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Lemborexant

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Also known as: 1369764-02-2, Dayvigo, E-2006, E2006, 0k5743g68x, (1r,2s)-2-[(2,4-dimethylpyrimidin-5-yl)oxymethyl]-2-(3-fluorophenyl)-n-(5-fluoropyridin-2-yl)cyclopropane-1-carboxamide

Molecular Formula

C₂₂H₂₀F₂N₄O₂

Molecular Weight

410.4 g/mol

InChI Key

MUGXRYIUWFITCP-PGRDOPGGSA-N

FDA UNII

0K5743G68X

Lemborexant is a novel dual orexin receptor antagonist used in the treatment of insomnia characterized by difficulties with sleep onset and/or sleep maintenance. Recent research in the field of sleep disorders has revealed that insomnia is likely driven not by the inability of the brain to "switch on" sleep-related circuits, but rather an inability to "switch-off" wake-promoting circuits. Whereas historically popular pharmacologic treatments for insomnia (e.g. [zopiclone], [zolpidem], benzodiazepines) focus on enhancing sleep drive via modulation of GABA and melatonin receptors, lemborexant and other orexin antagonists (e.g. [suvorexant]) act to counteract inappropriate wakefulness. This novel mechanism of action offers potential advantages over classic hypnotic agents, including a more favorable adverse effect profile and potentially greater efficacy, and may signal the beginning of a new wave of treatment options for patients suffering from insomnia.

Lemborexant is an Orexin Receptor Antagonist. The mechanism of action of lemborexant is as an Orexin Receptor Antagonist, and Cytochrome P450 2B6 Inducer.

1 2D Structure

Lemborexant

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,2S)-2-[(2,4-dimethylpyrimidin-5-yl)oxymethyl]-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropane-1-carboxamide

2.1.2 InChI

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

2.1.3 InChI Key

MUGXRYIUWFITCP-PGRDOPGGSA-N

2.1.4 Canonical SMILES

CC1=NC(=NC=C1OCC2(CC2C(=O)NC3=NC=C(C=C3)F)C4=CC(=CC=C4)F)C

2.1.5 Isomeric SMILES

CC1=NC(=NC=C1OC[C@]2(C[C@H]2C(=O)NC3=NC=C(C=C3)F)C4=CC(=CC=C4)F)C

2.2 Other Identifiers

2.2.1 UNII

0K5743G68X

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (1r,2s)-2-(((2,4-dimethyl-5-pyrimidinyl)oxy)methyl)-2-(3-fluorophenyl)-n-(5-fluoro-2-pyridinyl)cyclopropanecarboxamide

2. Cyclopropanecarboxamide, 2-(((2,4-dimethyl-5-pyrimidinyl)oxy)methyl)-2-(3-fluorophenyl)-n-(5-fluoro-2-pyridinyl)-, (1r,2s)-

3. Dayvigo

2.3.2 Depositor-Supplied Synonyms

1. 1369764-02-2

2. Dayvigo

3. E-2006

4. E2006

5. 0k5743g68x

6. (1r,2s)-2-[(2,4-dimethylpyrimidin-5-yl)oxymethyl]-2-(3-fluorophenyl)-n-(5-fluoropyridin-2-yl)cyclopropane-1-carboxamide

7. (1r,2s)-2-(((2,4-dimethylpyrimidin-5-yl)oxy)methyl)-2-(3-fluorophenyl)-n-(5-fluoropyridin-2-yl)cyclopropanecarboxamide

8. Cyclopropanecarboxamide, 2-(((2,4-dimethyl-5-pyrimidinyl)oxy)methyl)-2-(3-fluorophenyl)-n-(5-fluoro-2-pyridinyl)-, (1r,2s)-

9. (1~{r},2~{s})-2-[(2,4-dimethylpyrimidin-5-yl)oxymethyl]-~{n}-(5-fluoranylpyridin-2-yl)-2-(3-fluorophenyl)cyclopropane-1-carboxamide

10. E 2006

11. Lemborexant [usan:inn]

12. Unii-0k5743g68x

13. (1r,2s)-2-(((2,4-dimethyl-5-pyrimidinyl)oxy)methyl)-2-(3-fluorophenyl)-n-(5-fluoro-2-pyridinyl)cyclopropanecarboxamide

14. (1r,2s)-2-((2,4-dimethylpyrimidin-5-yl)oxymethyl)-2-(3-fluorophenyl)-n-(5-fluoropyridin-2-yl)cyclopropane-1-carboxamide

15. (1r,2s)-2-[[(2,4-dimethyl-5-pyrimidinyl)oxy]methyl]-2-(3-fluorophenyl)-n-(5-fluoro-2-pyridinyl)cyclopropanecarboxamide

16. Cyclopropanecarboxamide, 2-[[(2,4-dimethyl-5-pyrimidinyl)oxy]methyl]-2-(3-fluorophenyl)-n-(5-fluoro-2-pyridinyl)-, (1r,2s)-

