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Tasimelteon

Tasimelteon

Synopsis, Chemistry

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Also known as: 609799-22-6, Hetlioz, Vec-162, Bms-214778, Vec 162, Bms 214778

Molecular Formula

C₁₅H₁₉NO₂

Molecular Weight

245.32 g/mol

InChI Key

PTOIAAWZLUQTIO-GXFFZTMASA-N

FDA UNII

SHS4PU80D9

Tasimelteon is a selective dual melatonin receptor agonist indicated for the treatment of Non-24-Hour Sleep-Wake Disorder (N24HSWD). Occurring commonly in blind individuals without light perception, this condition is often characterized by periods of night-time insomnia and day-time sleepiness. In blind individuals, a lack of light stimulation causes an extension of the 24-hour circadian cycle and can lead to progressively delayed sleep onset. By activating melatonin receptors MT1 and MT2 in the suprachiasmatic nucleus of the brain, tasimelteon has been shown to improve sleep by resynchronizing the circadian rhythm through its "non-photic" mechanism. Tasimelteon is currently the only drug available for the treatment of N24HSWD and was granted orphan drug status by the FDA in 2010.

Tasimelteon is a Melatonin Receptor Agonist. The mechanism of action of tasimelteon is as a Melatonin Receptor Agonist.

1 2D Structure

Tasimelteon

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl]propanamide

2.1.2 InChI

InChI=1S/C15H19NO2/c1-2-15(17)16-9-10-8-13(10)11-4-3-5-14-12(11)6-7-18-14/h3-5,10,13H,2,6-9H2,1H3,(H,16,17)/t10-,13+/m0/s1

2.1.3 InChI Key

PTOIAAWZLUQTIO-GXFFZTMASA-N

2.1.4 Canonical SMILES

CCC(=O)NCC1CC1C2=C3CCOC3=CC=C2

2.1.5 Isomeric SMILES

CCC(=O)NC[C@@H]1C[C@H]1C2=C3CCOC3=CC=C2

2.2 Other Identifiers

2.2.1 UNII

SHS4PU80D9

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bms 214778

2. Bms-214778

3. Bms214778

4. N-((2-(2,3-dihydro-4-benzofuranyl)cyclopropyl)methyl)propanamide

2.3.2 Depositor-Supplied Synonyms

1. 609799-22-6

2. Hetlioz

3. Vec-162

4. Bms-214778

5. Vec 162

6. Bms 214778

7. Shs4pu80d9

8. Chebi:79042

9. Bms214778

10. Bms-214,778

11. N-(((1r,2r)-2-(2,3-dihydrobenzofuran-4-yl)cyclopropyl)methyl)propionamide

12. N-[[(1r,2r)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl]propanamide

13. N-{[(1r,2r)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl}propanamide

14. N-(((1r,2r)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl)methyl)propanamide

15. Propanamide, N-(((1r,2r)-2-(2,3-dihydro-4-benzofuranyl)cyclopropyl)methyl)-

16. Tasimelteon [usan]

17. Tasimelteon [usan:inn]

18. Unii-shs4pu80d9

19. Tasimelteonum

20. N-([(1r,2r)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl)propanamide

21. Hetlioz (tn)

22. Hetlioz Lq

23. Tasimelteon [mi]

24. Tasimelteon [inn]

25. Tasimelteon (usan/inn)

26. Tasimelteon [vandf]

27. Tasimelteon [mart.]

28. Tasimelteon [who-dd]

29. Gtpl7393

30. Schembl3505912

31. Chembl2103822

32. Tasimelteon, >=98% (hplc)

33. Amy6925

34. Dtxsid70209826

35. Tasimelteon [orange Book]

36. Hms3885l17

37. Act06729

38. Bcp07180

39. Ex-a2729

40. Zinc4392649

41. Mfcd09033789

42. S4281

43. Akos025149360

44. Ac-6143

45. Ccg-266915

46. Cs-5512

47. Db09071

48. Ncgc00522560-01

49. As-35291

50. Hy-14803

51. T3813

52. J3.640.465e

53. D09388

54. 799t226

55. Q7687250

56. N-((2-(2,3-dihydro-4-benzofuranyl)cyclopropyl)methyl)propanamide

57. (trans)-n-[[2-(2,3-dihydrobenzofuran-4-yl) Cyclopropyl]methyl]propanamide

58. (trans)-n-[[2-(2,3-dihydrobenzofuran-4-yl)cyclopropyl]methyl]propanamide

59. (-)-(trans)-n-[[2-(2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl] Methyl]propanamide

