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

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    Perifosine

    APIs // Active Pharmaceutical Ingredients

    INTERMEDIATES

    PharmaCompass

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    2D Structure
    1. Also known as: 157716-52-4, Krx-0401, 1,1-dimethylpiperidin-1-ium-4-yl octadecyl phosphate, Perifosine (krx-0401), (1,1-dimethylpiperidin-1-ium-4-yl) octadecyl phosphate, Nsc 639966
    Molecular Formula
    C25H52NO4P
    Molecular Weight
    461.7  g/mol
    InChI Key
    SZFPYBIJACMNJV-UHFFFAOYSA-N
    FDA UNII
    2GWV496552
    Perifosine is a novel alkylphospholipid with antiproliferative properties attributed to protein kinase B inhibition.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1,1-dimethylpiperidin-1-ium-4-yl) octadecyl phosphate
    2.1.2 InChI
    InChI=1S/C25H52NO4P/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-24-29-31(27,28)30-25-20-22-26(2,3)23-21-25/h25H,4-24H2,1-3H3
    2.1.3 InChI Key
    SZFPYBIJACMNJV-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCCCCCCCCCCCCCCCCCOP(=O)([O-])OC1CC[N+](CC1)(C)C
    2.2 Other Identifiers
    2.2.1 UNII
    2GWV496552
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. D 21266

    2. D-21266

    3. Octadecyl-(1,1-dimethyl-4-piperidylio)phosphate

    2.3.2 Depositor-Supplied Synonyms

    1. 157716-52-4

    2. Krx-0401

    3. 1,1-dimethylpiperidin-1-ium-4-yl Octadecyl Phosphate

    4. Perifosine (krx-0401)

    5. (1,1-dimethylpiperidin-1-ium-4-yl) Octadecyl Phosphate

    6. Nsc 639966

    7. Perifosine [inn]

    8. D 21266

    9. Nsc-639966

    10. 1,1-dimethylpiperidinium-4-yl Octadecyl Phosphate

    11. Krx 0401

    12. Nsc639966

    13. D-21266

    14. Chebi:67272

    15. 2gwv496552

    16. Ncgc00187909-01

    17. Piperidinium, 4-[[hydroxy(octadecyloxy)phosphinyl]oxy]-1,1-dimethyl-, Inner Salt

    18. 1,1-dimethylpiperidin-1-ium-4-yl Octadecyl Phosphate.

    19. Piperidinium, 4-((hydroxy(octadecyloxy)phosphinyl)oxy)-1,1-dimethyl-, Inner Salt

    20. Nka17

    21. Unii-2gwv496552

    22. Octadecyl-(1,1-dimethyl-4-piperidylio)phosphate

    23. 4-((hydroxy(octadecyloxy)phosphinyl)oxy)-1,1-dimethylpiperidinium Inner Salt

    24. Perifosine [mi]

    25. Dsstox_cid_28872

    26. Dsstox_rid_83141

    27. Perifosine [who-dd]

    28. Dsstox_gsid_48946

    29. Schembl93872

    30. Chembl372764

    31. Gtpl7424

    32. Dtxsid3048946

    33. Bcp00245

    34. Ex-a2229

    35. Yhi-1003

    36. Tox21_113365

    37. Bdbm50431630

    38. Mfcd00927554

    39. Nsc800842

    40. S1037

    41. Piperidinium,1-dimethyl-, Inner Salt

    42. Akos005146344

    43. Ccg-269358

    44. Cs-0209

    45. Db06641

    46. Ex-3388

    47. Gs-3834

    48. Nsc-800842

    49. Ncgc00187909-02

    50. Ncgc00187909-13

    51. Ac-25019

    52. Am808092

    53. Hy-50909

    54. Cas-157716-52-4

    55. Ft-0651459

    56. P2831

    57. A23834

    58. D21266

    59. Octadecyl-(1,1-dimethyl-4-piperidylio) Phosphate

    60. J-500086

    61. Q3411917

    62. Perifosine; Krx-0401; Nsc 639966; D21266

    63. 1,1-dimethylpiperidinium-4-yl Octadecyl Phosphate, Inner Salt

    64. 4-hydroxy-1,1-dimethylpiperidinium Hydroxide, Octadecyl Hydrogen Phosphate, Inner Salt

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 461.7 g/mol
    Molecular Formula C25H52NO4P
    XLogP38.3
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count20
    Exact Mass461.36339614 g/mol
    Monoisotopic Mass461.36339614 g/mol
    Topological Polar Surface Area58.6 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity454
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in solid tumors, multiple myeloma, leukemia (unspecified), lung cancer, and brain cancer.

    5 Pharmacology and Biochemistry
    5.1 Mechanism of Action

    Targeting cellular membranes, perifosine modulates membrane permeability, membrane lipid composition, phospholipid metabolism, and mitogenic signal transduction, resulting in cell differentiation and inhibition of cell growth. This agent also inhibits the anti-apoptotic mitogen-activated protein kinase (MAPK) pathway and modulates the balance between the MAPK and pro-apoptotic stress-activated protein kinase (SAPK/JNK) pathways, thereby inducing apoptosis.

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