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Suvorexant

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Also known as: 1030377-33-3, Mk-4305, Belsomra, Mk4305, Mk 4305, [(7r)-4-(5-chloro-1,3-benzoxazol-2-yl)-7-methyl-1,4-diazepan-1-yl][5-methyl-2-(2h-1,2,3-triazol-2-yl)phenyl]methanone

Molecular Formula

C₂₃H₂₃ClN₆O₂

Molecular Weight

450.9 g/mol

InChI Key

JYTNQNCOQXFQPK-MRXNPFEDSA-N

FDA UNII

081L192FO9

Suvorexant is a selective dual antagonist of orexin receptors OX1R and OX2R that promotes sleep by reducing wakefulness and arousal. It has been approved for the treatment of insomnia.

Suvorexant is an Orexin Receptor Antagonist. The mechanism of action of suvorexant is as an Orexin Receptor Antagonist, and P-Glycoprotein Inhibitor, and Cytochrome P450 3A Inhibitor.

1 2D Structure

Suvorexant

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(7R)-4-(5-chloro-1,3-benzoxazol-2-yl)-7-methyl-1,4-diazepan-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone

2.1.2 InChI

InChI=1S/C23H23ClN6O2/c1-15-3-5-20(30-25-8-9-26-30)18(13-15)22(31)29-12-11-28(10-7-16(29)2)23-27-19-14-17(24)4-6-21(19)32-23/h3-6,8-9,13-14,16H,7,10-12H2,1-2H3/t16-/m1/s1

2.1.3 InChI Key

JYTNQNCOQXFQPK-MRXNPFEDSA-N

2.1.4 Canonical SMILES

CC1CCN(CCN1C(=O)C2=C(C=CC(=C2)C)N3N=CC=N3)C4=NC5=C(O4)C=CC(=C5)Cl

2.1.5 Isomeric SMILES

C[C@@H]1CCN(CCN1C(=O)C2=C(C=CC(=C2)C)N3N=CC=N3)C4=NC5=C(O4)C=CC(=C5)Cl

2.2 Other Identifiers

2.2.1 UNII

081L192FO9

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (4-(5-chloro-1,3-benzoxazol-2-yl)-7-methyl-1,4-diazepan-1-yl)(5-methyl-2-(2h-1,2,3-triazol-2-yl)phenyl)methanone

2. Belsomra

3. Methanone, ((7r)-4-(5-chloro-2-benzoxazolyl)hexahydro-7-methyl-1h-1,4-diazepin-1-yl)(5-methyl-2-(2h-1,2,3-triazol-2-yl)phenyl)-

4. Mk 4305

5. Mk-4305

6. Mk4305

2.3.2 Depositor-Supplied Synonyms

1. 1030377-33-3

2. Mk-4305

3. Belsomra

4. Mk4305

5. Mk 4305

6. [(7r)-4-(5-chloro-1,3-benzoxazol-2-yl)-7-methyl-1,4-diazepan-1-yl][5-methyl-2-(2h-1,2,3-triazol-2-yl)phenyl]methanone

7. Suvorexant (mk-4305)

8. 5-chloro-2-[(5r)-5-methyl-4-[5-methyl-2-(2h-1,2,3-triazol-2-yl)benzoyl]-1,4-diazepan-1-yl]-1,3-benzoxazole

9. Chembl1083659

10. Chebi:82698

11. 081l192fo9

12. ((7r)-4-(5-chloro-1,3-benzoxazol-2-yl)-7-methyl-1,4-diazepan-1-yl)(5-methyl-2-(2h-1,2,3-triazol-2-yl)phenyl)methanone

13. Methanone, ((7r)-4-(5-chloro-2-benzoxazolyl)hexahydro-7-methyl-1h-1,4-diazepin-1-yl)(5-methyl-2-(2h-1,2,3-triazol-2-yl)phenyl)-

14. (r)-(4-(5-chlorobenzo[d]oxazol-2-yl)-7-methyl-1,4-diazepan-1-yl)(5-methyl-2-(2h-1,2,3-triazol-2-yl)phenyl)methanone.

