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    Chemistry

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    Also known as: 571190-30-2, Pd-0332991, Ibrance, Pd0332991, Pd 0332991, Palbociclib free base
    Molecular Formula
    C24H29N7O2
    Molecular Weight
    447.5  g/mol
    InChI Key
    AHJRHEGDXFFMBM-UHFFFAOYSA-N
    FDA UNII
    G9ZF61LE7G
    Palbociclib
    Palbociclib is an orally available cyclin-dependent kinase (CDK) inhibitor with potential antineoplastic activity. Palbociclib selectively inhibits cyclin-dependent kinase 4 (CDK4) and 6 (CDK6), thereby inhibiting retinoblastoma (Rb) protein phosphorylation early in the G1 phase leading to cell cycle arrest. This suppresses DNA replication and decreases tumor cell proliferation. CDK4 and 6 are serine/threonine kinases that are upregulated in many tumor cell types and play a key role in the regulation of cell cycle progression.
    Palbociclib is a Kinase Inhibitor. The mechanism of action of palbociclib is as a Kinase Inhibitor, and Cytochrome P450 3A Inhibitor.
    1 2D Structure

    Palbociclib

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    6-acetyl-8-cyclopentyl-5-methyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one
    2.1.2 InChI
    InChI=1S/C24H29N7O2/c1-15-19-14-27-24(28-20-8-7-18(13-26-20)30-11-9-25-10-12-30)29-22(19)31(17-5-3-4-6-17)23(33)21(15)16(2)32/h7-8,13-14,17,25H,3-6,9-12H2,1-2H3,(H,26,27,28,29)
    2.1.3 InChI Key
    AHJRHEGDXFFMBM-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=C(C(=O)N(C2=NC(=NC=C12)NC3=NC=C(C=C3)N4CCNCC4)C5CCCC5)C(=O)C
    2.2 Other Identifiers
    2.2.1 UNII
    G9ZF61LE7G
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 6-acetyl-8-cyclopentyl-5-methyl-2-(5-piperazin-1-ylpyridin-2-ylamino)-8h-pyrido(2,3-d)pyrimidin-7-one

    2. Ibrance

    3. Pd 0332991

    4. Pd-0332991

    5. Pd0332991

    2.3.2 Depositor-Supplied Synonyms

    1. 571190-30-2

    2. Pd-0332991

    3. Ibrance

    4. Pd0332991

    5. Pd 0332991

    6. Palbociclib Free Base

    7. Unii-g9zf61le7g

    8. 6-acetyl-8-cyclopentyl-5-methyl-2-((5-(piperazin-1-yl)pyridin-2-yl)amino)pyrido[2,3-d]pyrimidin-7(8h)-one

    9. Pd-332991

    10. 571190-30-2 (free Base)

    11. Mfcd11840850

    12. 6-acetyl-8-cyclopentyl-5-methyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7(8h)-one

    13. 6-acetyl-8-cyclopentyl-5-methyl-2-[[5-(piperazin-1-yl)pyridin-2-yl]amino]-8h-pyrido[2,3-d]pyrimidin-7-one

    14. G9zf61le7g

    15. Palbociclib(pd0332991)

    16. Pd 332991

    17. 6-acetyl-8-cyclopentyl-5-methyl-2-(5-piperazin-1-ylpyridin-2-ylamino)-8h-pyrido(2,3-d)pyrimidin-7-one

    18. Chebi:85993

    19. 6-acetyl-8-cyclopentyl-5-methyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one

    20. Lqq

    21. 2euf

    22. 6-acetyl-8-cyclopentyl-5-methyl-2-{[5-(piperazin-1-yl)pyridin-2-yl]amino}pyrido[2,3-d]pyrimidin-7(8h)-one

    23. Pyrido(2,3-d)pyrimidin-7(8h)-one, 6-acetyl-8-cyclopentyl-5-methyl-2-((5-(1-piperazinyl)-2-pyridinyl)amino)-

    24. Palbociclib [usan]

    25. 571190-30-2 Pound Not827022-32-2

    26. Palbociclib [usan:inn]

    27. [d8]-palbociclib

    28. 6-acetyl-8-cyclopentyl-5-methyl-2-((5-(piperazin-1-yl)pyridin-2-yl)amino)-8h-pyrido(2,3-d)pyrimidin-7-one