17. Dayvigo (tn)

18. Lemborexant [inn]

19. Lemborexant(e2006)

20. Lemborexant [mi]

21. Lemborexant; E-2006

22. Lemborexant [jan]

23. Lemborexant [usan]

24. Lemborexant [who-dd]

25. Lemborexant (jan/usan/inn)

26. Gtpl9302

27. Schembl2116558

28. Chembl3545367

29. Lemborexant [orange Book]

30. Dtxsid401027940

31. Amy27888

32. Ex-a2337

33. Bdbm50093793

34. Zinc118073503

35. Db11951

36. Compound 34 [pmid: 25953512]

37. Ncgc00488783-01

38. Ac-30918

39. Hy-16725

40. J3.610.985h

41. D11022

42. E-2006e-2006

43. A886588

44. Q20707990

45. (1r,2s)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(3-fluorophenyl)-n-(5-fluoropyridin-2-yl)cyclopropane-1-carboxamide

2.4 Create Date

2012-04-23

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₀F₂N₄O₂
Molecular Weight	410.4 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	6
Exact Mass	410.15543222 g/mol
Monoisotopic Mass	410.15543222 g/mol
Topological Polar Surface Area	77 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	612
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Lemborexant is indicated for the treatment of adult patients with insomnia characterized by difficulties with sleep onset and/or sleep maintenance.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Lemborexant promotes sleep by antagonizing the actions of wake-promoting chemicals in the brain. Episodes of complex sleep behaviors (e.g. eating food, having sex, making phone calls) have been reported in patients using lemborexant - these events may occur in hypnotic-naive and hyponotic-experienced patients, and patients are unlikely to remember these events. Patients exhibiting complex sleep behaviors should discontinue lemborexant immediately. Lemborexant may carry some risk of abuse, and should be used with caution in patients with a history of alcohol or drug addiction. Its controlled substance schedule is currently under review by the Drug Enforcement Administration.

5.2 MeSH Pharmacological Classification

Orexin Receptor Antagonists

Substances that bind to and inhibit the action of OREXIN RECEPTORS. Drugs in this class have been used as SLEEP AIDS, PHARMACEUTICAL. (See all compounds classified as Orexin Receptor Antagonists.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

LEMBOREXANT

5.3.2 FDA UNII

0K5743G68X

5.3.3 Pharmacological Classes

Orexin Receptor Antagonist [EPC]; Orexin Receptor Antagonists [MoA]; Cytochrome P450 2B6 Inducers [MoA]

5.4 ATC Code

N - Nervous system

N05 - Psycholeptics

N05C - Hypnotics and sedatives

N05CM - Other hypnotics and sedatives

N05CM21 - Lemborexant

5.5 Absorption, Distribution and Excretion

Absorption

Animal models of lemborexant disposition have demonstrated rapid absorption following oral administration. The T_max of lemborexant is approximately 1-3 hours, or 3-5 hours following administration of a high-fat, high-calorie meal. C_max and AUC_0-24h increase at a rate slightly less than proportionate to the given dose. Following administration of a high-fat, high-calorie meal, C_max is decreased by 23% and AUC_0-inf is increased by 18%. AUC, C_max, and terminal half-life are increased in the presence of moderate hepatic impairment, and AUC (but not half-life) is increased in the presence of mild hepatic impairment.

Route of Elimination

Following oral administration, 57.4% of the dose is found in the feces and 29.1% in the urine. Less than 1% of the dose recovered in the urine exists as unchanged parent drug, suggesting extensive metabolism.

Volume of Distribution

The volume of distribution of lemborexant is 1970 L, indicating extensive tissue distribution.

5.6 Metabolism/Metabolites

Given that less than 1% of an administered dose is recovered unchanged in the urine, it is likely that lemborexant is extensively metabolized - this has been confirmed in rat and monkey models, but its metabolism in humans has not been fully characterized. Prescribing information states that it is predominantly metabolized by CYP3A4, with a smaller contribution by CYP3A5. The major circulating metabolite is lemborexant's M10 metabolite, which is pharmacologically active and binds to orexin receptors with a similar affinity to the parent drug. The M10 metabolite has the potential to induce CYP3A and CYP2B6 enzymes, weakly inhibit CYP3A enzymes, and is a substrate of P-gp transporters.

5.7 Biological Half-Life

The half-life for lemborexant at doses of 5mg and 10mg is 17 and 19 hours, respectively.

5.8 Mechanism of Action

The orexin neuropeptide signaling system is involved in many physiologic functions, including sleep/wake control. Orexin-A and orexin-B activate post-synaptic G-protein coupled orexin-1 receptors (OX1R) and orexin-2 receptors (OX2R), which are found on neurons in the hypothalamus that project to numerous wake-controlling nuclei. Each receptor carries slightly different activity - activation of OX1R appears to suppress the onset of rapid eye movement (REM) sleep, whereas activation of OX2R appears to suppress non-REM sleep. Lemborexant is an competitive antagonist of OX1R and OX2R. By blocking the binding of wake-promoting orexin-A and -B at these receptors, lemborexant suppresses the wake-drive, thereby promoting sleep.

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