LANICEMINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H14N2
Molecular Weight	198.2637
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@@H](CC1=CC=CC=N1)C2=CC=CC=C2

InChI

InChIKey=FWUQWDCOOWEXRY-ZDUSSCGKSA-N

InChI=1S/C13H14N2/c14-13(11-6-2-1-3-7-11)10-12-8-4-5-9-15-12/h1-9,13H,10,14H2/t13-/m0/s1

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23206319

Lanicemine is a low-trapping NMDA channel blocker, which was developed by Fisons Pharmaceuticals and later by AstraZeneca for the treatment of the major depressive disorder. The development was terminated in phase II as the drug did not meet the primary endpoint.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate [NMDA] receptor 125 Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23206319	Blocker 537		0.56 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Major depressive disorder 173 Sources: https://clinicaltrials.gov/ct2/show/NCT00781742	Primary		Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
1.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25259653/	150 mg single, intravenous dose: 150 mg route of administration: Intravenous experiment type: SINGLE co-administered:		LANICEMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
17.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25259653/	150 mg single, intravenous dose: 150 mg route of administration: Intravenous experiment type: SINGLE co-administered:		LANICEMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
16.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25259653/	150 mg single, intravenous dose: 150 mg route of administration: Intravenous experiment type: SINGLE co-administered:		LANICEMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00AD4Q	https://www.1pchem.com/search?query=1P00AD4Q
1PlusChem LLC	1P00EJZM	https://www.1pchem.com/search?query=1P00EJZM
A2B Chem	AG78290	http://a2bchem.com/prod/AG78290
AA Blocks	AA00EJG6	http://aablocks.com/goods/Goods/detail?id=AA00EJG6
ApexBio Technology	C3205	https://www.apexbt.com/catalogsearch/result/?q=C3205
AstaTech	F50577	http://astatechinc.com/CPSResult.php?CRNO=F50577
BLD Pharm	BD219983	http://www.bldpharm.com/search/Search.html?keyword=BD219983
Cayman Chemical	9002129	http://www.caymanchem.com/app/template/Product.vm/catalog/9002129
Chem Scene	CS-0027621	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0027621
ChemShuttle	ZB0597	https://www.chemshuttle.com/catalogsearch/result/?q=ZB0597
Enamine	BBV-222921	http://www.enaminestore.com/catalog/BBV-222921
Enamine	BBV-39979302	http://www.enaminestore.com/catalog/BBV-39979302
Enamine	EN300-123342	https://www.enaminestore.com/catalog/EN300-123342
Enamine	EN300-177531	https://www.enaminestore.com/catalog/EN300-177531
Enamine	EN300-296414	https://www.enaminestore.com/catalog/EN300-296414
KeyOrganics	AS-48526	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-48526
MedChem Express	HY-108235	https://www.medchemexpress.com/search.html?q=HY-108235&ft=&fa=&fp=
MolPort	MolPort-005-236-823	https://www.molport.com/shop/molecule-link/MolPort-005-236-823
MolPort	MolPort-030-004-688	https://www.molport.com/shop/molecule-link/MolPort-030-004-688
MuseChem	R024441	https://www.musechem.com/product/R024441.html
eMolecules	208096178	https://orderbb.emolecules.com/search/#?query=208096178
eMolecules	37479073	https://orderbb.emolecules.com/search/#?query=37479073
eMolecules	49432046	https://orderbb.emolecules.com/search/#?query=49432046
eMolecules	49432074	https://orderbb.emolecules.com/search/#?query=49432074
eNovation Chemicals	D638519	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D638519&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-1880303673	https://mcule.com/MCULE-1880303673/
mcule	MCULE-5948255547	https://mcule.com/MCULE-5948255547/
mcule	MCULE-9163260065	https://mcule.com/MCULE-9163260065/

PubMed

Title	Date	PubMed
A study of the mechanisms involved in the neurotoxic action of 3,4-methylenedioxymethamphetamine (MDMA, 'ecstasy') on dopamine neurones in mouse brain.	2001 Dec	11739248
Effect of low-affinity NMDA receptor antagonists on electrical activity in mouse cortical slices.	2002 May 17	12044795
Assessment of cognitive and motor deficits in a marmoset model of stroke.	2003	12652010
NXY-059: a hopeful sign in the treatment of stroke.	2006 Oct	16946156
Glutamate receptor-mediated inhibition of L-glutamate efflux from cerebral cortex in vitro.	2006 Oct 9	16904087

Patents

Sample Use Guides

In Vivo Use Guide

50-150 mg of the drug is given as a single intravenous (iv) infusion over 60 minutes.

Route of Administration: Intravenous

In Vitro Use Guide

Rat cortical neurons were exposed to NMDA (50 uM) or glutamate (50 uM) for 15 min, the treatment resulted in the death of 85-95% of the neurons during the next 24 h. Lanicemine inhibited the neurotoxicity at 50 uM, prevented the loss of membrane-associated protein kinase C activity and reduced by approximately 35% the magnitude of NMDA-triggered increases in intracellular free Ca2+ concentration in the cortical cultures.

Name

Type

Language

LANICEMINE

Official Name

English

lanicemine [INN]

Common Name

English

(+)-2-((S)-.BETA.-AMINOPHENETHYL)PYRIDINE

Systematic Name

English

AZD6765

Code

English

Lanicemine [WHO-DD]

Common Name

English

AZD-6765

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1509