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Details

Stereochemistry RACEMIC
Molecular Formula C19H23FN4O2
Molecular Weight 358.4099
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RISLENEMDAZ, (±)-

SMILES

CC1=CC=C(COC(=O)N2CC[C@H](CNC3=NC=CC=N3)[C@H](F)C2)C=C1

InChI

InChIKey=RECBFDWSXWAXHY-IAGOWNOFSA-N
InChI=1S/C19H23FN4O2/c1-14-3-5-15(6-4-14)13-26-19(25)24-10-7-16(17(20)12-24)11-23-18-21-8-2-9-22-18/h2-6,8-9,16-17H,7,10-13H2,1H3,(H,21,22,23)/t16-,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula C19H23FN4O2
Molecular Weight 358.4099
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Rislenemdaz, also known as MK-0657 or CERC‐30, is an orally active, selective NMDA receptor subunit 2B (NR2B) antagonist which was a study for the treatment of Parkinson's disease and major depressive disorder (MDD). The data from the phase I clinical trials have shown that drug was not effective in improving motor symptoms in patients with Parkinson disease. In case of using this drug to treat MDD, in spite of the Missing Primary Endpoint in phase II clinical trials, it was shown, that MK-0657 had possessed a potential clinical meaningfulness, that is why it was suggested to continue studying it for MDD patients.

Originator

Curator's Comment: # Merck & Co, Inc

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q13224
Gene ID: 2904.0
Gene Symbol: GRIN2B
Target Organism: Homo sapiens (Human)
8.1 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
408 nM
7 mg single, oral
dose: 7 mg
route of administration: Oral
experiment type: SINGLE
co-administered: LEVODOPA
CERC-301 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
PubMed

PubMed

TitleDatePubMed
Single-dose administration of MK-0657, an NR2B-selective NMDA antagonist, does not result in clinically meaningful improvement in motor function in patients with moderate Parkinson's disease.
2009 Jul
A Randomized, placebo-controlled, crossover pilot trial of the oral selective NR2B antagonist MK-0657 in patients with treatment-resistant major depressive disorder.
2012 Aug
Preclinical pharmacology and pharmacokinetics of CERC-301, a GluN2B-selective N-methyl-D-aspartate receptor antagonist.
2015 Dec
A Phase Ib Randomized Controlled Study to Evaluate the Effectiveness of a Single-Dose of the NR2B Selective N-Methyl-D-Aspartate Antagonist MK-0657 on Levodopa-Induced Dyskinesias and Motor Symptoms in Patients With Parkinson Disease.
2017 Nov/Dec
Patents

Patents

Sample Use Guides

two dose (20 mg) administrations 7 days apart (Day 0 and Day 7) followed by 14 days of observation for a total of 21 days.
Route of Administration: Oral
It was measured the functional activity and selectivity of CERC‐301 (MK-0657) for NMDA receptors. CERC‐301 inhibited calcium influx into agonist‐stimulated NMDA‐GluN1a/GluN2B L(tk‐) cells with an IC50 of 3.6 nmol L−1 but had no effect on calcium influx into agonist‐stimulated GluN1a/GluN2A cells at concentrations up to 30,000 nmol L−1 (30 μmol L−1). CERC‐301 exhibited no remarkable activity when tested in enzyme and radioligand binding assays at concentrations equal to and greater than 10 μmol L−1. CERC‐301 exhibited at least 1000 × selectivity for the GluN2B receptor versus all targets tested, including the hERG potassium channel. CERC‐301 also exhibited minimal activity against sigma‐type receptors at 10 μmol L−1 (sigma‐1, sigma‐2, and nonspecific).
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:56:36 GMT 2023
Edited
by admin
on Sat Dec 16 01:56:36 GMT 2023
Record UNII
1DY7M91WQ1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RISLENEMDAZ, (±)-
Common Name English
MK-0657, (±)-
Common Name English
1-PIPERIDINECARBOXYLIC ACID, 3-FLUORO-4-((2-PYRIMIDINYLAMINO)METHYL)-, (4-METHYLPHENYL)METHYL ESTER, (3R,4S)-REL-
Systematic Name English
CIS-4-METHYLBENZYL 3-FLUORO-4-((PYRIMIDIN-2-YLAMINO)METHYL)PIPERIDINE-1-CARBOXYLATE
Systematic Name English
Code System Code Type Description
PUBCHEM
11394238
Created by admin on Sat Dec 16 01:56:36 GMT 2023 , Edited by admin on Sat Dec 16 01:56:36 GMT 2023
PRIMARY
FDA UNII
1DY7M91WQ1
Created by admin on Sat Dec 16 01:56:36 GMT 2023 , Edited by admin on Sat Dec 16 01:56:36 GMT 2023
PRIMARY
WIKIPEDIA
MK 0657
Created by admin on Sat Dec 16 01:56:36 GMT 2023 , Edited by admin on Sat Dec 16 01:56:36 GMT 2023
PRIMARY
CAS
808733-05-3
Created by admin on Sat Dec 16 01:56:36 GMT 2023 , Edited by admin on Sat Dec 16 01:56:36 GMT 2023
PRIMARY
CAS
1221592-28-4
Created by admin on Sat Dec 16 01:56:36 GMT 2023 , Edited by admin on Sat Dec 16 01:56:36 GMT 2023
SUPERSEDED
Related Record Type Details
ACTIVE MOIETY