    29. Ibrance (tn)

    30. Palbociclib- Bio-x

    31. Kinome_3823

    32. Kinome_3824

    33. Palbociclib [mi]

    34. 6-acetyl-8-cyclopentyl-5-methyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8h-pyrido[2,3-d]pyrimidin-7-one Hydrochloride

    35. Palbociclib [inn]

    36. Palbociclib [jan]

    37. Palbociclib (jan/usan)

    38. Palbociclib [who-dd]

    39. Schembl462630

    40. Bdbm6309

    41. Chembl189963

    42. Gtpl7380

    43. Pd 0332991 (palbociclib)

    44. Dtxsid40972590

    45. Ex-a408

    46. Palbociclib [orange Book]

    47. 2euf; Pd 0332991

    48. Otava-bb 1115529

    49. Bcpp000125

    50. Hms3265m09

    51. Hms3265m10

    52. Hms3265n09

    53. Hms3265n10

    54. Hms3744g13

    55. Amy14886

    56. Bcp09274

    57. Bcp18381

    58. Zinc3938686

    59. Nsc758247

    60. Nsc772256

    61. Nsc800815

    62. S4482

    63. Akos022205241

    64. Bcp9001058

    65. Db09073

    66. Nsc-758247

    67. Nsc-772256

    68. Nsc-800815

    69. Sb40426

    70. Pyrido-[2,3-d]-pyrimidin-7-one 43

    71. Ncgc00263129-01

    72. Ncgc00263129-08

    73. Ncgc00263129-21

    74. Ncgc00263129-22

    75. Ac-25485

    76. As-17016

    77. Bp166224

    78. Hy-50767

    79. Sy026143

    80. Ft-0697059

    81. A14427

    82. D10372

    83. 190p302

    84. Pd 0332991,pd0332991

    85. Pd-0332991, Pd0332991

    86. Brd-k51313569-001-01-1

    87. P-0332991

    88. Q15269707

    89. 6-acetyl-8-cyclopentyl-5-methyl-2-((5-(piperazin-1-yl)pyridin-2-yl)amino(pyrido(2,3-d)pyrimidin-7(8h)-one

    90. 6-acetyl-8-cyclopentyl-5-methyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8h-pyrido[2,3-d]pyrimidin-7-one

    91. 6-acetyl-8-cyclopentyl-5-methyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[6,5-d]pyrimidin-7-one

    92. 6-acetyl-8-cyclopentyl-5-methyl-2-[[5-(1-piperazinyl)-2-pyridyl]amino]pyrido[2,3-d]pyrimidin-7(8h)-one

    93. 6-acetyl-8-cyclopentyl-5-methyl-2-[[5-(piperazin-1-yl)-pyridin-2-yl]amino]-8h-pyrido[2,3-d]pyrimidin-7-one

    94. 8-cyclopentyl-6-acetyl-5-methyl-2-{[5-(piperazin-1-yl)pyridin-2-yl]amino}-7h,8h-pyrido[2,3-d]pyrimidin-7-one

    2.4 Create Date
    2006-01-30
    3 Chemical and Physical Properties
    Molecular Weight 447.5 g/mol
    Molecular Formula C24H29N7O2
    XLogP31.8
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count5
    Exact Mass447.23827319 g/mol
    Monoisotopic Mass447.23827319 g/mol
    Topological Polar Surface Area103 Ų
    Heavy Atom Count33
    Formal Charge0
    Complexity775
    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

    Palbociclib is indicated in combination with [letrozole] as initial endocrine-based therapy for the treatment of human epidermal growth factor receptor type 2 (HER2)-negative and hormone receptor(HR)-positive tumors in adult patients with advanced/metastatic breast cancer. It is as well approved in combination with [fulvestrant] in patients with disease progression with prior endocrine therapy. In the official labeling, the use of palbociclib should be accompanied with either an aromatase inhibition, no restricted to letrozole, as initial endocrine-based therapy in postmenopausal women or in man. The breast cancer starts as a group of cancer cells that grow into and destroy the nearby breast tissue. This growth can spread into other parts of the body which is called metastasis. According to the location of the cancer cells, it can be categorized in ductal carcinoma and lobular carcinoma. However, other types of breast cancer include inflammatory breast cancer, Paget disease of the breast, triple negative breast cancer non-Hodgkin lymphoma and soft tissue sarcoma. In males, breast cancer is usually treated as the cases of postmenopausal women and almost all the cases are ductal carcinoma.

