Filorexant

Chemical compound From Wikipedia, the free encyclopedia

Filorexant (INNTooltip International Nonproprietary Name, USANTooltip United States Approved Name; developmental code name MK-6096) is an orexin antagonist which was under development by Merck for the treatment of insomnia, depression, diabetic neuropathy, and migraine.[2][3] It is a dual antagonist of the orexin OX1 and OX2 receptors.[4][5] It has a relatively short elimination half-life of 3 to 6 hours.[1] However, it dissociates slowly from the orexin receptors and may thereby have a longer duration.[6] Possibly in relation to this, filorexant shows next-day somnolence similarly to suvorexant.[6] In phase 2 clinical trials, filorexant was found to be effective in the treatment of insomnia,[7] but was not effective in the treatment of major depressive disorder,[8][9][10] painful diabetic neuropathy,[11][12] or migraine.[13] As of May 2015, filorexant was no longer listed on Merck's online development pipeline and hence development of the drug appears to have been discontinued.[14][1][2] Development of filorexant may have been discontinued due to lack of differentiation from suvorexant (which was also developed by Merck).[6]

Other namesMK-6096; MK6096
Routes of
administrationBy mouth
Drug classOrexin antagonist
ATC code
  • None
Quick facts Clinical data, Other names ...
Filorexant
Clinical data
Other namesMK-6096; MK6096
Routes of
administration		By mouth
Drug classOrexin antagonist
ATC code
  • None
Pharmacokinetic data
Elimination half-life3–6 hours[1]
Identifiers
  • [(2R,5R)-5-{[(5-Fluoro-2-pyridinyl)oxy]methyl}-2-methyl-1-piperidinyl][5-methyl-2-(2-pyrimidinyl)phenyl]methanone
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.203.042 Edit this at Wikidata
Chemical and physical data
FormulaC24H25FN4O2
Molar mass420.488 g·mol−1
3D model (JSmol)
  • C[C@@H]1CC[C@H](CN1C(=O)C2=C(C=CC(=C2)C)C3=NC=CC=N3)COC4=NC=C(C=C4)F
  • 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
  • Key:NPFDWHQSDBWQLH-QZTJIDSGSA-N
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