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    Chemistry

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    Also known as: 175131-60-9, Milnacipran hydrochloride, (1s-cis)-milnacipran hydrochloride, Fetzima, F 2695 hydrochloride, 101152-94-7
    Molecular Formula
    C15H23ClN2O
    Molecular Weight
    282.81  g/mol
    InChI Key
    XNCDYJFPRPDERF-NQQJLSKUSA-N
    FDA UNII
    371U2ZK31U
    Milnacipran HCl
    The (1S,2R)-isomer of milnacipran that is used for the treatment of MAJOR DEPRESSIVE DISORDER.
    1 2D Structure

    Milnacipran HCl

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1S,2R)-2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropane-1-carboxamide;hydrochloride
    2.1.2 InChI
    InChI=1S/C15H22N2O.ClH/c1-3-17(4-2)14(18)15(10-13(15)11-16)12-8-6-5-7-9-12;/h5-9,13H,3-4,10-11,16H2,1-2H3;1H/t13-,15+;/m0./s1
    2.1.3 InChI Key
    XNCDYJFPRPDERF-NQQJLSKUSA-N
    2.1.4 Canonical SMILES
    CCN(CC)C(=O)C1(CC1CN)C2=CC=CC=C2.Cl
    2.1.5 Isomeric SMILES
    CCN(CC)C(=O)[C@]1(C[C@H]1CN)C2=CC=CC=C2.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    371U2ZK31U
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Fetzima

    2. Levomilnacipran

    2.3.2 Depositor-Supplied Synonyms

    1. 175131-60-9

    2. Milnacipran Hydrochloride

    3. (1s-cis)-milnacipran Hydrochloride

    4. Fetzima

    5. F 2695 Hydrochloride

    6. 101152-94-7

    7. Milnacipran ((1s-cis) Hydrochloride)

    8. Milnacipran (1s-cis) Hydrochloride

    9. Levomilnacipran Hcl

    10. F2695 Hydrochloride

    11. Levomilnacipran Hydrochloride [usan]

    12. F-2695 Hydrochloride

    13. 371u2zk31u

    14. (1s,2r)-2-(aminomethyl)-n,n-diethyl-1-phenylcyclopropane-1-carboxamide;hydrochloride

    15. (1s-cis)-milnacipran Hcl

    16. (1s,2r)-2-(aminomethyl)-n,n-diethyl-1-phenylcyclopropanecarboxamide Hydrochloride

    17. Levomilnacipran Hydrochloride (usan)

    18. Cyclopropanecarboxamide, 2-(aminomethyl)-n,n-diethyl-1-phenyl-, Hydrochloride (1:1), (1s,2r)-

    19. Midalcipran Hydrochloride

    20. Rac-milnacipran Hydrochloride

    21. Joncia

    22. Unii-371u2zk31u

    23. L-milnacipran Hcl

    24. (1s,2r)-milnacipran Hydrochloride

    25. Fetzima (tn)

    26. Tn-912

    27. Schembl1148742

    28. Chembl2105732

    29. Hy-b0168b

    30. Milnacipran Hydrochloride Solution

    31. Dtxsid801026201

    32. Amy10333

    33. Mfcd18433402

    34. S5693

    35. Akos025311514

    36. Ccg-231710

    37. Cs-4972

    38. (1s,2r)-2-(aminomethyl)-n,n-diethyl-1-phenylcyclopropane-1-carboxamide Hydrochloride

    39. As-12868

    40. M2133

    41. Milnacipran Hydrochloride, (1s,2r)-

    42. Levomilnacipran Hydrochloride [who-dd]

    43. A14391

    44. C13985

    45. C73344

    46. D10133

    47. F-2207

    48. 152m947

    49. A899431

    50. Levomilnacipran Hydrochloride [orange Book]

    51. Q27256611

    52. Milnacipran Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

    2.4 Create Date
    2006-07-28
    3 Chemical and Physical Properties
    Molecular Weight 282.81 g/mol
    Molecular Formula C15H23ClN2O
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count5
    Exact Mass282.1498911 g/mol
    Monoisotopic Mass282.1498911 g/mol
    Topological Polar Surface Area46.3 Ų
    Heavy Atom Count19
    Formal Charge0
    Complexity295
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    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 2  
    Drug NameFetzima
    PubMed HealthLevomilnacipran (By mouth)
    Drug ClassesAntidepressant
    Active IngredientLevomilnacipran hydrochloride
    Dosage FormCapsule, extended release
    RouteOral
    Strengtheq 40mg base; eq 80mg base; eq 120mg base; eq 20mg base
    Market StatusPrescription
    CompanyForest Labs

    2 of 2  
    Drug NameFetzima
    PubMed HealthLevomilnacipran (By mouth)
    Drug ClassesAntidepressant
    Active IngredientLevomilnacipran hydrochloride
    Dosage FormCapsule, extended release
    RouteOral
    Strengtheq 40mg base; eq 80mg base; eq 120mg base; eq 20mg base
    Market StatusPrescription
    CompanyForest Labs

    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.)

    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.)

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

    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - EQ ...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - EQ 120MG BASE

    USFDA APPLICATION NUMBER - 204168

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    DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - EQ ...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - EQ 20MG BASE

    USFDA APPLICATION NUMBER - 204168

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    DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - EQ ...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - EQ 40MG BASE

    USFDA APPLICATION NUMBER - 204168

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    DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - EQ ...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - EQ 80MG BASE

    USFDA APPLICATION NUMBER - 204168

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