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MedKoo Cat#: 319647 | Name: Lemborexant

Description:

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

Lemborexant (INN) (code name E-2006, brand name Dayvigo) is a dual antagonist of the orexin OX1 and OX2 receptors which is under development by Eisai for the treatment of insomnia. Lemborexant was approved by the FDA for adults with insomnia in December 2019. It is a Schedule IV controlled substance.

Chemical Structure

Lemborexant
Lemborexant
CAS#1369764-02-2

Theoretical Analysis

MedKoo Cat#: 319647

Name: Lemborexant

CAS#: 1369764-02-2

Chemical Formula: C22H20F2N4O2

Exact Mass: 410.1554

Molecular Weight: 410.42

Elemental Analysis: C, 64.38; H, 4.91; F, 9.26; N, 13.65; O, 7.80

Price and Availability

This product was removed for the commercial reasons.
Related CAS #
No Data
Synonym
E-2006; E 2006; E2006; Lemborexant; Dayvigo.
IUPAC/Chemical Name
(1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide
InChi Key
MUGXRYIUWFITCP-PGRDOPGGSA-N
InChi Code
InChI=1S/C22H20F2N4O2/c1-13-19(11-25-14(2)27-13)30-12-22(15-4-3-5-16(23)8-15)9-18(22)21(29)28-20-7-6-17(24)10-26-20/h3-8,10-11,18H,9,12H2,1-2H3,(H,26,28,29)/t18-,22+/m0/s1
SMILES Code
O=C([C@H]1[C@@](C2=CC=CC(F)=C2)(COC3=CN=C(C)N=C3C)C1)NC4=NC=C(F)C=C4
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 410.42 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: Rosenberg R, Murphy P, Zammit G, Mayleben D, Kumar D, Dhadda S, Filippov G, LoPresti A, Moline M. Comparison of Lemborexant With Placebo and Zolpidem Tartrate Extended Release for the Treatment of Older Adults With Insomnia Disorder: A Phase 3 Randomized Clinical Trial. JAMA Netw Open. 2019 Dec 2;2(12):e1918254. doi: 10.1001/jamanetworkopen.2019.18254. PubMed PMID: 31880796. 2: Mahoney CE, Mochizuki T, Scammell TE. Dual orexin receptor antagonists increase sleep and cataplexy in wild type mice. Sleep. 2019 Dec 13. pii: zsz302. doi: 10.1093/sleep/zsz302. [Epub ahead of print] PubMed PMID: 31830270. 3: Beuckmann CT, Ueno T, Nakagawa M, Suzuki M, Akasofu S. Preclinical in vivo characterization of lemborexant (E2006), a novel dual orexin receptor antagonist for sleep/wake regulation. Sleep. 2019 Jun 11;42(6). pii: zsz076. doi: 10.1093/sleep/zsz076. PubMed PMID: 30923834; PubMed Central PMCID: PMC6559177. 4: Vermeeren A, Jongen S, Murphy P, Moline M, Filippov G, Pinner K, Perdomo C, Landry I, Majid O, Van Oers ACM, Van Leeuwen CJ, Ramaekers JG, Vuurman EFPM. On-the-road driving performance the morning after bedtime administration of lemborexant in healthy adult and elderly volunteers. Sleep. 2019 Apr 1;42(4). pii: zsy260. doi: 10.1093/sleep/zsy260. PubMed PMID: 30597112; PubMed Central PMCID: PMC6448281. 5: 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. Review. PubMed PMID: 30058034. 6: Ueno T, Ishida T, Kusano K. Disposition and metabolism of [(14)C]lemborexant, a novel dual orexin receptor antagonist, in rats and monkeys. Xenobiotica. 2019 Jun;49(6):688-697. doi: 10.1080/00498254.2018.1482509. Epub 2018 Jul 5. PubMed PMID: 29806508. 7: Murphy P, Moline M, Mayleben D, Rosenberg R, Zammit G, Pinner K, Dhadda S, Hong Q, Giorgi L, Satlin A. Lemborexant, A Dual Orexin Receptor Antagonist (DORA) for the Treatment of Insomnia Disorder: Results From a Bayesian, Adaptive, Randomized, Double-Blind, Placebo-Controlled Study. J Clin Sleep Med. 2017 Nov 15;13(11):1289-1299. doi: 10.5664/jcsm.6800. PubMed PMID: 29065953; PubMed Central PMCID: PMC5656478. 8: Beuckmann CT, Suzuki M, Ueno T, Nagaoka K, Arai T, Higashiyama H. In Vitro and In Silico Characterization of Lemborexant (E2006), a Novel Dual Orexin Receptor Antagonist. J Pharmacol Exp Ther. 2017 Aug;362(2):287-295. doi: 10.1124/jpet.117.241422. Epub 2017 May 30. PubMed PMID: 28559480. 9: Murphy PJ, Yasuda S, Nakai K, Yoshinaga T, Hall N, Zhou M, Aluri J, Rege B, Moline M, Ferry J, Darpo B. Concentration-Response Modeling of ECG Data From Early-Phase Clinical Studies as an Alternative Clinical and Regulatory Approach to Assessing QT Risk - Experience From the Development Program of Lemborexant. J Clin Pharmacol. 2017 Jan;57(1):96-104. doi: 10.1002/jcph.785. Epub 2016 Aug 4. PubMed PMID: 27338807.