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MolPort-001-684-664

MolPort-001-684-664

Synopsis, Chemistry

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2 Drug(s) in Development

2 Drug(s) in Development

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8 US Patents

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USA (Orange Book)

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Also known as: 25332-39-2, Trazodone hcl, Desyrel, Bimaran, Molipaxin, Thombran

Molecular Formula

C₁₉H₂₃Cl₂N₅O

Molecular Weight

408.3 g/mol

InChI Key

OHHDIOKRWWOXMT-UHFFFAOYSA-N

FDA UNII

6E8ZO8LRNM

A serotonin uptake inhibitor that is used as an antidepressive agent. It has been shown to be effective in patients with major depressive disorders and other subsets of depressive disorders. It is generally more useful in depressive disorders associated with insomnia and anxiety. This drug does not aggravate psychotic symptoms in patients with schizophrenia or schizoaffective disorders. (From AMA Drug Evaluations Annual, 1994, p309)

1 2D Structure

MolPort-001-684-664

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one;hydrochloride

2.1.2 InChI

InChI=1S/C19H22ClN5O.ClH/c20-16-5-3-6-17(15-16)23-13-11-22(12-14-23)8-4-10-25-19(26)24-9-2-1-7-18(24)21-25;/h1-3,5-7,9,15H,4,8,10-14H2;1H

2.1.3 InChI Key

OHHDIOKRWWOXMT-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CN(CCN1CCCN2C(=O)N3C=CC=CC3=N2)C4=CC(=CC=C4)Cl.Cl

2.2 Other Identifiers

2.2.1 UNII

6E8ZO8LRNM

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Af 1161

2. Af-1161

3. Af1161

4. Apo Trazodone

5. Apo-trazodone

6. Deprax

7. Desyrel

8. Gen Trazodone

9. Gen-trazodone

10. Molipaxin

11. Novo Trazodone

12. Novo-trazodone

13. Nu Trazodone

14. Nu-trazodone

15. Pms Trazodone

16. Pms-trazodone

17. Ratio Trazodone

18. Ratio-trazodone

19. Ratiotrazodone

20. Thombran

21. Tradozone

22. Trazodon Hexal

23. Trazodon Neuraxpharm

24. Trazodon-neuraxpharm

25. Trazodone

26. Trazodonneuraxpharm

27. Trazon

28. Trittico

2.3.2 Depositor-Supplied Synonyms

1. 25332-39-2

2. Trazodone Hcl

3. Desyrel

4. Bimaran

5. Molipaxin

6. Thombran

7. Trazodone (hydrochloride)

8. Af-1161

9. Trialodine

10. Kb-831

11. Oleptro

12. 19666-36-5

13. 6e8zo8lrnm

14. 2-(3-(4-(3-chlorophenyl)piperazin-1-yl)propyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2h)-one Hydrochloride

15. Nsc-292811

16. Af-1161 (free Base)

17. 2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Hydrochloride

18. 2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one;hydrochloride

19. Mls000069698

20. Chebi:9655

21. 1,2,4-triazolo[4,3-a]pyridin-3(2h)-one,2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-,hydrochloride (1:1)

22. 2-(3-(4-(m-chlorophenyl)-1-piperazinyl)propyl)-s-triazolo(4,3-a)pyridin-3(2h)-one Monohydrochloride

23. Trazodone Hydrochloride (desyrel)

24. 1,2,4-triazolo(4,3-a)pyridin-3(2h)-one, 2-(3-(4-(3-chlorophenyl)-1-piperazinyl)propyl)-, Monohydrochloride

25. Devidon

26. Pragmazone

27. Smr000058520

28. Tombran

29. Tritico

30. Triticum

31. Azona

32. 25332-39-2 (hcl)

33. Apo-trazodone

34. Dsstox_cid_24626

35. Dsstox_rid_80361

36. Dsstox_gsid_44626

37. 2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-1,2,4-triazolo[4,3-a]pyridin-3(2h)-one Hydrochloride

