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    Duloxetine

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

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    2D Structure
    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