Filorexant

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]

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
PDB ligand	NT5 (PDBe, RCSB PDB)
CompTox Dashboard (EPA)	DTXSID50148764
ECHA InfoCard	100.203.042
Chemical and physical data
Formula	C24H25FN4O2
Molar mass	420.488 g·mol^−1
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

See also

• List of investigational sleep drugs

References

1. Hoyer D, Jacobson LH (December 2013). "Orexin in sleep, addiction and more: is the perfect insomnia drug at hand?". Neuropeptides. 47 (6): 477–88. doi:10.1016/j.npep.2013.10.009. PMID 24215799. S2CID 6402764.
2. 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. doi:10.1016/j.neuropharm.2011.10.003. PMID 22019562. S2CID 35304627.
3. Peroutka SJ (January 2014). "Clinical trials update. 2013: year in review". Headache. 54 (1): 189–94. doi:10.1111/head.12267. PMID 24400767.
4. Cooper CK (March 2014). "Orexin Receptor Antagonists: Novel Hypnotic Agents". Ment. Health Clin. 4 (2): 64. doi:10.9740/mhc.n190094. ISSN 2168-9709.
5. Chabi, A.; Zhang, Y.; Jackson, S.; Cady, R.; Lines, C.; Herring, W. J.; Connor, K. M.; Michelson, D. (Aug 8, 2014). "Randomized controlled trial of the orexin receptor antagonist filorexant for migraine prophylaxis". Cephalalgia. 35 (5): 379–88. doi:10.1177/0333102414544979. PMID 25106663. S2CID 20872932.
6. 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.
7. "Merck Pipeline". Merck. 2015. Retrieved 2015-05-14.

External links

• Filorexant - AdisInsight