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Agomelatine

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ANALYTICAL

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1 BioAnalytical Methods

Synopsis

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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

Agomelatine

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 Formula	C₁₅H₁₇NO₂
Molecular Weight	243.30 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	4
Exact Mass	243.125928785 g/mol
Monoisotopic Mass	243.125928785 g/mol
Topological Polar Surface Area	38.3 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	280
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
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

Agomelatine is indicated to treat 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

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.

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