NEBOGLAMINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H24N2O3
Molecular Weight	256.3413
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)CCC(CC1)NC(=O)[C@@H](N)CCC(O)=O

InChI

InChIKey=VCRGLZYPNNAVRP-JTQLQIEISA-N

InChI=1S/C13H24N2O3/c1-13(2)7-5-9(6-8-13)15-12(18)10(14)3-4-11(16)17/h9-10H,3-8,14H2,1-2H3,(H,15,18)(H,16,17)/t10-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9004193
Curator's Comment: description was created based on several sources, including: http://www.rotta.com/en/service/media/comunicatiStampa/pdf/2._Neboglamine_-_January_2005.pdf | https://www.ncbi.nlm.nih.gov/pubmed/25234340

Neboglamine is a functional modulator of the glycine site on the N-methyl-D-aspartate (NMDA) receptor. Neboglamine appeared to promote neuronal growth as measured by expression of Fos-like immunoreactivity, particularly in the prefrontal cortex, nucleus accumbens, and lateral septal nucleus. Neboglamine behaves as a potential antipsychotic. Neboglamine is in phase II clinical trials by Rottapharm for the treatment of schizophrenia and cocaine abuse.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate [NMDA] receptor 125 Target ID: CHEMBL2094124 Sources: http://fens2010.neurosciences.asso.fr/abstracts/rpdf3/a079_21.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/25234340	Positive Allosteric Modulator 179		10.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25234340 https://www.ncbi.nlm.nih.gov/pubmed/20045056 http://fens2010.neurosciences.asso.fr/abstracts/rpdf3/a079_21.pdf	Primary		Phase II 1132	Unknown Approved Use Unknown
Cocaine addiction 28 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25234340 https://www.google.ch/patents/US8258185	Primary		Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
Alfa Chemistry	163000-63-3	http://www.alfa-chemistry.com/search.aspx?q=163000-63-3
Alfa Chemistry	ACM163000633	http://www.alfa-chemistry.com/search.aspx?q=ACM163000633
BOC Sciences	163000-63-3
Enamine	BBV-39454464	http://www.enaminestore.com/catalog/BBV-39454464
MolPort	MolPort-021-680-724	https://www.molport.com/shop/molecule-link/MolPort-021-680-724
MuseChem	M137560	https://www.musechem.com/product/M137560.html
Tetrahedron	TS67891	http://www.thsci.com/search.do?q=TS67891

PubMed

Title	Date	PubMed
Characterization of a novel putative cognition enhancer mediating facilitation of glycine effect on strychnine-resistant sites coupled to NMDA receptor complex.	1997 Aug	9294970
The "kynurenate test", a biochemical assay for putative cognition enhancers.	1997 Oct	9336311
Antipsychotic-like effects of the N-methyl-D-aspartate receptor modulator neboglamine: an immunohistochemical and behavioural study in the rat.	2010 May	20045056

Patents

Sample Use Guides

In Vivo Use Guide

Single dose 200 mg

Route of Administration: Oral

In Vitro Use Guide

Neboglamine bounds very weakly to the recognition site of NMDA receptor (IC50 0.7 mM) and had no significant binding affinity to the two other subtypes, i.e. AMPA (DL-[3H]a-amino-3- hydroxy-5-methylisoxazole-4-propionic acid) and kainic receptors.

Name

Type

Language

NEBOGLAMINE

Official Name

English

XY-2401

Code

English

NEBOSTINEL

Common Name

English

(S)-4-AMINO-N-(4,4-DIMETHYLCYCLOHEXYL)GLUTARAMIC ACID

Systematic Name

English

neboglamine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1509