RISLENEMDAZ

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H23FN4O2
Molecular Weight	358.4099
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29059133 | https://www.streetinsider.com/Corporate News/Cerecor (CERC) Announces CERC-301 Phase 2 Missed Primary Endpoint in MDD/12292976.html

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate receptor ionotropic, NMDA 2B 5 Target ID: Q13224 Gene ID: 2904.0 Gene Symbol: GRIN2B Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19491335	Antagonist 2778		8.1 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Parkinson's disease 226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29059133	Primary		Phase I 428	Unknown Approved Use Unknown
Major depressive disorder 173 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26997505	Primary		Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
408 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29059133	7 mg single, oral dose: 7 mg route of administration: Oral experiment type: SINGLE co-administered: LEVODOPA	LEVODOPA	CERC-301 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P003AGJ	https://www.1pchem.com/search?query=1P003AGJ
AChemBlock	L22420	http://www.achemblock.com/catalogsearch/result/?q=L22420
AstaTech	41556	http://astatechinc.com/CPSResult.php?CRNO=41556
Chem Scene	CS-7798	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-7798
KeyOrganics	AS-35130	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-35130
MedChem Express	HY-106441A	https://www.medchemexpress.com/search.html?q=HY-106441A&ft=&fa=&fp=
MolPort	MolPort-046-416-865	https://www.molport.com/shop/molecule-link/MolPort-046-416-865
Molcore	MC445667	http://www.molcore.com/CatMC445667.html
Molnova	M16023	https://www.molnova.com/en/serch-list.html?keywords=M16023
MuseChem	I009047	https://www.musechem.com/product/I009047.html
eMolecules	271384898	https://orderbb.emolecules.com/search/#?query=271384898
eMolecules	89939687	https://orderbb.emolecules.com/search/#?query=89939687
eNovation Chemicals	D586481	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D586481&searchbtn.x=0&searchbtn.y=0

PubMed

Title	Date	PubMed
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	19491335
Preclinical pharmacology and pharmacokinetics of CERC-301, a GluN2B-selective N-methyl-D-aspartate receptor antagonist.	2015 Dec	27022470

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 17:26:06 UTC 2023` Edited by `admin` on `Sat Dec 16 17:26:06 UTC 2023`
Record UNII	5HAM167S5T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RISLENEMDAZ

Official Name

English

4-METHYLBENZYL (3S,4R)-3-FLUORO-4-((PYRIMIDIN-2-YLAMINO)METHYL)PIPERIDINE-1-CARBOXYLATE

Systematic Name

English

Rislenemdaz [WHO-DD]

Common Name

English

CERC-301

Code

English

(-)-(3S,4R)-4-METHYLBENZYL 3-FLUORO-4-((PYRIMIDIN-2-YLAMINO)METHYL)PIPERIDINE-1-CARBOXYLATE

Systematic Name

English

RISLENEMDAZ [USAN]

Common Name

English

MK-0657, (-)-

Code

English

RISLENEMDAZ, (-)-

Common Name

English

rislenemdaz [INN]

Common Name

English

(-)-(3S,4R)-4-METHYLBENZYL-3-FLOURO-4-((PYRIMIDIN-2-YLAMINO)METHYL)PIPERIDINE-1-CARBOXYLATE

Systematic Name

English

MK-0657

Code

English

1-PIPERIDINECARBOXYLIC ACID, 3-FLUORO-4-((2-PYRIMIDINYLAMINO)METHYL)-, (4-METHYLPHENYL)METHYL ESTER, (3S,4R)-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C265