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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 of LANICEMINE

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

HIDE SMILES / InChI

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
Tolerability of the low-affinity, use-dependent NMDA antagonist AR-R15896AR in stroke patients: a dose-ranging study.
2001 Feb
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
NXY-059: a hopeful sign in the treatment of stroke.
2006 Oct
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 Sat Dec 16 17:02:37 UTC 2023
Edited
by admin
on Sat Dec 16 17:02:37 UTC 2023
Record UNII
9TMU325RK3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LANICEMINE
INN   WHO-DD  
INN  
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
Created by admin on Sat Dec 16 17:02:37 UTC 2023 , Edited by admin on Sat Dec 16 17:02:37 UTC 2023
Code System Code Type Description
FDA UNII
9TMU325RK3
Created by admin on Sat Dec 16 17:02:37 UTC 2023 , Edited by admin on Sat Dec 16 17:02:37 UTC 2023
PRIMARY
INN
7943
Created by admin on Sat Dec 16 17:02:37 UTC 2023 , Edited by admin on Sat Dec 16 17:02:37 UTC 2023
PRIMARY
PUBCHEM
9794203
Created by admin on Sat Dec 16 17:02:37 UTC 2023 , Edited by admin on Sat Dec 16 17:02:37 UTC 2023
PRIMARY
WIKIPEDIA
Lanicemine
Created by admin on Sat Dec 16 17:02:37 UTC 2023 , Edited by admin on Sat Dec 16 17:02:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID30870011
Created by admin on Sat Dec 16 17:02:37 UTC 2023 , Edited by admin on Sat Dec 16 17:02:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL2107647
Created by admin on Sat Dec 16 17:02:37 UTC 2023 , Edited by admin on Sat Dec 16 17:02:37 UTC 2023
PRIMARY
NCI_THESAURUS
C77601
Created by admin on Sat Dec 16 17:02:37 UTC 2023 , Edited by admin on Sat Dec 16 17:02:37 UTC 2023
PRIMARY
SMS_ID
100000174979
Created by admin on Sat Dec 16 17:02:37 UTC 2023 , Edited by admin on Sat Dec 16 17:02:37 UTC 2023
PRIMARY
CAS
153322-05-5
Created by admin on Sat Dec 16 17:02:37 UTC 2023 , Edited by admin on Sat Dec 16 17:02:37 UTC 2023
PRIMARY
DRUG BANK
DB11889
Created by admin on Sat Dec 16 17:02:37 UTC 2023 , Edited by admin on Sat Dec 16 17:02:37 UTC 2023
PRIMARY
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SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
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