SELTOREXANT

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H22FN7O
Molecular Weight	407.4441
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CN(C[C@]1([H])CN(C2)C3=NC(C)=CC(C)=N3)C(=O)C4=C(C=CC=C4F)N5N=CC=N5

InChI

InChIKey=SQOCEMCKYDVLMM-IYBDPMFKSA-N

InChI=1S/C21H22FN7O/c1-13-8-14(2)26-21(25-13)28-11-15-9-27(10-16(15)12-28)20(30)19-17(22)4-3-5-18(19)29-23-6-7-24-29/h3-8,15-16H,9-12H2,1-2H3/t15-,16+

HIDE SMILES / InChI

Molecular Formula	C21H22FN7O
Molecular Weight	407.4441
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/29848147 | https://www.ncbi.nlm.nih.gov/pubmed/30644312 | https://adisinsight.springer.com/drugs/800040115 | http://www.minervaneurosciences.com/innovation-pipeline/min-202/

2-(4,6-DIMETHYLPYRIMIDIN-2-YL)-5-((2-FLUORO-6-(2H-1,2,3-TRIAZOL-2-YL)PHENYL)CARBONYL)OCTAHYDROPYRROLO(3,4-C)PYRROLE (Seltorexant, MIN 202), a small molecule, selective orexin receptor type-2 antagonist, is being developed by Minerva Neurosciences and Janssen Research & Development for the treatment of insomnia and major depressive disorder. Seltorexant has shown high in vitro affinity (affinity pKi =8.0 and 6.1 for OX2R and OX1R respectively) for the human OX2R and approximates two logs selectivity ratio versus its affinity for the OX1R. Seltorexant demonstrated a dose-dependent normalization of sleep and a trend towards improvement of subjective depressive symptoms in antidepressant-treated MDD patients with residual insomnia. Additionally, seltorexant’s favorable PK profile as a potential sedative-hypnotic drug was confirmed in a MDD population and did not demonstrate unacceptable adverse events or unwanted next-day CNS effects. Seltorexant is in phase II clinical trials for both insomnia and MDD.

CNS Activity

Originator

Approval Year

PubMed

Title	Date	PubMed
A randomized Phase 2 study to evaluate the orexin-2 receptor antagonist seltorexant in individuals with insomnia without psychiatric comorbidity.	2018 Jun	29848147
The selective orexin-2 receptor antagonist seltorexant improves sleep: An exploratory double-blind, placebo controlled, crossover study in antidepressant-treated major depressive disorder patients with persistent insomnia.	2019 Feb	30644312

Sample Use Guides

In Vivo Use Guide

Twenty male and female patients received a single dose of 10, 20, 40 mg seltorexant and placebo with a washout period of seven days in a double-blind four-way crossover study.

Route of Administration: Oral

In Vitro Use Guide

Seltorexant has shown high in vitro affinity (affinity pKi =8.0 and 6.1 for OX2R and OX1R respectively) for the human OX2R and approximates two logs selectivity ratio versus its affinity for the OX1R.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:25:17 UTC 2023` Edited by `admin` on `Sat Dec 16 08:25:17 UTC 2023`
Record UNII	AIS8N3O50B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SELTOREXANT

Official Name

English

JNJ-42847922

Code

English

(5-(4,6-DIMETHYL-2-PYRIMIDINYL)HEXAHYDROPYRROLO(3,4-C)PYRROL-2(1H)-YL)(2-FLUORO-6-(2H-1,2,3-TRIAZOL-2-YL)PHENYL)METHANONE

Systematic Name

English

((3AR,6AS)-5-(4,6-DIMETHYLPYRIMIDIN- 2-YL)HEXAHYDROPYRROLO(3,4-C)PYRROL-2(1H)-YL)(2-FLUORO- 6-(2H-1,2,3-TRIAZOL-2-YL)PHENYL)METHANONE OREXIN RECEPTOR ANTAGONIST

Common Name

English

Seltorexant [WHO-DD]

Common Name

English

METHANONE, ((3AR,6AS)-5-(4,6-DIMETHYL-2-PYRIMIDINYL)HEXAHYDROPYRROLO(3,4-C)PYRROL-2(1H)-YL)(2-FLUORO-6-(2H-1,2,3-TRIAZOL-2-YL)PHENYL)-, REL-

Common Name

English

SELTOREXANT [USAN]

Common Name

English

2-(4,6-DIMETHYLPYRIMIDIN-2-YL)-5-((2-FLUORO-6-(2H-1,2,3-TRIAZOL-2-YL)PHENYL)CARBONYL)OCTAHYDROPYRROLO(3,4-C)PYRROLE

Systematic Name

English

MIN-202

Code

English

METHANONE, (5-(4,6-DIMETHYL-2-PYRIMIDINYL)HEXAHYDROPYRROLO(3,4-C)PYRROL-2(1H)-YL)(2-FLUORO-6-(2H-1,2,3-TRIAZOL-2-YL)PHENYL)-

Systematic Name

English

seltorexant [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C265