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₉NO₂
Molecular Weight	245.32 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	4
Exact Mass	245.141578849 g/mol
Monoisotopic Mass	245.141578849 g/mol
Topological Polar Surface Area	38.3 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	318
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 Information

1 of 2
Drug Name	Hetlioz
PubMed Health	Tasimelteon (By mouth)
Drug Classes	Central Nervous System Agent
Drug Label	HETLIOZ (tasimelteon) is a melatonin receptor agonist, chemically designated as (1R, 2R)-N-[2-(2,3-dihydrobenzofuran-4-yl)cyclopropylmethyl]propanamide, containing two chiral centers. The molecular formula is C15H19NO2, and the molecular weight is 24...
Active Ingredient	Tasimelteon
Dosage Form	Capsule
Route	Oral
Strength	20mg
Market Status	Prescription
Company	Vanda Pharms

2 of 2
Drug Name	Hetlioz
PubMed Health	Tasimelteon (By mouth)
Drug Classes	Central Nervous System Agent
Drug Label	HETLIOZ (tasimelteon) is a melatonin receptor agonist, chemically designated as (1R, 2R)-N-[2-(2,3-dihydrobenzofuran-4-yl)cyclopropylmethyl]propanamide, containing two chiral centers. The molecular formula is C15H19NO2, and the molecular weight is 24...
Active Ingredient	Tasimelteon
Dosage Form	Capsule
Route	Oral
Strength	20mg
Market Status	Prescription
Company	Vanda Pharms

4.2 Drug Indication

Tasimelteon is indicated for the treatment of Non-24-Hour Sleep-Wake Disorder (N24HSWD).

FDA Label

Hetlioz is indicated for the treatment of Non-24-Hour Sleep-Wake Disorder (Non-24) in totally blind adults.

5 Pharmacology and Biochemistry

5.1 FDA Pharmacological Classification

5.1.1 Active Moiety

TASIMELTEON

5.1.2 FDA UNII

SHS4PU80D9

5.1.3 Pharmacological Classes

Melatonin Receptor Agonists [MoA]; Melatonin Receptor Agonist [EPC]

5.2 ATC Code

N05CH

N - Nervous system

N05 - Psycholeptics

N05C - Hypnotics and sedatives

N05CH - Melatonin receptor agonists

N05CH03 - Tasimelteon

5.3 Absorption, Distribution and Excretion

Route of Elimination

Following oral administration of radiolabeled tasimelteon, 80% of total radioactivity was excreted in urine and approximately 4% in feces, resulting in a mean recovery of 84%. Less than 1% of the dose was excreted in urine as the parent compound.

Volume of Distribution

The apparent oral volume of distribution of tasimelteon at steady state in young healthy subjects is approximately 56 - 126 L.

5.4 Metabolism/Metabolites

Tasimelteon is extensively metabolized. Metabolism of tasimelteon consists primarily of oxidation at multiple sites and oxidative dealkylation resulting in opening of the dihydrofuran ring followed by further oxidation to give a carboxylic acid. CYP1A2 and CYP3A4 are the major isozymes involved in the metabolism of tasimelteon. Phenolic glucuronidation is the major phase II metabolic route.

5.5 Biological Half-Life

The observed mean elimination half-life for tasimelteon is 1.3 0.4 hours.

5.6 Mechanism of Action

Tasimelteon is a selective dual agonist of the melatonin receptors MT1 and MT2.