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Technical details about Duloxetine, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
1. Also known as: 136434-34-9, Duloxetine hcl, Cymbalta, (s)-duloxetine hydrochloride, Ariclaim, Xeristar
Molecular Formula
C18H20ClNOS
Molecular Weight
333.9  g/mol
InChI Key
BFFSMCNJSOPUAY-LMOVPXPDSA-N
FDA UNII
9044SC542W

A thiophene derivative and selective NEUROTRANSMITTER UPTAKE INHIBITOR for SEROTONIN and NORADRENALINE (SNRI). It is an ANTIDEPRESSIVE AGENT and ANXIOLYTIC, and is also used for the treatment of pain in patients with DIABETES MELLITUS and FIBROMYALGIA.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(3S)-N-methyl-3-naphthalen-1-yloxy-3-thiophen-2-ylpropan-1-amine;hydrochloride
2.1.2 InChI
InChI=1S/C18H19NOS.ClH/c1-19-12-11-17(18-10-5-13-21-18)20-16-9-4-7-14-6-2-3-8-15(14)16;/h2-10,13,17,19H,11-12H2,1H3;1H/t17-;/m0./s1
2.1.3 InChI Key
BFFSMCNJSOPUAY-LMOVPXPDSA-N
2.1.4 Canonical SMILES
CNCCC(C1=CC=CS1)OC2=CC=CC3=CC=CC=C32.Cl
2.1.5 Isomeric SMILES
CNCC[C@@H](C1=CC=CS1)OC2=CC=CC3=CC=CC=C32.Cl
2.2 Other Identifiers
2.2.1 UNII
9044SC542W
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cymbalta

2. Duloxetine

3. Duloxetine Ethanedioate (1:1), (+-)-isomer - T353987

4. Duloxetine Hcl

5. Duloxetine, (+)-isomer

6. Hcl, Duloxetine

7. Hydrochloride, Duloxetine

8. Ly 227942

9. Ly 248686

10. Ly-227942

11. Ly-248686

12. Ly227942

13. Ly248686

14. N-methyl-3-(1-naphthalenyloxy)-2-thiophenepropanamine

15. N-methyl-3-(1-naphthalenyloxy)-3-(2-thiophene)propanamide

2.3.2 Depositor-Supplied Synonyms

1. 136434-34-9

2. Duloxetine Hcl

3. Cymbalta

4. (s)-duloxetine Hydrochloride

5. Ariclaim

6. Xeristar

7. (s)-n-methyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amine Hydrochloride

8. Duloxetine Hydrochloride [usan]

9. Duloxetine Mylan

10. Duloxetine (hydrochloride)

11. Ly248686 Hcl

12. Ly-248686 Hcl

13. Nsc-759112

14. Cpd000469136

15. Duloxetine (as Hydrochloride)

16. Chebi:31526

17. (3s)-n-methyl-3-naphthalen-1-yloxy-3-thiophen-2-ylpropan-1-amine;hydrochloride

18. 9044sc542w

19. Yentreve (tn)

20. (+)-(s)-n-methyl-gamma-(1-naphthyloxy)-2-thiophenepropylamine Hydrochloride

21. Dsstox_cid_26443

22. Dsstox_rid_81618

23. Dsstox_gsid_46443

24. Duloxetine Boehringer Ingelheim

25. Methyl[3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propyl]amine Hydrochloride

26. (+)-(s)-n-methyl-.gamma.-(1-naphthyloxy)-2-thiophenepropylamine Hydrochloride

27. (s)-n-methyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amine Hcl

28. Smr000469136

29. Dulane 20

30. Cas-136434-34-9

31. Ncgc00164559-01

32. C18h19nos.hcl

33. Unii-9044sc542w

34. Ly 248686 Hcl

35. Cymbalta (tn)

36. Duloxetina Cloridrato

37. Duloxetine Hydrochlorise

38. Duloxetine Lilly

39. Cloridrato De Duloxetina

40. Clorhidrato De Duloxetina

41. Chlorhydrate De Duloxetine

42. Duloxetine Hcl (cymbalta)

43. Mls001401452

44. Mls006010054

45. (s)-duloxetine (hydrochloride)

