FILOREXANT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H25FN4O2
Molecular Weight	420.4793
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1CC[C@@H](COC2=CC=C(F)C=N2)CN1C(=O)C3=C(C=CC(C)=C3)C4=NC=CC=N4

InChI

InChIKey=NPFDWHQSDBWQLH-QZTJIDSGSA-N

InChI=1S/C24H25FN4O2/c1-16-4-8-20(23-26-10-3-11-27-23)21(12-16)24(30)29-14-18(6-5-17(29)2)15-31-22-9-7-19(25)13-28-22/h3-4,7-13,17-18H,5-6,14-15H2,1-2H3/t17-,18-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22019562
Curator's Comment: description was created based on several sources, including: http://adisinsight.springer.com/drugs/800031738 | https://en.wikipedia.org/wiki/Filorexant | https://www.ncbi.nlm.nih.gov/pubmed/26979830

Filorexant (MK-6096) is a novel, structurally distinct dual orexin receptor antagonist, conclusively validates orexin signalling mechanism as a specific and effective target for the treatment of insomnia and potentially other disorders in which sleep/wake dysregulation occurs. Also, it is being investigated as a possible agent against diabetic neuropathies, major depressive disorder and for the a migraine prophylaxis. Detected adverse events are: sleep-onset paralysis, excessive daytime sleepiness. As of May 2015, filorexant is no longer listed on Merck's online development pipeline.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Orexin receptor 1 6 Target ID: CHEMBL5113 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22019562	Antagonist 2778		2.5 nM [Ki]
Orexin receptor 2 8 Target ID: CHEMBL4792 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22019562	Antagonist 2778		0.31 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Primary insomnia 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26979830	Primary	Phase II 1132	Unknown Approved Use Unknown
Diabetic neuropathy 23 Sources: http://adisinsight.springer.com/drugs/800031738	Primary	Phase II 1132	Unknown Approved Use Unknown
Migraine 103 Sources: http://adisinsight.springer.com/drugs/800031738 https://www.ncbi.nlm.nih.gov/pubmed/25106663	Preventing	Phase II 1132	Unknown Approved Use Unknown
Major depressive disorder 173 Sources: http://adisinsight.springer.com/drugs/800031738	Primary	Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY34287	https://www.001chemical.com/chem/search?q=DY34287
1PlusChem LLC	1P008TYV	https://www.1pchem.com/search?query=1P008TYV
AK Scientific	Y1891	https://aksci.com/item_detail.php?cat=Y1891
AstaTech	C14152	http://astatechinc.com/CPSResult.php?CRNO=C14152
BLD Pharm	BD287715	http://www.bldpharm.com/search/Search.html?keyword=BD287715
Chem Scene	CS-4437	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-4437
ChemShuttle	186203	https://www.chemshuttle.com/catalogsearch/result/?q=186203
Debye Scientific	DA-47950	https://www.debyesci.com/index.php?id=product&ext[cno]=DA-47950
MedChem Express	HY-15653	https://www.medchemexpress.com/search.html?q=HY-15653&ft=&fa=&fp=
MolPort	MolPort-039-062-223	https://www.molport.com/shop/molecule-link/MolPort-039-062-223
Molcore	MC34287	http://www.molcore.com/CatMC34287.html
ShangHai Biochempartner	BCP000927	http://www.biochempartner.com/search_BCP000927
eMolecules	275091000	https://orderbb.emolecules.com/search/#?query=275091000
eMolecules	301220652	https://orderbb.emolecules.com/search/#?query=301220652
eMolecules	50601859	https://orderbb.emolecules.com/search/#?query=50601859
mcule	MCULE-2170980351	https://mcule.com/MCULE-2170980351/
mcule	MCULE-3186940377	https://mcule.com/MCULE-3186940377/

PubMed

Title	Date	PubMed
Pharmacological characterization of MK-6096 - a dual orexin receptor antagonist for insomnia.	2012 Feb	22019562

Patents

Sample Use Guides

In Vivo Use Guide

2.5 or 5 or 10 or 20mg once daily at bedtime during 4 weeks

Route of Administration: Oral

In Vitro Use Guide

MK-6096 showed radioligand displacement to occupy OX2R in transgenic rat brain in a dose-dependent manner. Following peripheral dosing, MK-6096 achieved 90% occupancy at an exposure of 142 nM in plasma, showing 3-14 fold higher potency than DORA-22 (Occ90 = 1139 nM) and almorexant (Occ90 = 1922 nM) .

Name

Type

Language

FILOREXANT

Official Name

English

METHANONE, ((2R,5R)-5-(((5-FLUORO-2-PYRIDINYL)OXY)METHYL)-2-METHYL-1-PIPERIDINYL)(5-METHYL-2-(2-PYRIMIDINYL)PHENYL)-

Systematic Name

English

filorexant [INN]

Common Name

English

FILOREXANT [USAN]

Common Name

English

MK-6096

Code

English

Filorexant [WHO-DD]

Common Name

English

[(2R,5R)-5-{[(5-Fluoropyridin-2-yl)oxy]methyl}-2-methylpiperidin-1-yl][5-methyl-2-(pyrimidin-2-yl)phenyl]methanone

Systematic Name

English

Code System Code Type Description

CAS

1088991-73-4