15. [(7r)-4-(5-chloro-1,3-benzoxazol-2-yl)-7-methyl-1,4-diazepan-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone

16. Suvorexant [usan:inn]

17. Dora-analogue

18. Unii-081l192fo9

19. Belsomra (tn)

20. Suv

21. Suvorexant [mi]

22. Suvorexant [inn]

23. Suvorexant [jan]

24. Suvorexant (jan/usan)

25. Suvorexant [usan]

26. Suvorexant; Mk 4305

27. Suvorexant [vandf]

28. Suvorexant [who-dd]

29. Amy337

30. Gtpl2890

31. Schembl1586289

32. Suvorexant [orange Book]

33. Dtxsid90145616

34. Ex-a211

35. Belsomra Component Suvorexant

36. Bdbm50318701

37. Mfcd22377755

38. Zinc49036447

39. Akos022185167

40. Cs-0614

41. Db09034

42. Suvorexant Component Of Belsomra

43. (4-(5-chloro-1,3-benzoxazol-2-yl)-7-methyl-1,4-diazepan-1-yl)(5-methyl-2-(2h-1,2,3-triazol-2-yl)phenyl)methanone

44. Ac-30276

45. As-74879

46. Hy-10807

47. Bcp0726000197

48. Ft-0697203

49. Sw219649-1

50. D10082

51. J-690010

52. Q7650517

53. Cas:1030377-33-3;mk-4305

54. 5-chloro-2-[(5r)-5-methyl-4-[5-methyl-2-(2h-1,2,3-triazol-2-yl)benzoyl]-1,4-diazepan-1-yl]-1,3-benzoxazole Mk 4305

2.4 Create Date

2008-10-20

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₂₃ClN₆O₂
Molecular Weight	450.9 g/mol
XLogP3	4.9
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	450.1571017 g/mol
Monoisotopic Mass	450.1571017 g/mol
Topological Polar Surface Area	80.3 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	664
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
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

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

FDA Label

5 Pharmacology and Biochemistry

5.1 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.)

Sleep Aids, Pharmaceutical

Drugs used to induce SLEEP, prevent SLEEPLESSNESS, or treat SLEEP INITIATION AND MAINTENANCE DISORDERS. (See all compounds classified as Sleep Aids, Pharmaceutical.)

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

SUVOREXANT

5.2.2 FDA UNII

081L192FO9

5.2.3 Pharmacological Classes

Orexin Receptor Antagonist [EPC]; Orexin Receptor Antagonists [MoA]; P-Glycoprotein Inhibitors [MoA]; Cytochrome P450 3A Inhibitors [MoA]

5.3 ATC Code

N - Nervous system

N05 - Psycholeptics

N05C - Hypnotics and sedatives

N05CM - Other hypnotics and sedatives

N05CM19 - Suvorexant

5.4 Absorption, Distribution and Excretion

Absorption

Peak concentrations occur at a median Tmax of 2 hours under fasted conditions. Ingestion of suvorexant with a high-fat meal has no effect on AUC or Cmax, but may delay Tmax by approximately 1.5 hours. Mean absolute bioavailability of 10 mg is 82%.

Route of Elimination

Approximately 66% is eliminated in feces and 23% is eliminated in urine.

Volume of Distribution

Mean volume of distribution is approximately 49 litres.

5.5 Metabolism/Metabolites

Suvorexant is primarily metabolized by cytochrome-P450 3A4 enzyme (CYP3A4) with a minor contribution from CYP2C19. Major circulating metabolites are suvorexant and a hydroxy-suvorexant metabolite, which is not expected to be pharmacologically active. There is potential for drug-drug interactions with drugs that inhibit or induce CYP3A4 activity.

5.6 Biological Half-Life

Mean half life is approximately 12 hours.

5.7 Mechanism of Action

Suvorexant is a dual antagonist of orexin receptors OX1R and OX2R. It exerts its pharmacological effect by inhibiting binding of neuropeptides orexin A and B, also known as hypocretin 1 and 2, that are produced by neurons in the lateral hypothalamus. These neurons control the wake-promoting centers of the brain and are active during wakefulness, especially during motor activities, and stop firing during sleep. By inhibiting the reinforcement of arousal systems, suvorexant use causes a decrease in arousal and wakefulness, rather than having a direct sleep-promoting effect.

API SUPPLIERS

01

Biophore India Pharmaceuticals Pvt...

India

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02

Metrochem API Private Limited

India

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Pharmtech & Ingredients

Exhibiting

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03

Dasami Lab

India

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04

Hangzhou Longshine Bio-Tech

China

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05

Saptagir Laboratories

India

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06

Haoyuan Chemexpress Co.Ltd

China

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07

Hetero Drugs

India

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08

Viatris

U.S.A

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Not Confirmed

09

Alembic Pharmaceuticals Limited

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

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10

DEAFARMA

Italy

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API Reference Price

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1 SPI Pharma

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