46. Duloxetine Hydrochloride- Bio-x

47. Chembl1200328

48. Dtxsid9046443

49. Duloxetine Hydrochloride Solution

50. Duloxetine For System Suitability

51. Hy-b0161a

52. Pharmakon1600-01505387

53. Ly-248686 Hydrochloride

54. Amy12420

55. Duloxetine Hydrochloride (jan/usp)

56. Tox21_112188

57. Ac-924

58. Duloxetine Hydrochloride [mi]

59. Mfcd06407958

60. Nsc744012

61. Nsc759112

62. S2084

63. Duloxetine Hydrochloride [jan]

64. (3s)-n-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propan-1-amine Hydrochloride

65. Akos016340453

66. Tox21_112188_1

67. Ccg-101106

68. Cs-1993

69. Ks-1168

70. Nc00356

71. Nsc 759112

72. Nsc-744012

73. (3s)-n-methyl-3-naphthalen-1-yloxy-3-thiophen-2-ylpropan-1-amine Hydrochloride

74. 2-thiophenepropanamine, N-methyl-gamma-(1-naphthalenyloxy)-, Hydrochloride, (gammas)-

75. 2-thiophenepropanamine, N-methyl-gamma-(1-naphthalenyloxy)-, Hydrochloride, (s)-

76. Duloxetine Hydrochloride [mart.]

77. Duloxetine Hydrochloride [usp-rs]

78. Duloxetine Hydrochloride [who-dd]

79. Ncgc00164559-03

80. (s)-(+)-duloxetine Hydrochloride

81. Bd165546

82. Ly-264453

83. D-170

84. D4223

85. Sw197393-3

86. Duloxetine Hydrochloride [orange Book]

87. (s)-duloxetine Hydrochloride, >=98% (hplc)

88. D01179

89. Duloxetine Hydrochloride [ep Monograph]

90. Duloxetine Hydrochloride [usp Monograph]

91. 434d349

92. Q-102508

93. Duloxetine Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

94. (+)-(s)-n-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propanamine Hydrochloride

95. Duloxetine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

96. (+)-(s)-n-methyl-3-(1-naphthyloxy)- 3-(2-thienyl)propanamine Hydrochloride

97. (3s)-n-methyl-3-(naphthalen-1-yloxy)-3-(2-thienyl)propan-1-amine Hydrochloride

98. (3s)-n-methyl-3-naphthalen-1-yloxy-3-thiophen-2-ylpropan-1-amin Hydrochloride.

99. (gammas)-2-thiophenepropanamine, N-methyl-gamma-(1-naphthalenyloxy)hydrochloride (1:1)

100. (gammas)-n-methyl-gamma-(1-naphthalenyloxy)-2-thiophenepropanamine Hydrochloride

101. (s)-(+)-n-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl) Propanamine Hydrochloride

102. (s)-(+)-n-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine Hydrochloride

103. 2-thiophenepropanamine, N-methyl-.gamma.-(1-naphthalenyloxy)-, Hydrochloride, (s)-

104. Duloxetine For System Suitability, European Pharmacopoeia (ep) Reference Standard

105. Duloxetine Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

106. Duloxetine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 333.9 g/mol
Molecular Formula C18H20ClNOS
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count6
Exact Mass333.0954131 g/mol
Monoisotopic Mass333.0954131 g/mol
Topological Polar Surface Area49.5 Ų
Heavy Atom Count22
Formal Charge0
Complexity312
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameCymbalta
PubMed HealthDuloxetine (By mouth)
Drug ClassesAntidepressant, Central Nervous System Agent, Neuropathic Pain Agent
Drug LabelCymbalta (Duloxetine Delayed-Release Capsules) is a selective serotonin and norepinephrine reuptake inhibitor (SSNRI) for oral administration. Its chemical designation is (+)-( )- -methyl--(1-naphthyloxy)-2-thiophenepropylamine hydrochloride. The e...
Active IngredientDuloxetine hydrochloride
Dosage FormCapsule, delayed rel pellets
Routeoral; Oral
Strengtheq 30mg base; eq 20mg base; eq 60mg base
Market StatusPrescription
CompanyLilly

