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    bicifadine hydrochloride

    PharmaCompass
    Xls

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    2D Structure
    Also known as: 71195-57-8, 1-(4-methylphenyl)-3-azabicyclo[3.1.0]hexane, 1-(p-tolyl)-3-azabicyclo[3.1.0]hexane, Cl-220075, 5-(p-tolyl)-3-azabicyclo[3.1.0]hexane, Schembl38793
    Molecular Formula
    C12H15N
    Molecular Weight
    173.25  g/mol
    InChI Key
    OFYVIGTWSQPCLF-UHFFFAOYSA-N
    Bicifadine (DOV-220075) is a nonopioid analgesic. It is an inhibitor of both the norepinephrine and serotonin transporters and an NMDA antagonist with a non-narcotic profile. Bicifadine was shown to have potent analgesic activity in vivo and was chosen for further development for the treatment of pain.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-(4-methylphenyl)-3-azabicyclo[3.1.0]hexane
    2.1.2 InChI
    InChI=1S/C12H15N/c1-9-2-4-10(5-3-9)12-6-11(12)7-13-8-12/h2-5,11,13H,6-8H2,1H3
    2.1.3 InChI Key
    OFYVIGTWSQPCLF-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=CC=C(C=C1)C23CC2CNC3
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Bicifadine Hydrochloride

    2.2.2 Depositor-Supplied Synonyms

    1. 71195-57-8

    2. 1-(4-methylphenyl)-3-azabicyclo[3.1.0]hexane

    3. 1-(p-tolyl)-3-azabicyclo[3.1.0]hexane

    4. Cl-220075

    5. 5-(p-tolyl)-3-azabicyclo[3.1.0]hexane

    6. Schembl38793

    7. 3-azabicyclo[3.1.0]hexane, 1-(4-methylphenyl)-

    8. Chembl511099

    9. Dtxsid20867995

    10. Hms3743c09

    11. Mcv-4147

    12. Nih-9542

    13. Bdbm50417944

    14. Akos006271730

    15. At33554

    16. Db04889

    17. Dov-220075

    18. Db-014713

    19. 1-(p-tolyl)-3-azabicyclo[3.1.0]-hexane

    20. Am20041063

    21. Cs-0455133

    22. Ft-0718156

    23. 195b578

    24. A837110

    25. 3-azabicyclo[3.1.0]hexane,1-(4-methylphenyl)-,hydrochloride(1:1)

    2.3 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 173.25 g/mol
    Molecular Formula C12H15N
    XLogP32.1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count1
    Rotatable Bond Count1
    Exact Mass173.120449483 g/mol
    Monoisotopic Mass173.120449483 g/mol
    Topological Polar Surface Area12 Ų
    Heavy Atom Count13
    Formal Charge0
    Complexity205
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count2
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of pain.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Bicifadine is a chemically distinct molecule with a unique profile of pharmacological activity. Its primary pharmacological action is to enhance and prolong the actions of norepinephrine and serotonin by inhibiting the transport proteins that terminate the physiological actions of the two biogenic amines. Bicifadine is not a narcotic and is well-tolerated and, in preclinical studies, has been shown not to act at any opiate receptor. Bicifadine does not exhibit any anti-inflammatory activity and does not inhibit prostaglandin synthetase in vitro.

    5.2 Metabolism/Metabolites

    The primary enzymes responsible for the primary metabolism of bicifadine in humans are MAO-B and CYP2D6.

    5.3 Mechanism of Action

    Preclinical studies and clinical trials indicate that bicifadine's analgesic properties result through the enhancement and prolongation of norepinephrine and serotonin actions, however other actions may be involved.