38. Desyrel Dividose

39. 2-(3-(4-(3-chlorophenyl)piperazin-1-yl)propyl)-1,2,4-triazolo(4,3-a)pyridin-3(2h)-one Hydrochloride

40. 2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-2h,3h-[1,2,4]triazolo[4,3-a]pyridin-3-one Hydrochloride

41. Sr-01000000190

42. Ncgc00016035-02

43. Einecs 246-855-5

44. Unii-6e8zo8lrnm

45. Cas-25332-39-2

46. Nsc 292811

47. Af 1161

48. Trazodone, Hcl

49. 2-[3-[4-(m-chlorophenyl)-1-piperazinyl]propyl]-s-triazolo[4,3-a]pyridin-3(2h)-one Monohydrochloride

50. Prestwick_478

51. Desyrel (tn)

52. Einecs 243-216-2

53. Trazodone Hydrochloride [usan:usp:jan]

54. 2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-[1,2,4]triazolo[4,5-a]pyridin-3-one

55. Opera_id_850

56. Schembl61754

57. 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-1,2,4-triazolo[4,3-a]pyridin-3(2h)-one Hydrochloride

58. Mls000758230

59. Mls001148260

60. Mls001424009

61. Spectrum1503121

62. Chembl1200798

63. Dtxsid8044626

64. Hms1568l06

65. Hms1922g09

66. Pharmakon1600-01503121

67. Trazodone Hydrochloride (jan/usp)

68. Bcp04922

69. Hy-b0478

70. Tox21_110286

71. Tox21_302685

72. Tox21_501159

73. Trazodone Hydrochloride [mi]

74. Ccg-40299

75. Nsc292811

76. Nsc758393

77. Trazodone Hydrochloride [jan]

78. Trazodone Hydrochloride [hsdb]

79. Trazodone Hydrochloride [usan]

80. Akos015897762

81. Tox21_110286_1

82. Ac-6779

83. Ks-5100

84. Lp01159

85. Nc00046

86. Nsc-758393

87. Trazodone Hydrochloride [mart.]

88. Trazodone Hydrochloride [vandf]

89. Trazodone Hydrochloride [usp-rs]

90. Trazodone Hydrochloride [who-dd]

91. Trazodone Hydrochloride Impurity Standard

92. Ncgc00016035-13

93. Ncgc00094420-01

94. Ncgc00094420-02

95. Ncgc00094420-03

96. Ncgc00094420-04

97. Ncgc00256807-01

98. Ncgc00261844-01

99. 2-(3-(4-(3-chlorophenyl)piperazin-1-y)propyl)-1,2,4-triazolo(4,3-a)pyridine-3(2h)-one Hydrochloride

100. S-triazolo(4,3-a)pyridin-3(2h)-one, 2-(3-(4-(m-chlorophenyl)-1-piperazinyl)propyl)-, Monohydrochloride

101. Eu-0101159

102. Ft-0659024

103. Ft-0675364

104. S2582

105. Trazodone Hydrochloride [orange Book]

106. D00820

107. D97808

108. T 6154

109. Trazodone Hydrochloride [usp Monograph]

110. Trazodone Hydrochloride, >=99% (hplc), Powder

111. 332t392

112. A813950

113. A817789

114. A924854

115. 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-

116. J-015941

117. Sr-01000000190-2

118. Sr-01000000190-8

119. Wln: T56 Anvnnj C3- At6n Dntj Dr Cg &gh

120. Q27108459

121. 1,2,4-triazolo[4,3-a]pyridin-3(2h)-one Hydrochloride

122. Z1550675462

123. Trazodone Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

124. Trazodone Hydrochloride, United States Pharmacopeia (usp) Reference Standard

125. S-triazolo[4, 2-[3-[4-(m-chlorophenyl)-1-piperazinyl]propyl]-, Monohydrochloride

126. S-trizolo[4, 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-, Hydrochloride

127. 1,2,4-triazolo[4,3-a]pyridin-3(2h)-one, 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-, Hydrochloride (1:1)