2 of 4  
Drug NameDuloxetine hydrochloride
Drug LabelCymbalta (Duloxetine Delayed-Release Capsules) is a selective serotonin and norepinephrine reuptake inhibitor (SSNRI) for oral administration. Its chemical designation is (+)-( )- -methyl--(1-naphthyloxy)-2-thiophenepropylamine hydrochloride. The e...
Active IngredientDuloxetine hydrochloride
Dosage FormCapsule, delayed rel pellets; Capsule, delayed release
Routeoral; Oral
Strengtheq 40mg base; 60mg; 30mg; eq 30mg base; eq 20mg base; eq 60mg base; 20mg
Market StatusTentative Approval; Prescription
CompanyWockhardt; Actavis Elizabeth; Breckenridge Pharm; Apotex; Alembic Pharms; Teva Pharms Usa; Aurobindo Pharma; Torrent Pharms; Zydus Pharms Usa; Lupin; Dr Reddys Labs; Sandoz; Sun Pharma Global; Impax Labs

3 of 4  
Drug NameCymbalta
PubMed HealthDuloxetine (By mouth)
Drug ClassesAntidepressant, Central Nervous System Agent, Neuropathic Pain Agent
Drug LabelCymbalta (Duloxetine Delayed-Release Capsules) is a selective serotonin and norepinephrine reuptake inhibitor (SSNRI) for oral administration. Its chemical designation is (+)-( )- -methyl--(1-naphthyloxy)-2-thiophenepropylamine hydrochloride. The e...
Active IngredientDuloxetine hydrochloride
Dosage FormCapsule, delayed rel pellets
Routeoral; Oral
Strengtheq 30mg base; eq 20mg base; eq 60mg base
Market StatusPrescription
CompanyLilly

4 of 4  
Drug NameDuloxetine hydrochloride
Drug LabelCymbalta (Duloxetine Delayed-Release Capsules) is a selective serotonin and norepinephrine reuptake inhibitor (SSNRI) for oral administration. Its chemical designation is (+)-( )- -methyl--(1-naphthyloxy)-2-thiophenepropylamine hydrochloride. The e...
Active IngredientDuloxetine hydrochloride
Dosage FormCapsule, delayed rel pellets; Capsule, delayed release
Routeoral; Oral
Strengtheq 40mg base; 60mg; 30mg; eq 30mg base; eq 20mg base; eq 60mg base; 20mg
Market StatusTentative Approval; Prescription
CompanyWockhardt; Actavis Elizabeth; Breckenridge Pharm; Apotex; Alembic Pharms; Teva Pharms Usa; Aurobindo Pharma; Torrent Pharms; Zydus Pharms Usa; Lupin; Dr Reddys Labs; Sandoz; Sun Pharma Global; Impax Labs

4.2 Drug Indication

- Treatment of major depressive disorder;

- Treatment of diabetic peripheral neuropathic pain;

- Treatment of generalised anxiety disorder;

- Duloxetine Mylan is indicated in adults.


Duloxetine Lilly is indicated in adults for:

- Treatment of major depressive disorder

- Treatment of diabetic peripheral neuropathic pain

- Treatment of generalised anxiety disorder

Duloxetine Lilly is indicated in adults.


Yentreve is indicated for women for the treatment of moderate to severe stress urinary incontinence (SUI).


Treatment of major depressive disorder.

Treatment of diabetic peripheral neuropathic pain.

Treatment of generalised anxiety disorder.

Cymbalta is indicated in adults.


Treatment of diabetic peripheral neuropathic pain.

Ariclaim is indicated in adults.


Treatment of diabetic peripheral neuropathic pain in adults.


Treatment of chronic pain, Treatment of diabetic neuropathic pain, Treatment of generalised anxiety disorder, Treatment of major depressive disorder, Treatment of stress urinary incontinence


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antidepressive Agents

Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)


Analgesics

Compounds capable of relieving pain without the loss of CONSCIOUSNESS. (See all compounds classified as Analgesics.)


Serotonin and Noradrenaline Reuptake Inhibitors

Drugs that selectively block or suppress the plasma membrane transport of SEROTONIN and NORADRENALINE into axon terminals and are used as ANTIDEPRESSIVE AGENTS. (See all compounds classified as Serotonin and Noradrenaline Reuptake Inhibitors.)


Dopamine Agents

Any drugs that are used for their effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons. (See all compounds classified as Dopamine Agents.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Serotonin Uptake Inhibitors [MoA]; Serotonin and Norepinephrine Reuptake Inhibitor [EPC]; Norepinephrine Uptake Inhibitors [MoA]
5.3 ATC Code

N06AX21


N06AX21


N06AX21


N06AX21


N06AX21


N06AX21


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