.1016/j.ejpb.2008.06.014. PubMed PMID: 18619536.

14: Nielsen AB, Buur A, Larsen C. Bioreversible quaternary N-acyloxymethyl derivatives of the poorly soluble tertiary amine Lu 28-179--synthesis, pharmaceutical chemical characterization and bioavailability studies in dogs. Eur J Pharm Sci. 2005 Dec;26(5):421-8. PubMed PMID: 16150581.

15: Sánchez C, Papp M. The selective sigma2 ligand Lu 28-179 has an antidepressant-like profile in the rat chronic mild stress model of depression. Behav Pharmacol. 2000 Apr;11(2):117-24. PubMed PMID: 10877116.

16: Heading C. Siramesine H Lundbeck. Curr Opin Investig Drugs. 2001 Feb;2(2):266-70. Review. PubMed PMID: 11816842.

17: Sánchez C, Arnt J, Costall B, Kelly ME, Meier E, Naylor RJ, Perregaard J. The selective sigma2-ligand Lu 28-179 has potent anxiolytic-like effects in rodents. J Pharmacol Exp Ther. 1997 Dec;283(3):1323-32. Erratum in: J Pharmacol Exp Ther 1998 May;285(2):929. PubMed PMID: 9400007.

18: Hagforsen E, Paivandy A, Lampinen M, Weström S, Calounova G, Melo FR, Rollman O, Pejler G. Ablation of human skin mast cells in situ by lysosomotropic agents. Exp Dermatol. 2015 Jul;24(7):516-21. doi: 10.1111/exd.12699. PubMed PMID: 25808581.

19: Petersen NH, Olsen OD, Groth-Pedersen L, Ellegaard AM, Bilgin M, Redmer S, Ostenfeld MS, Ulanet D, Dovmark TH, Lønborg A, Vindeløv SD, Hanahan D, Arenz C, Ejsing CS, Kirkegaard T, Rohde M, Nylandsted J, Jäättelä M. Transformation-associated changes in sphingolipid metabolism sensitize cells to lysosomal cell death induced by inhibitors of acid sphingomyelinase. Cancer Cell. 2013 Sep 9;24(3):379-93. doi: 10.1016/j.ccr.2013.08.003. PubMed PMID: 24029234.

20: Skuza G, Rogóz Z. 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. PubMed PMID: 16845227.

Your view history

Siramesine Fumarate featured