    FDA Label

    Ibrance is indicated for the treatment of hormone receptor (HR) positive, human epidermal growth factor receptor 2 (HER2) negative locally advanced or metastatic breast cancer :

    - in combination with an aromatase inhibitor;

    - in combination with fulvestrant in women who have received prior endocrine therapy.

    In pre- or perimenopausal women, the endocrine therapy should be combined with a luteinizing hormone releasing hormone (LHRH) agonist.

    Treatment of breast malignant neoplasms

    Treatment of Ewing sarcoma

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Due to its mechanism of action, palbociclib inhibits cell growth and suppresses DNA replication in retinoblastoma tumor suppressor gene (RB) proficient cancer cells. As expected, these RB cells present a significant increase in the proportion of cells in G1 state and the presence of palbociclib produces effective dephosphorylation of RB, reduce proliferation and induce senescence causing cell-cycle arrest. In vitro studies showed the potential for palbociclib to reduce cellular proliferation of estrogen receptor-positive breast cancer cell lines through the inhibition of the cell-cycle progression from G1 to S phase. In this study, it was demonstrated that the sensitivity of the cells significantly increased with the expression of _RB1_ and _CCND1_ and low expression of _CDKN2A_. As well, palbociclib, combined with antiestrogens, enhanced _in vivo_ antitumor activity in estrogen receptor-positive breast cancer mouse models. In clinical trials, palbociclib, in combination with letrozole, was shown to significantly increase the progression-free survival (PFS) in patients with metastatic breast cancer without prior endocrine treatment. In the results, the PFS increased from 4.5 to 9.5 months with an overall response rate (ORR) of 24.6%.

    5.2 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.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    PALBOCICLIB
    5.3.2 FDA UNII
    G9ZF61LE7G
    5.3.3 Pharmacological Classes
    Kinase Inhibitor [EPC]; Kinase Inhibitors [MoA]; Cytochrome P450 3A Inhibitors [MoA]
    5.4 ATC Code

    L01XE33

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01E - Protein kinase inhibitors

    L01EF - Cyclin-dependent kinase (cdk) inhibitors

    L01EF01 - Palbociclib

    5.5 Absorption, Distribution and Excretion

    Absorption

    Palbociclib presents a linear pharmacokinetic profile and its peak plasma concentration was observed 6-12 hours after oral administration. The oral bioavailability is reported to be of 46% with a steady-state reached after 8 days and a median accumulation ratio of 2.4. The absorption of palbociclib is significantly reduced under fasting conditions and hence, food intake is recommended when this drug is administered.

    Route of Elimination

    The main route of elimination of palbociclib is through feces after hepatic metabolism while renal clearance seems to play a minor role accounting only for 17.5% of the eliminated dose.

    Volume of Distribution

    The mean apparent distribution of palbociclib is 2583 L which suggests that palbociclib penetrates extensively into peripheral tissues.

    Clearance

    The mean apparent oral clearance of palbociclib is of 63.1 L/h.

    5.6 Metabolism/Metabolites

    Palbociclib is mainly hepatically transformed. the metabolism is mainly performed by the activities of the cytochrome P450 isoenzyme 3A and the sulfotransferase 2A1. The metabolism of palbociclib is represented mainly by reactions of oxidation and sulfonation followed by acylation and glucuronidation as minor reactions. After its metabolism, palbociclib forms mainly inactive glucuronide and sulfamic acid conjugates. The major circulating metabolite, accounting for 1.5% of the dose in excreta is is the glucuronide conjugate.

    5.7 Biological Half-Life

    The mean plasma elimination half-life of palbociclib is 29 hours.

    5.8 Mechanism of Action

    Palbociclib is a cyclin-dependent kinase 4/6 (CDK4/6) inhibitor that acts by binding to the ATP pocket with an IC50 in the range of 9-15 nmol/L. It is important to consider that it presents low to absent activity against other kinases. The CDK4/6 kinase is involved, with coregulatory partner cyclin D, in the G1-S transition. Hence, inhibition of this step prevents cell cycle progression in cells in whose this pathway is functioning. This step includes the pathways of the phosphorylation of retinoblastoma protein and the E2F family of transcription factors.

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    09-Jan-2021
    19-Nov-2024
    KGS
    overview
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    Average Price (USD/KGS)

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    Total Quantity (KGS)

    Total Value (USD)

    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

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    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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