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    Chemistry

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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
    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 Weight 450.9 g/mol
    Molecular Formula C23H23ClN6O2
    XLogP34.9
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count3
    Exact Mass450.1571017 g/mol
    Monoisotopic Mass450.1571017 g/mol
    Topological Polar Surface Area80.3 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity664
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.

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