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    Agomelatine

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

    GLOBAL SALES INFORMATION

    MARKET PLACE

    REF. STANDARDS & IMPURITIES

    ANALYTICAL

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    2D Structure
    Also known as: 138112-76-2, Thymanax, Valdoxan, N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide, N-(2-(7-methoxynaphthalen-1-yl)ethyl)acetamide, S20098
    Molecular Formula
    C15H17NO2
    Molecular Weight
    243.30  g/mol
    InChI Key
    YJYPHIXNFHFHND-UHFFFAOYSA-N
    FDA UNII
    137R1N49AD
    Agomelatine is structurally closely related to melatonin. Agomelatine is a potent agonist at melatonin receptors and an antagonist at serotonin-2C (5-HT2C) receptors, tested in an animal model of depression. Agomelatine was developed in Europe by Servier Laboratories Ltd. and submitted to the European Medicines Agency (EMA) in 2005. The Committee for Medical Products for Human Use (CHMP) recommended refusal of marketing authorization on 27 July 2006. The major concern was that efficacy had not been sufficiently shown. In 2006 Servier sold the rights to develop Agomelatine in the US to Novartis. The development for the US market was discontinued in October 2011. It is currently sold in Australia under the Valdoxan trade name.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide
    2.1.2 InChI
    InChI=1S/C15H17NO2/c1-11(17)16-9-8-13-5-3-4-12-6-7-14(18-2)10-15(12)13/h3-7,10H,8-9H2,1-2H3,(H,16,17)
    2.1.3 InChI Key
    YJYPHIXNFHFHND-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(=O)NCCC1=CC=CC2=C1C=C(C=C2)OC
    2.2 Other Identifiers
    2.2.1 UNII
    137R1N49AD
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Ago 178

    2. Ago-178

    3. Ago178

    4. N-(2-(7-methoxy-1-naphthyl)ethyl)acetamide

    5. S 20098

    6. S-20098

    7. S20098

    8. Thymanax

    9. Valdoxan

    2.3.2 Depositor-Supplied Synonyms

    1. 138112-76-2

    2. Thymanax

    3. Valdoxan

    4. N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide

    5. N-(2-(7-methoxynaphthalen-1-yl)ethyl)acetamide

    6. S20098

    7. S-20098

    8. Agomelatine [inn]

    9. Melitor

    10. Ago-178

    11. S 20098

    12. Acetamide, N-[2-(7-methoxy-1-naphthalenyl)ethyl]-

    13. N-(2-(7-methoxy-1-naphthyl)ethyl)acetamide

    14. N-(2-(7-methoxynaphth-1-yl)ethyl)acetamide

    15. N-(2-(7-methoxy-1-naphthalenyl)ethyl)acetamide

    16. Chembl10878

    17. 137r1n49ad

    18. N-[2-(7-methoxy-1-naphthalenyl)ethyl]acetamide

    19. Agomelatine (inn)

    20. Ncgc00253646-01

    21. N-[2-(7-methoxy-1-naphthyl)ethyl]acetamide

    22. Acetamide, N-(2-(7-methoxy-1-naphthalenyl)ethyl)-

    23. N-[2-(7-methoxy-naphthalen-1-yl)-ethyl]-acetamide

    24. Ago 178

    25. Valdoxan (tn)

    26. Unii-137r1n49ad

    27. Ago178

    28. N-[2-(7-methoxynaphth-1-yl)ethyl]acetamide

    29. Sr-01000944938

    30. Agomelatine [inn:ban]

    31. Ago178c

    32. Agomelatine-[d4]

    33. Awy

    34. Agomelatine- Bio-x

    35. Mfcd00916659

    36. Agomelatine [mi]

    37. Agomelatine [mart.]

    38. Dsstox_cid_31431

    39. Dsstox_rid_97317

    40. Dsstox_gsid_57642

    41. Agomelatine [who-dd]

    42. Gtpl198

    43. Mls006011913

    44. Schembl114476

    45. Agomelatine [ema Epar]

    46. Zinc5608

    47. Dtxsid3057642

    48. Agomelatine, >=98% (hplc)

    49. Chebi:134990

    50. Bcpp000421

    51. Hms3604n09

    52. Hms3648g18

    53. Hms3654b07

    54. Hms3884a07

    55. Bcp02084

    56. Tox21_113772

    57. Bbl029084

    58. Bdbm50035179

    59. Pdsp1_001305

    60. Pdsp1_001784

    61. Pdsp2_001289

    62. Pdsp2_001767

    63. S1243

    64. Stl237728

    65. Akos005145681

    66. Ac-3395

    67. Bcp9000250

    68. Ccg-221950

    69. Cs-0740

    70. Db06594

    71. Ks-1247

    72. Sb19508

    73. Ncgc00253646-10

    74. Ba167079

    75. Hy-17038

    76. Smr002530056

    77. Am20090763

    78. B2262

    79. Cas-138112-76-2

    80. Ft-0657383

    81. Sw219177-1

    82. A19445

    83. D02578

    84. Ab01274769-01

    85. Ab01274769_02

    86. 112a762

    87. L000528

    88. Q395229

    89. Q-102507

    90. Sr-01000944938-1

    91. Sr-01000944938-3

    92. F0001-2383

    93. (4-chlorophenyl)-[(9h-fluoren-9-ylmethoxycarbonylamino)]-aceticacid

    94. N-[2-(7-methoxy-naphthalen-1-yl)-ethyl]-acetamide(agomelatine)

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 243.30 g/mol
    Molecular Formula C15H17NO2
    XLogP32.7
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count4
    Exact Mass243.125928785 g/mol
    Monoisotopic Mass243.125928785 g/mol
    Topological Polar Surface Area38.3 Ų
    Heavy Atom Count18
    Formal Charge0
    Complexity280
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    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

    Agomelatine is indicated to treat major depressive episodes in adults.

    Treatment of major depressive episodes in adults.

    Treatment of major depressive episodes in adults.

    Treatment of major depressive episodes

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Agomelatine resynchronises circadian rhythms in animal models of delayed sleep phase syndrome and other circadian rhythm disruptions. It increases noradrenaline and dopamine release specifically in the frontal cortex and has no influence on the extracellular levels of serotonin. Agomelatine has shown an antidepressant-like effect in animal depression models, (learned helplessness test, despair test, and chronic mild stress) circadian rhythm desynchronisation, and in stress and anxiety models. In humans, agomelatine has positive phase shifting properties; it induces a phase advance of sleep, body temperature decline and melatonin onset. Controlled studies in humans have shown that agomelatine is as effective as the SSRI antidepressants paroxetine and sertraline in the treatment of major depression

    5.2 MeSH Pharmacological Classification

    Hypnotics and Sedatives

    Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. (See all compounds classified as Hypnotics and Sedatives.)

    5.3 ATC Code

    N06AX22

    N06AX22

    N06AX22

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    N - Nervous system

    N06 - Psychoanaleptics

    N06A - Antidepressants

    N06AX - Other antidepressants

    N06AX22 - Agomelatine

    5.4 Absorption, Distribution and Excretion

    Absorption

    Bioavailability is less than 5%.

    5.5 Metabolism/Metabolites

    Hepatic (90% CYP1A2 and 10% CYP2C9).

    5.6 Biological Half-Life

    <2 hours

    5.7 Mechanism of Action

    The novel antidepressant agent, agomelatine, behaves as an agonist at melatonin receptors (MT1 and MT2) and as an antagonist at serotonin (5-HT)(2C) receptors.