CUTAMESINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H32N2O2
Molecular Weight	368.5124
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(CCN2CCN(CCCC3=CC=CC=C3)CC2)C=C1OC

InChI

InChIKey=UVSWWUWQVAQPJR-UHFFFAOYSA-N

InChI=1S/C23H32N2O2/c1-26-22-11-10-21(19-23(22)27-2)12-14-25-17-15-24(16-18-25)13-6-9-20-7-4-3-5-8-20/h3-5,7-8,10-11,19H,6,9,12-18H2,1-2H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25270629 | https://www.ncbi.nlm.nih.gov/pubmed/8813641

Cutamesine, an agonsit of brain sigma 1 receptors, was developed by Santen Pharmaceutical for the treatment of cognitive diseases. The drug was tested in phase II in patients with major depressive disorders and for recovery of patients with stroke, however its development was terminated for the given conditions. Currently M's science corporation is developing cutamesine for Amyotrophic lateral sclerosis and Retinitis pigmentosa as more suitable target diseases.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sigma opioid receptor 63 Target ID: CHEMBL287 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8813641 \| http://www.m-sci.com/e/pipeline/cutamesine.html	Agonist 2678		17.4 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Major depressive disorder 173 Sources: https://clinicaltrials.gov/ct2/show/NCT00551109	Primary	Phase II 1132	Unknown Approved Use Unknown
Ischemic stroke 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25270629	Palliative	Phase II 1132	Unknown Approved Use Unknown
Amyotrophic lateral sclerosis 41 Sources: https://web.archive.org/web/20170506065509/http://www.m-sci.com:80/e/pipeline/cutamesine.html	Primary	Phase I 428	Unknown Approved Use Unknown
Retinitis pigmentosa 10 Sources: https://web.archive.org/web/20170506065509/http://www.m-sci.com:80/e/pipeline/cutamesine.html	Primary	Phase I 428	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
3 mg 1 times / day multiple, oral Highest studied dose Dose: 3 mg, 1 times / day Route: oral Route: multiple Dose: 3 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25270629	unhealthy, ADULT n = 19 Health Status: unhealthy Condition: stroke Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 19 Sources: https://pubmed.ncbi.nlm.nih.gov/25270629	Sources: https://pubmed.ncbi.nlm.nih.gov/25270629

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P001WL0	https://www.1pchem.com/search?query=1P001WL0
ACT Chemical	ACT05974	http://www.actchemical.com/search.php?product=ACT05974
AChemBlock	M15302	http://www.achemblock.com/catalogsearch/result/?q=M15302
AK Scientific	8394AA	https://aksci.com/item_detail.php?cat=8394AA
AbovChem LLC	HY-14813	http://www.abovchem.com/pc/en/product_list.aspx?wd=HY-14813
Ambeed	A260566	http://www.ambeed.com/search/Search.html?keyword=A260566
AstaTech	88438	http://astatechinc.com/CPSResult.php?CRNO=88438
AstaTech	C73195	http://astatechinc.com/CPSResult.php?CRNO=C73195
Axon MedChem	1767	https://www.axonmedchem.com/product/1767
BLD Pharm	BD630420	http://www.bldpharm.com/search/Search.html?keyword=BD630420
BOC Sciences	165377-43-5	http://www.bocsci.com/description.asp?cas=165377-43-5
BOC Sciences	165377-44-6	http://www.bocsci.com/description.asp?cas=165377-44-6
Capot Chemical	31876	https://www.capotchem.com/search.do?q=31876
Chem Scene	CS-3288	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3288
ChemShuttle	156637	https://www.chemshuttle.com/catalogsearch/result/?q=156637
Combi-Blocks	QM-1454	http://www.combi-blocks.com/cgi-bin/find.cgi?QM-1454
Debye Scientific	DB-018483	https://www.debyesci.com/index.php?id=product&ext[cno]=DB-018483
Excenen	EX-A1190	http://www.excenen.com/searchresultlist.php?id=EX-A1190
Hairui	HR105207	http://www.hairuichem.com/en/product/search.do?q=HR105207
KeyOrganics	AS-43058	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-43058
Lab Network	LN01343278	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01343278
MedChem Express	HY-13510	https://www.medchemexpress.com/search.html?q=HY-13510&ft=&fa=&fp=
MolPort	MolPort-005-942-600	https://www.molport.com/shop/molecule-link/MolPort-005-942-600
MolPort	MolPort-009-198-795	https://www.molport.com/shop/molecule-link/MolPort-009-198-795
Molnova	M17359	https://www.molnova.com/en/serch-list.html?keywords=M17359
MuseChem	I006314	https://www.musechem.com/product/I006314.html
ShangHai Biochempartner	BCP19110	http://www.biochempartner.com/search_BCP19110
Sigma Aldrich	SML2181	http://www.sigmaaldrich.com/catalog/search?term=SML2181&interface=All&N=0&mode=match%20partialmax&lang=en®ion=US&focus=product
TargetMol	T3597	https://www.targetmol.com/search?keyword=T3597
Tocris	4951	https://www.tocris.com/search.php?Type=QuickSearch&Value=4951
Wonderchem	WD05CEK	http://www.wonder-chem.com/search.html?text=WD05CEK
eMolecules	300651292	https://orderbb.emolecules.com/search/#?query=300651292
eMolecules	42777426	https://orderbb.emolecules.com/search/#?query=42777426
eMolecules	50285353	https://orderbb.emolecules.com/search/#?query=50285353
eNovation Chemicals	D621218	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D621218&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-2101561668	https://mcule.com/MCULE-2101561668/
mcule	MCULE-7709952705	https://mcule.com/MCULE-7709952705/

