SELFOTEL, (-)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C7H14NO5P
Molecular Weight	223.1635
Optical Activity	( - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)[C@H]1C[C@@H](CP(O)(O)=O)CCN1

InChI

InChIKey=LPMRCCNDNGONCD-NTSWFWBYSA-N

InChI=1S/C7H14NO5P/c9-7(10)6-3-5(1-2-8-6)4-14(11,12)13/h5-6,8H,1-4H2,(H,9,10)(H2,11,12,13)/t5-,6+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C7H14NO5P
Molecular Weight	223.1635
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2899170
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/10657404

Selfotel is a competitive NMDA antagonist with (-)-enantiomer is more active than ( )-enantiomer. Selfotel was investigated in phase III clinical trials for ischemic stroke and severe head injury. Development of the drug was discontinued due to lack of efficacy and possible neurotoxicity discovered in clinical trials.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate NMDA receptor 46 Target ID: CHEMBL1907608 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2899170	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ischemic stroke 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10657404	Primary		Phase III 656	Unknown Approved Use Unknown
Head injury 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10541229	Primary		Phase III 656	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587 activator 80	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 1478 CYP1A2 1524

Drug as perpetrator

Target	Modality	Activity
CYP2C9 1819	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/883#sid=11113988	no
CYP2D6 1891	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/891#sid=11113988	no
CYP3A4 1925	activator 214 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/885#sid=11113988	no
CYP3A4 1925	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/884#sid=11113988	no
CYP1A2 1692	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/410#sid=11113988	yes [IC50 25.12 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/899#sid=11113988	yes [IC50 7.9433 uM]

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY34325	https://www.001chemical.com/chem/search?q=DY34325
Chemspace	CSC010464984	https://chem-space.com/CSC010464984
Chemspace	CSC015679529	https://chem-space.com/CSC015679529
Debye Scientific	DB-040917	https://www.debyesci.com/index.php?id=product&ext[cno]=DB-040917
Enamine	BBV-45270803	http://www.enaminestore.com/catalog/BBV-45270803
Enamine	BBV-83051701	http://www.enaminestore.com/catalog/BBV-83051701
Hairui	HR149764	http://www.hairuichem.com/en/product/search.do?q=HR149764
KeyOrganics	AS-71381	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-71381
Molcore	MC34325	http://www.molcore.com/CatMC34325.html
Molcore	MC439077	http://www.molcore.com/CatMC439077.html
MuseChem	M012261	https://www.musechem.com/product/M012261.html
Tocris	1241	https://www.tocris.com/search.php?Type=QuickSearch&Value=1241
Vesino Industrial Co Ltd	VP80203	http://www.vsnchem.com/search.do?a=s&psize=20&q=VP80203
eMolecules	1934116	https://orderbb.emolecules.com/search/#?query=1934116
mcule	MCULE-9483946552	https://mcule.com/MCULE-9483946552/

PubMed

Title	Date	PubMed
CGS 19755, a selective and competitive N-methyl-D-aspartate-type excitatory amino acid receptor antagonist.	1988 Jul	2899170

Patents

Sample Use Guides

In Vivo Use Guide

In a clinical trial against ischemic stroke, the compound was administered intravenously at 1-2 mg/kg.

Route of Administration: Intravenous

In Vitro Use Guide

Activity with respect to NMDA was measured by evaluating the inhibition of NMDA-evoked release of [3H]ACh from rat striatal slices. Slices were placed in superfusion chambers and superfused with a medium containing hemicholinium-3. NMDA (50uM) was added beginning at 57 min (SI) and 93 min (SII) after superfusion was started and kept in the medium for the duration of 2 min. The antagonist was added 18 min preceding SII and kept in the medium until the end of the experiment.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 07:59:47 GMT 2023` Edited by `admin` on `Sat Dec 16 07:59:47 GMT 2023`
Record UNII	EP2J4A2LB0
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

SELFOTEL, (-)-

Common Name

English

2-PIPERIDINECARBOXYLIC ACID, 4-(PHOSPHONOMETHYL)-, (2R,4S)-

Systematic Name

English

CGS-20281

Code

English

Code System Code Type Description

PUBCHEM

6604838

Created by admin on Sat Dec 16 07:59:47 GMT 2023 , Edited by admin on Sat Dec 16 07:59:47 GMT 2023

PRIMARY

CAS

113229-61-1

Created by admin on Sat Dec 16 07:59:47 GMT 2023 , Edited by admin on Sat Dec 16 07:59:47 GMT 2023

PRIMARY

FDA UNII

EP2J4A2LB0

Created by admin on Sat Dec 16 07:59:47 GMT 2023 , Edited by admin on Sat Dec 16 07:59:47 GMT 2023

PRIMARY

Related Record Type Details


					4VGJ4A41L2

SELFOTEL

RACEMATE -> ENANTIOMER

Amount:


					N0905W44Y3

SELFOTEL, (+)-

ENANTIOMER -> ENANTIOMER

Amount:

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/2899170Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/10657404

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Overview

OverviewOther

Drug as perpetrator​

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2899170
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/10657404

Drug as perpetrator