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

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H20F2N4O2
Molecular Weight 410.4166
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEMBOREXANT

SMILES

CC1=NC=C(OC[C@]2(C[C@H]2C(=O)NC3=NC=C(F)C=C3)C4=CC=CC(F)=C4)C(C)=N1

InChI

InChIKey=MUGXRYIUWFITCP-PGRDOPGGSA-N
InChI=1S/C22H20F2N4O2/c1-13-19(11-25-14(2)27-13)30-12-22(15-4-3-5-16(23)8-15)9-18(22)21(29)28-20-7-6-17(24)10-26-20/h3-8,10-11,18H,9,12H2,1-2H3,(H,26,28,29)/t18-,22+/m0/s1

HIDE SMILES / InChI

Description

Lemborexant is a dual orexin receptor antagonist, which inhibits orexin by binding competitively to two subtypes of orexin receptors. During normal periods of sleep, orexin system activity is suppressed, suggesting it is possible to purposefully facilitate the initiation and maintenance of sleep by interfering with orexin neurotransmission with lemborexant. Extensive in vitro and non-clinical testing of lemborexant supported the supposition that lemborexant has a low risk of QT prolongation at therapeutic and supratherapeutic exposures in humans. A Phase III study of lemborexant in insomnia is underway, and in addition, Eisai has announced the initiation of Phase II clinical studies of lemborexant in patients with irregular sleep-wake rhythm disorder.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
6.1 µM [IC50]
2.6 nM [IC50]
6.1 nM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
In Vitro and In Silico Characterization of Lemborexant (E2006), a Novel Dual Orexin Receptor Antagonist.
2017 Aug
Concentration-Response Modeling of ECG Data From Early-Phase Clinical Studies as an Alternative Clinical and Regulatory Approach to Assessing QT Risk - Experience From the Development Program of Lemborexant.
2017 Jan
Patents

Patents

Sample Use Guides

In Vivo Use Guide
5 mg or 10 mg before the time the participant intends to try to sleep
Route of Administration: Oral
In Vitro Use Guide
The effect of lemborexant on the slow component of delayed rectifier potassium current (IKs) was examined using KCNQ1/KCNE1-CHO cells and a small, not-concentration-dependent inhibition was noted with a peak inhibitory effect of 24% at 10 (uM, and a smaller effect (13%) at 30 uM.
Name Type Language
LEMBOREXANT
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
(1R,2S)-2-(((2,4-DIMETHYLPYRIMIDIN-5-YL)OXY)METHYL)-2-(3-FLUOROPHENYL)-N-(5-FLUOROPYRIDIN-2-YL)CYCLOPROPANECARBOXAMIDE
Systematic Name English
CYCLOPROPANECARBOXAMIDE, 2-(((2,4-DIMETHYL-5-PYRIMIDINYL)OXY)METHYL)-2-(3-FLUOROPHENYL)-N-(5-FLUORO-2-PYRIDINYL)-, (1R,2S)-
Systematic Name English
E2006
Code English
LEMBOREXANT [INN]
Common Name English
E-2006
Code English
LEMBOREXANT [WHO-DD]
Common Name English
LEMBOREXANT [USAN]
Common Name English
Code System Code Type Description
INN
9988
Created by admin on Tue Oct 22 01:38:20 UTC 2019 , Edited by admin on Tue Oct 22 01:38:20 UTC 2019
PRIMARY
ChEMBL
CHEMBL3545367
Created by admin on Tue Oct 22 01:38:20 UTC 2019 , Edited by admin on Tue Oct 22 01:38:20 UTC 2019
PRIMARY
CAS
1369764-02-2
Created by admin on Tue Oct 22 01:38:20 UTC 2019 , Edited by admin on Tue Oct 22 01:38:20 UTC 2019
PRIMARY
WIKIPEDIA
Lemborexant
Created by admin on Tue Oct 22 01:38:20 UTC 2019 , Edited by admin on Tue Oct 22 01:38:20 UTC 2019
PRIMARY
PUBCHEM
56944144
Created by admin on Tue Oct 22 01:38:20 UTC 2019 , Edited by admin on Tue Oct 22 01:38:20 UTC 2019
PRIMARY