Filorexant

Filorexant
Clinical data
ATC code	none;
Identifiers
	IUPAC name [(2R,5R)-5-{[(5-Fluoro-2-pyridinyl)oxy]methyl}-2-methyl-1-piperidinyl][5-methyl-2-(2-pyrimidinyl)phenyl]methanone;
CAS Number	1088991-73-4 ;
PubChem CID	25128145;
ChemSpider	28528372;
UNII	E6BTT8VA5Z;
KEGG	D10345;
Chemical and physical data
Formula	C24H25FN4O2
Molar mass	420.479 g/mol
3D model (JSmol)	Interactive image;
	SMILES 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 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 ;

Filorexant (INN, USAN) (code name MK-6096) is an orexin antagonist which is or was under development by Merck for the treatment of insomnia.^[1] It is a dual antagonist of the OX₁ and OX₂ receptors.^[2]^[3] As of March 2014, filorexant has completed phase II clinical trials.^[4] It was also investigated as a migraine prophylaxis, but was not found effective,^[5] and in major depressive disorder and painful diabetic neuropathy.^[6] As of May 2015, filorexant is no longer listed on Merck's online development pipeline.^[7]

References[edit]

^ Hoyer D, Jacobson LH (December 2013). "Orexin in sleep, addiction and more: is the perfect insomnia drug at hand?". Neuropeptides. 47 (6): 477–88. PMID 24215799. doi:10.1016/j.npep.2013.10.009.
^ Winrow CJ, Gotter AL, Cox CD, et al. (February 2012). "Pharmacological characterization of MK-6096 - a dual orexin receptor antagonist for insomnia". Neuropharmacology. 62 (2): 978–87. PMID 22019562. doi:10.1016/j.neuropharm.2011.10.003.
^ Peroutka SJ (January 2014). "Clinical trials update. 2013: year in review". Headache. 54 (1): 189–94. PMID 24400767. doi:10.1111/head.12267.
^ Cooper CK (March 2014). "Orexin Receptor Antagonists: Novel Hypnotic Agents". Ment. Health. Clin. 4 (2): 64. ISSN 2168-9709.
^ "Randomized controlled trial of the orexin receptor antagonist filorexant for migraine prophylaxis.". Cephalalgia. 35: 379–88. Aug 8, 2014. PMID 25106663. doi:10.1177/0333102414544979.
^ Michel Alexander Steiner; Christopher J Winrow (11 November 2014). Insomnia and beyond - Exploring the therapeutic potential of orexin receptor antagonists. Frontiers E-books. pp. 3–. ISBN 978-2-88919-330-1.
^ "Merck Pipeline". Merck. 2015. Retrieved 2015-05-14.

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Clinical data

ATC code	none
Identifiers
IUPAC name [(2R,5R)-5-{[(5-Fluoro-2-pyridinyl)oxy]methyl}-2-methyl-1-piperidinyl][5-methyl-2-(2-pyrimidinyl)phenyl]methanone
CAS Number	1088991-73-4^Y
PubChem CID	25128145
ChemSpider	28528372
UNII	E6BTT8VA5Z
KEGG	D10345
Chemical and physical data
Formula	C₂₄H₂₅FN₄O₂
Molar mass	420.479 g/mol
3D model (JSmol)	Interactive image
SMILES 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 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