U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C13H14N2.2ClH
Molecular Weight 271.186
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LANICEMINE DIHYDROCHLORIDE

SMILES

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

InChI

InChIKey=KHJHFYAGQZYCLC-GXKRWWSZSA-N
InChI=1S/C13H14N2.2ClH/c14-13(11-6-2-1-3-7-11)10-12-8-4-5-9-15-12;;/h1-9,13H,10,14H2;2*1H/t13-;;/m0../s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C13H14N2
Molecular Weight 198.2637
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.56 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.3 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
17.9 μg × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
16.1 h
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

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
A study of the mechanisms involved in the neurotoxic action of 3,4-methylenedioxymethamphetamine (MDMA, 'ecstasy') on dopamine neurones in mouse brain.
2001 Dec
Tolerability of the low-affinity, use-dependent NMDA antagonist AR-R15896AR in stroke patients: a dose-ranging study.
2001 Feb
On the relationship between plasma concentrations of drugs and outcome of stroke studies in laboratory animals.
2001 Jun
Structural modifications to an N-methyl-D-aspartate receptor antagonist result in large differences in trapping block.
2001 Jun
Differential effects of remacemide and desglycinyl-remacemide on epileptiform burst firing in the rat hippocampal slice.
2002 Mar 15
Treatment of acute ischaemic stroke with the low-affinity, use-dependent NMDA antagonist AR-R15896AR. A safety and tolerability study.
2002 May
Effect of low-affinity NMDA receptor antagonists on electrical activity in mouse cortical slices.
2002 May 17
Assessment of cognitive and motor deficits in a marmoset model of stroke.
2003
Comparison of the neuroprotective effect of clomethiazole, AR-R15896AR and NXY-059 in a primate model of stroke using histological and behavioural measures.
2003 May 16
NXY-059: a hopeful sign in the treatment of stroke.
2006 Oct
Glutamate receptor-mediated inhibition of L-glutamate efflux from cerebral cortex in vitro.
2006 Oct 9
Patents

Patents

Sample Use Guides

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:28:54 GMT 2023
Edited
by admin
on Fri Dec 15 16:28:54 GMT 2023
Record UNII
59E712CNQR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LANICEMINE DIHYDROCHLORIDE
Common Name English
ARL-15896AR
Code English
(1S)-1-PHENYL-2-PYRIDIN-2-YLETHANAMINE DIHYDROCHLORIDE
Systematic Name English
FPL-15896AR
Code English
AZD-6765 DIHYDROCHLORIDE
Code English
2-PYRIDINEETHANAMINE, .ALPHA.-PHENYL-, (.ALPHA.S)-, DIHYDROCHLORIDE
Common Name English
Code System Code Type Description
CAS
153322-06-6
Created by admin on Fri Dec 15 16:28:54 GMT 2023 , Edited by admin on Fri Dec 15 16:28:54 GMT 2023
PRIMARY
FDA UNII
59E712CNQR
Created by admin on Fri Dec 15 16:28:54 GMT 2023 , Edited by admin on Fri Dec 15 16:28:54 GMT 2023
PRIMARY
PUBCHEM
9795446
Created by admin on Fri Dec 15 16:28:54 GMT 2023 , Edited by admin on Fri Dec 15 16:28:54 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY