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MedKoo Cat#: 319697 | Name: Filorexant
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Filorexant, also known as MK6096, is an orally bioavailable potent and selective reversible antagonist of OX(1)R and OX(2)R currently in clinical development for insomnia. MK-6096 demonstrated potent binding and antagonism of both human OX(1)R and OX(2)R (<3 nM in binding, 11 nM in FLIPR), with no significant off-target activities against a panel of >170 receptors and enzymes. MK-6096 occupies 90% of human OX(2)Rs expressed in transgenic rats at a plasma concentration of 142 nM, and dose-dependently reduced locomotor activity and significantly increased sleep in rats (3-30 mg/kg) and dogs (0.25 and 0.5 mg/kg).

Chemical Structure

Filorexant
Filorexant
CAS#1088991-73-4

Theoretical Analysis

MedKoo Cat#: 319697

Name: Filorexant

CAS#: 1088991-73-4

Chemical Formula: C24H25FN4O2

Exact Mass: 420.1962

Molecular Weight: 420.49

Elemental Analysis: C, 68.55; H, 5.99; F, 4.52; N, 13.32; O, 7.61

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 650.00 2 Weeks
25mg USD 1,250.00 2 Weeks
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Related CAS #
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Synonym
MK6096; MK-6096; MK 6096; Filorexant; filorexantum
IUPAC/Chemical Name
((2R,5R)-5-(((5-fluoropyridin-2-yl)oxy)methyl)-2-methylpiperidin-1-yl)(5-methyl-2-(pyrimidin-2-yl)phenyl)methanone
InChi Key
NPFDWHQSDBWQLH-QZTJIDSGSA-N
InChi Code
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
SMILES Code
O=C(N1[C@H](C)CC[C@@H](COC2=NC=C(F)C=C2)C1)C3=CC(C)=CC=C3C4=NC=CC=N4
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 420.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Wu X, Xue T, Chen Z, Wang Z, Chen G. Orexin Receptor Antagonists and Insomnia. Curr Psychiatry Rep. 2022 Oct;24(10):509-521. doi: 10.1007/s11920-022-01357-w. Epub 2022 Aug 16. PMID: 35972717. 2: Abad VC, Guilleminault C. Insomnia in Elderly Patients: Recommendations for Pharmacological Management. Drugs Aging. 2018 Sep;35(9):791-817. doi: 10.1007/s40266-018-0569-8. PMID: 30058034. 3: Moreno-Ajona D, Villar-Martínez MD, Goadsby PJ. Emerging Targets for Migraine Treatment. Neurol India. 2021 Mar-Apr;69(Supplement):S98-S104. doi: 10.4103/0028-3886.315989. PMID: 34003154. 4: Chabi A, Zhang Y, Jackson S, Cady R, Lines C, Herring WJ, Connor KM, Michelson D. Randomized controlled trial of the orexin receptor antagonist filorexant for migraine prophylaxis. Cephalalgia. 2015 Apr;35(5):379-88. doi: 10.1177/0333102414544979. Epub 2014 Aug 8. PMID: 25106663. 5: Joseph Herring W, Ge JY, Jackson S, Assaid C, Connor KM, Michelson D. Orexin Receptor Antagonism in Painful Diabetic Neuropathy: A Phase 2 Trial With Filorexant. Clin J Pain. 2018 Jan;34(1):37-43. doi: 10.1097/AJP.0000000000000503. PMID: 28448426. 6: Connor KM, Ceesay P, Hutzelmann J, Snavely D, Krystal AD, Trivedi MH, Thase M, Lines C, Herring WJ, Michelson D. Phase II Proof-of-Concept Trial of the Orexin Receptor Antagonist Filorexant (MK-6096) in Patients with Major Depressive Disorder. Int J Neuropsychopharmacol. 2017 Aug 1;20(8):613-618. doi: 10.1093/ijnp/pyx033. PMID: 28582570; PMCID: PMC5570043. 7: Connor KM, Mahoney E, Jackson S, Hutzelmann J, Zhao X, Jia N, Snyder E, Snavely D, Michelson D, Roth T, Herring WJ. A Phase II Dose-Ranging Study Evaluating the Efficacy and Safety of the Orexin Receptor Antagonist Filorexant (MK-6096) in Patients with Primary Insomnia. Int J Neuropsychopharmacol. 2016 Aug 12;19(8):pyw022. doi: 10.1093/ijnp/pyw022. PMID: 26979830; PMCID: PMC5006195. 8: Sun S, Fu J. Methyl-containing pharmaceuticals: Methylation in drug design. Bioorg Med Chem Lett. 2018 Nov 1;28(20):3283-3289. doi: 10.1016/j.bmcl.2018.09.016. Epub 2018 Sep 14. PMID: 30243589. 9: Kuduk SD, Skudlarek JW, Di Marco CN, Bruno JG, Pausch MA, O'Brien JA, Cabalu TD, Stevens J, Brunner J, Tannenbaum PL, Gotter AL, Winrow CJ, Renger JJ, Coleman PJ. Synthesis and evaluation of carbon-linked analogs of dual orexin receptor antagonist filorexant. Bioorg Med Chem Lett. 2014 Apr 1;24(7):1784-9. doi: 10.1016/j.bmcl.2014.02.026. Epub 2014 Feb 19. PMID: 24630562. 10: Raheem IT, Breslin MJ, Bruno J, Cabalu TD, Cooke A, Cox CD, Cui D, Garson S, Gotter AL, Fox SV, Harrell CM, Kuduk SD, Lemaire W, Prueksaritanont T, Renger JJ, Stump C, Tannenbaum PL, Williams PD, Winrow CJ, Coleman PJ. Discovery of piperidine ethers as selective orexin receptor antagonists (SORAs) inspired by filorexant. Bioorg Med Chem Lett. 2015 Feb 1;25(3):444-50. doi: 10.1016/j.bmcl.2014.12.056. Epub 2014 Dec 23. PMID: 25577040. 11: Zisapel N. Current Phase II investigational therapies for insomnia. Expert Opin Investig Drugs. 2015 Mar;24(3):401-11. doi: 10.1517/13543784.2015.987340. Epub 2014 Nov 25. PMID: 25423562. 12: Hoyer D, Jacobson LH. Orexin in sleep, addiction and more: is the perfect insomnia drug at hand? Neuropeptides. 2013 Dec;47(6):477-88. doi: 10.1016/j.npep.2013.10.009. Epub 2013 Oct 23. PMID: 24215799. 13: Janto K, Prichard JR, Pusalavidyasagar S. An Update on Dual Orexin Receptor Antagonists and Their Potential Role in Insomnia Therapeutics. J Clin Sleep Med. 2018 Aug 15;14(8):1399-1408. doi: 10.5664/jcsm.7282. PMID: 30092886; PMCID: PMC6086961. 14: Maness EB, Blumenthal SA, Burk JA. Dual orexin/hypocretin receptor antagonism attenuates attentional impairments in an NMDA receptor hypofunction model of schizophrenia. bioRxiv [Preprint]. 2023 Feb 5:2023.02.05.527043. doi: 10.1101/2023.02.05.527043. Update in: Behav Brain Res. 2023 May 16;450:114497. PMID: 36778441; PMCID: PMC9915718. 15: Maness EB, Blumenthal SA, Burk JA. Dual orexin/hypocretin receptor antagonism attenuates NMDA receptor hypofunction-induced attentional impairments in a rat model of schizophrenia. Behav Brain Res. 2023 Jul 26;450:114497. doi: 10.1016/j.bbr.2023.114497. Epub 2023 May 16. PMID: 37196827; PMCID: PMC10330488. 16: Goadsby PJ. Putting migraine to sleep: Rexants as a preventive strategy. Cephalalgia. 2015 Apr;35(5):377-8. doi: 10.1177/0333102414566196. Epub 2015 Jan 9. PMID: 25576464. 17: Lionetto L, Negro A, Palmisani S, Gentile G, Del Fiore MR, Mercieri M, Simmaco M, Smith T, Al-Kaisy A, Arcioni R, Martelletti P. Emerging treatment for chronic migraine and refractory chronic migraine. Expert Opin Emerg Drugs. 2012 Sep;17(3):393-406. doi: 10.1517/14728214.2012.709846. Epub 2012 Aug 3. PMID: 22862686. 18: Pałasz A, Lapray D, Peyron C, Rojczyk-Gołębiewska E, Skowronek R, Markowski G, Czajkowska B, Krzystanek M, Wiaderkiewicz R. Dual orexin receptor antagonists - promising agents in the treatment of sleep disorders. Int J Neuropsychopharmacol. 2014 Jan;17(1):157-68. doi: 10.1017/S1461145713000552. Epub 2013 May 23. Erratum in: Int J Neuropsychopharmacol. 2016;19(3). pii: pyw005. doi: 10.1093/ijnp/pyw005. PMID: 23702225. 19: Fagan H, Jones E, Baldwin DS. Orexin Receptor Antagonists in the Treatment of Depression: A Leading Article Summarising Pre-clinical and Clinical Studies. CNS Drugs. 2023 Jan;37(1):1-12. doi: 10.1007/s40263-022-00974-6. Epub 2022 Nov 27. PMID: 36436175. 20: Kuduk SD, Skudlarek JW, DiMarco CN, Bruno JG, Pausch MH, O'Brien JA, Cabalu TD, Stevens J, Brunner J, Tannenbaum PL, Garson SL, Savitz AT, Harrell CM, Gotter AL, Winrow CJ, Renger JJ, Coleman PJ. Identification of MK-8133: An orexin-2 selective receptor antagonist with favorable development properties. Bioorg Med Chem Lett. 2015 Jun 15;25(12):2488-92. doi: 10.1016/j.bmcl.2015.04.066. Epub 2015 Apr 29. PMID: 25981685.

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