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    Alvocidib

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: Flavopiridol, 146426-40-6, Alvocidib freebase, L86-8275, L 868275, L-868275
    Molecular Formula
    C21H20ClNO5
    Molecular Weight
    401.8  g/mol
    InChI Key
    BIIVYFLTOXDAOV-YVEFUNNKSA-N
    FDA UNII
    45AD6X575G
    Alvocidib is the free base form of a synthetic N-methylpiperidinyl chlorophenyl flavone compound. As an inhibitor of cyclin-dependent kinase, alvocidib induces cell cycle arrest by preventing phosphorylation of cyclin-dependent kinases (CDKs) and by down-regulating cyclin D1 and D3 expression, resulting in G1 cell cycle arrest and apoptosis. This agent is also a competitive inhibitor of adenosine triphosphate activity.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]chromen-4-one
    2.1.2 InChI
    InChI=1S/C21H20ClNO5/c1-23-7-6-12(17(27)10-23)19-14(24)8-15(25)20-16(26)9-18(28-21(19)20)11-4-2-3-5-13(11)22/h2-5,8-9,12,17,24-25,27H,6-7,10H2,1H3/t12-,17+/m0/s1
    2.1.3 InChI Key
    BIIVYFLTOXDAOV-YVEFUNNKSA-N
    2.1.4 Canonical SMILES
    CN1CCC(C(C1)O)C2=C(C=C(C3=C2OC(=CC3=O)C4=CC=CC=C4Cl)O)O
    2.1.5 Isomeric SMILES
    CN1CC[C@@H]([C@@H](C1)O)C2=C(C=C(C3=C2OC(=CC3=O)C4=CC=CC=C4Cl)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    45AD6X575G
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (-)cis-5,7-dihydroxy-2-(2-chlorophenyl)-8-(4-(3-hydroxy-1-methyl)piperidinyl)-4h-1-benzopyran-4-one

    2. Flavopiridol

    3. Hmr 1275

    4. L 868275

    5. L-868275

    6. L86-8275

    2.3.2 Depositor-Supplied Synonyms

    1. Flavopiridol

    2. 146426-40-6

    3. Alvocidib Freebase

    4. L86-8275

    5. L 868275

    6. L-868275

    7. Flavopiridol (alvocidib)

    8. Hmr-1275

    9. Hmr 1274

    10. 131740-09-5

    11. L 86-8275

    12. 2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3s,4r)-3-hydroxy-1-methylpiperidin-4-yl]-4h-chromen-4-one

    13. 2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3s,4r)-3-hydroxy-1-methylpiperidin-4-yl]chromen-4-one

    14. Chembl428690

    15. 45ad6x575g

    16. 2-(2-chlorophenyl)-5,7-dihydroxy-8-((3s,4r)-3-hydroxy-1-methylpiperidin-4-yl)-4h-chromen-4-one

    17. 2-(2-chloro-phenyl)-5,7-dihydroxy-8-(3-hydroxy-1-methyl-piperidin-4-yl)-4h-benzopyran-4-one

    18. Nsc 649890 Hcl

    19. Mdl-107826a

    20. 2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3s,4r)-3-hydroxy-1-methyl-4-piperidyl]chromen-4-one

    21. Alvocidib [inn]

    22. Flavo

    23. Flavoperidol

    24. 4h-1-benzopyran-4-one, 2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3s,4r)-3-hydroxy-1-methyl-4-piperidinyl]-

    25. Alvocidib [usan]

    26. L868275

    27. Alvocidib [usan:inn]

    28. Alvocidibum

    29. Unii-45ad6x575g

    30. Ccris 9399

    31. 4h-1-benzopyran-4-one, 2-(2-chlorophenyl)-5,7-dihydroxy-8-((3s,4r)-3-hydroxy-1-methyl-4-piperidinyl)-

    32. (-)cis-5,7-dihydroxy-2-(2-chlorophenyl)-8-(4-(3-hydroxy-1-methyl)piperidinyl)-4h-1-benzopyran-4-one

    33. Nsc649890

    34. 1c8k

    35. 1e1y

    36. Alvocidib (usan/inn)

    37. Flavopiridol [mi]

    38. Alvocidib [mart.]

    39. Alvocidib [who-dd]

    40. Schembl3652

    41. Flavopiridol Hcl; Alvocidib

    42. Bdbm5655

    43. Gtpl5680

    44. Chebi:47344

    45. Dtxsid20904970

    46. Ex-a1901

    47. Flavopiridol,alvocidib, Hmr-1275

    48. Hmr-1274

    49. Mfcd20501884

    50. Nsc799330

    51. S1230

    52. Zinc21288966

    53. Am84422

    54. Ccg-268666

    55. Db03496

    56. Nsc-799330

    57. (-)-cis-5,7-dihydroxy-2-(2-chlorophenyl)-8-(4-(3-hydroxy-1-methyl)piperidinyl)-4h-1-benzopyran-4-one

    58. 4h-1-benzopyran-4-one, 2-(2-chlorophenyl)-5,7-dihydroxy-8-((3r,4s)-3-hydroxy-1-methyl-4-piperidinyl)-, Rel-(-)-

    59. 4h-1-benzopyran-4-one, 2-(2-chlorophenyl)-5,7-dihydroxy-8-(3-hydroxy-1-methyl-4-piperidinyl)-, Cis-(-)-

    60. As-74761

    61. Hy-10005

    62. A25160

    63. D09868

    64. J-008219

    65. Q4063441

    66. Brd-k87909389-001-01-2

    67. (-)-cis-2-(2-chlorophenyl)-5,7-dihydroxy-8-(3-hydroxy-1-methylpiperidin-4-yl)-4h-1-benzopyran-4-one

    68. 2-(2-chlorophenyl)-5,7-dihydroxy-8-((3s,4r)-3-hydroxy-1-methylpiperidin-4-yl)-4h-chromen-4-one;alvocidib

    69. 4h-1-benzopyran-4-one, 2-(2-chlorophenyl)-2,3-dihydro-5,7-dihydroxy-8-[(3s,4r)-3-hydroxy-1-methyl-4-piperidinyl]-

    70. 5,7-dihydroxy-2-(2-chlorophenyl)-8-(1-methyl-3beta-hydroxypiperidin-4beta-yl)-4h-1-benzopyran-4-one

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 401.8 g/mol
    Molecular Formula C21H20ClNO5
    XLogP33.3
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count2
    Exact Mass401.1030004 g/mol
    Monoisotopic Mass401.1030004 g/mol
    Topological Polar Surface Area90.2 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity628
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    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 esophageal cancer, leukemia (lymphoid), lung cancer, liver cancer, and lymphoma (unspecified).

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    Protein Kinase Inhibitors

    Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)

    Growth Inhibitors

    Endogenous or exogenous substances which inhibit the normal growth of human and animal cells or micro-organisms, as distinguished from those affecting plant growth (= PLANT GROWTH REGULATORS). (See all compounds classified as Growth Inhibitors.)

    5.2 Metabolism/Metabolites

    Flavopiridol has known human metabolites that include (2S,3S,4S,5R)-6-[2-(2-chlorophenyl)-5-hydroxy-8-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.3 Mechanism of Action

    Inhibits cyclin-dependent kinases, arresting cell division and causing apoptosis in non-small lung cancer cells.