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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 of FILOREXANT

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.5 nM [Ki]
0.31 nM [Ki]
Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
Pharmacological characterization of MK-6096 - a dual orexin receptor antagonist for insomnia.
2012 Feb
Patents

Sample Use Guides

2.5 or 5 or 10 or 20mg once daily at bedtime during 4 weeks
Route of Administration: Oral
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
INN   USAN   WHO-DD  
USAN   INN  
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
Created by admin on Sat Dec 16 06:48:49 GMT 2023 , Edited by admin on Sat Dec 16 06:48:49 GMT 2023
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WIKIPEDIA
Filorexant
Created by admin on Sat Dec 16 06:48:49 GMT 2023 , Edited by admin on Sat Dec 16 06:48:49 GMT 2023
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USAN
ZZ-36
Created by admin on Sat Dec 16 06:48:49 GMT 2023 , Edited by admin on Sat Dec 16 06:48:49 GMT 2023
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FDA UNII
E6BTT8VA5Z
Created by admin on Sat Dec 16 06:48:49 GMT 2023 , Edited by admin on Sat Dec 16 06:48:49 GMT 2023
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DRUG BANK
DB12158
Created by admin on Sat Dec 16 06:48:49 GMT 2023 , Edited by admin on Sat Dec 16 06:48:49 GMT 2023
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EPA CompTox
DTXSID50148764
Created by admin on Sat Dec 16 06:48:49 GMT 2023 , Edited by admin on Sat Dec 16 06:48:49 GMT 2023
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NCI_THESAURUS
C169980
Created by admin on Sat Dec 16 06:48:49 GMT 2023 , Edited by admin on Sat Dec 16 06:48:49 GMT 2023
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INN
9671
Created by admin on Sat Dec 16 06:48:49 GMT 2023 , Edited by admin on Sat Dec 16 06:48:49 GMT 2023
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PUBCHEM
25128145
Created by admin on Sat Dec 16 06:48:49 GMT 2023 , Edited by admin on Sat Dec 16 06:48:49 GMT 2023
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SMS_ID
300000034195
Created by admin on Sat Dec 16 06:48:49 GMT 2023 , Edited by admin on Sat Dec 16 06:48:49 GMT 2023
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ChEMBL
CHEMBL2107822
Created by admin on Sat Dec 16 06:48:49 GMT 2023 , Edited by admin on Sat Dec 16 06:48:49 GMT 2023
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