PubMed

Title	Date	PubMed
Phencyclidine impairs latent learning in mice: interaction between glutamatergic systems and sigma(1) receptors.	2001 Apr	11182540
The selective sigma(1) receptor agonist, 1-(3,4-dimethoxyphenethyl)-4-(phenylpropyl)piperazine (SA4503), blocks the acquisition of the conditioned place preference response to (-)-nicotine in rats.	2001 Aug 24	11525784
Involvement of kappa-opioid and sigma receptors in short-term memory in mice.	2002 Oct 18	12393064
Synthesis and in vitro evaluation of iodinated derivatives of piperazine as a new ligand for sigma receptor imaging by single photon emission computed tomography.	2006 Apr	16595947
In vivo evaluation of radioiodinated 1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)-piperazine derivatives as new ligands for sigma receptor imaging using single photon emission computed tomography.	2006 Oct	17015942
Role of N-methyl-D-aspartate receptors in antidepressant-like effects of sigma 1 receptor agonist 1-(3,4-dimethoxyphenethyl)-4-(3-phenylpropyl)piperazine dihydrochloride (SA-4503) in olfactory bulbectomized rats.	2007 Sep	17556637
Pharmacology and therapeutic potential of sigma(1) receptor ligands.	2008 Dec	19587856
Sigma-1 receptor agonist fluvoxamine for delirium in intensive care units: report of five cases.	2010 Apr 24	20416097
Fluvoxamine for blonanserin-associated akathisia in patients with schizophrenia: report of five cases.	2010 Apr 24	20416096
Sigma-1 receptor agonist fluvoxamine for delirium in patients with Alzheimer's disease.	2010 Jan 20	20148109
Sigma-1 receptor agonist fluvoxamine for postoperative delirium in older adults: report of three cases.	2010 Jun 24	20573265
Fluvoxamine for aripiprazole-associated akathisia in patients with schizophrenia: a potential role of sigma-1 receptors.	2010 Mar 6	20205742

Patents

Sample Use Guides

In Vivo Use Guide

Patients with stroke receive cutamesine at a dose of 1 mg/day or 3 mg/day for 28 days.

Route of Administration: Oral

In Vitro Use Guide

Mice motor neuron cells were treated with cutamesine at concentration of 1-10 uM and the drug was shown to reduce SOD1(G93A)-induced cell death in a concentration-dependent manner.

Name

Type

Language

CUTAMESINE

Official Name

English

SA-4503

Common Name

English

1-(2-(3,4-DIMETHOXYPHENYL)ETHYL)-4-(3-PHENYLPROPYL)PIPERAZINE

Systematic Name

English

cutamesine [INN]

Common Name

English

Cutamesine [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C265