128. 1,4-triazolo[4,3-a]pyridin-3(2h)-one, 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-, Monohydrochloride

129. 2-(3-(4-(3-chlorophenyl)piperazin-1-yl)propyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2h)-onehydrochloride

130. 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Hydrochloride

131. 2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one;hydron;chloride

132. 2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}[1,2,4]triazolo[4,3-a]pyridin-3(2h)-one Hydrochloride

133. Trazodone Hydrochloride Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₃Cl₂N₅O
Molecular Weight	408.3 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Exact Mass	407.1279658 g/mol
Monoisotopic Mass	407.1279658 g/mol
Topological Polar Surface Area	42.4 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	611
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	2

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Oleptro
PubMed Health	Trazodone (By mouth)
Drug Classes	Antidepressant
Drug Label	Oleptro (trazodone hydrochloride) is a triazolopyridine. It is a white, odorless crystalline powder which is freely soluble in water.Chemical Name: 2-[3-[4-(m-Chlorophenyl)-1-piperazinyl]propyl]-s-triazolo[4,3-a]pyridin-3(2H)-one monohydrochloride St...
Active Ingredient	Trazodone hydrochloride
Dosage Form	Tablet, extended release
Route	Oral
Strength	150mg; 300mg
Market Status	Prescription
Company	Angelini Pharma

2 of 4
Drug Name	Trazodone hydrochloride
Drug Label	Trazodone HCl is an antidepressant chemically unrelated to tricyclic, tetracyclic, or other known antidepressant agents. Trazodone HCl is a triazolopyridine derivative designated as 2-[3-[4-(m-Chlorophenyl)-1-piperazinyl]propyl]s-triazolo[4,3-a]-pyri...
Active Ingredient	Trazodone hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	150mg; 300mg; 100mg; 50mg
Market Status	Prescription
Company	Mylan Pharms; Apotex; Teva Pharms Usa; Torrent Pharms; Mutual Pharm; Vintage; Alvogen; Pliva

3 of 4
Drug Name	Oleptro
PubMed Health	Trazodone (By mouth)
Drug Classes	Antidepressant
Drug Label	Oleptro (trazodone hydrochloride) is a triazolopyridine. It is a white, odorless crystalline powder which is freely soluble in water.Chemical Name: 2-[3-[4-(m-Chlorophenyl)-1-piperazinyl]propyl]-s-triazolo[4,3-a]pyridin-3(2H)-one monohydrochloride St...
Active Ingredient	Trazodone hydrochloride
Dosage Form	Tablet, extended release
Route	Oral
Strength	150mg; 300mg
Market Status	Prescription
Company	Angelini Pharma

4 of 4
Drug Name	Trazodone hydrochloride
Drug Label	Trazodone HCl is an antidepressant chemically unrelated to tricyclic, tetracyclic, or other known antidepressant agents. Trazodone HCl is a triazolopyridine derivative designated as 2-[3-[4-(m-Chlorophenyl)-1-piperazinyl]propyl]s-triazolo[4,3-a]-pyri...
Active Ingredient	Trazodone hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	150mg; 300mg; 100mg; 50mg
Market Status	Prescription
Company	Mylan Pharms; Apotex; Teva Pharms Usa; Torrent Pharms; Mutual Pharm; Vintage; Alvogen; Pliva

4.2 Drug Indication

Treatment of insomnia

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anti-Anxiety Agents

Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here. (See all compounds classified as Anti-Anxiety Agents.)

Antidepressive Agents, Second-Generation

A structurally and mechanistically diverse group of drugs that are not tricyclics or monoamine oxidase inhibitors. The most clinically important appear to act selectively on serotonergic systems, especially by inhibiting serotonin reuptake. (See all compounds classified as Antidepressive Agents, Second-Generation.)

Selective Serotonin Reuptake Inhibitors

Compounds that specifically inhibit the reuptake of serotonin in the brain. (See all compounds classified as Selective Serotonin Reuptake Inhibitors.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Serotonin Reuptake Inhibitor [EPC]