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    Chemistry

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    Also known as: 1231929-97-7, Ly2835219, Verzenio, Ly2835219 free base, Ly-2835219, Unii-60uab198hk
    Molecular Formula
    C27H32F2N8
    Molecular Weight
    506.6  g/mol
    InChI Key
    UZWDCWONPYILKI-UHFFFAOYSA-N
    FDA UNII
    60UAB198HK
    Abemaciclib
    Abemaciclib is an orally available cyclin-dependent kinase (CDK) inhibitor that targets the CDK4 (cyclin D1) and CDK6 (cyclin D3) cell cycle pathway, with potential antineoplastic activity. Abemaciclib specifically inhibits CDK4 and 6, thereby inhibiting retinoblastoma (Rb) protein phosphorylation in early G1. Inhibition of Rb phosphorylation prevents CDK-mediated G1-S phase transition, thereby arresting the cell cycle in the G1 phase, suppressing DNA synthesis and inhibiting cancer cell growth. Overexpression of the serine/threonine kinases CDK4/6, as seen in certain types of cancer, causes cell cycle deregulation.
    Abemaciclib is a Kinase Inhibitor. The mechanism of action of abemaciclib is as a Kinase Inhibitor.
    1 2D Structure

    Abemaciclib

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]-5-fluoro-4-(7-fluoro-2-methyl-3-propan-2-ylbenzimidazol-5-yl)pyrimidin-2-amine
    2.1.2 InChI
    InChI=1S/C27H32F2N8/c1-5-35-8-10-36(11-9-35)16-19-6-7-24(30-14-19)33-27-31-15-22(29)25(34-27)20-12-21(28)26-23(13-20)37(17(2)3)18(4)32-26/h6-7,12-15,17H,5,8-11,16H2,1-4H3,(H,30,31,33,34)
    2.1.3 InChI Key
    UZWDCWONPYILKI-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCN1CCN(CC1)CC2=CN=C(C=C2)NC3=NC=C(C(=N3)C4=CC5=C(C(=C4)F)N=C(N5C(C)C)C)F
    2.2 Other Identifiers
    2.2.1 UNII
    60UAB198HK
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5-(4-ethylpiperazin-1-ylmethyl)pyridin-2-yl)-(5-fluoro-4-(7-fluoro-3-isopropyl-2-methyl-3h-benzimidazol-5-yl)pyrimidin-2-yl)amine

    2. 5-(4-ethylpiperazin-1-ylmethyl)pyridin-2-yl)-(5-fluoro-4-(7-fluoro-3-isopropyl-2-methyl-3h-benzoimidazol-5-yl)pyrimidin-2-yl)amine

    3. Abemaciclib Mesylate

    4. Ly-2835219

    5. Ly2385219

    6. Ly2835210

    7. Ly2835219

    8. Verzenio

    2.3.2 Depositor-Supplied Synonyms

    1. 1231929-97-7

    2. Ly2835219

    3. Verzenio

    4. Ly2835219 Free Base

    5. Ly-2835219

    6. Unii-60uab198hk

    7. N-(5-((4-ethylpiperazin-1-yl)methyl)pyridin-2-yl)-5-fluoro-4-(4-fluoro-1-isopropyl-2-methyl-1h-benzo[d]imidazol-6-yl)pyrimidin-2-amine

    8. N-[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]-5-fluoro-4-(7-fluoro-2-methyl-3-propan-2-ylbenzimidazol-5-yl)pyrimidin-2-amine

    9. Abemaciclib (ly2835219)

    10. 60uab198hk

    11. Ly 2835219

    12. Hy-16297a

    13. Cs-1230

    14. 2-pyrimidinamine, N-(5-((4-ethyl-1-piperazinyl)methyl)-2-pyridinyl)-5-fluoro-4-(4-fluoro-2-methyl-1-(1-methylethyl)-1h-benzimidazol-6-yl)

    15. N-{5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl}-5-fluoro-4-(7-fluoro-3-isopropyl-2-methyl-1,3-benzodiazol-5-yl)pyrimidin-2-amine

    16. N-{5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl}-5-fluoro-4-[4-fluoro-2-methyl-1-(propan-2-yl)-1h-benzimidazol-6-yl]pyrimidin-2-amine

    17. Ly2835219 (free Base)

    18. Abemaciclib [usan:inn]

    19. Abemaciclib,ly2835219

    20. Verzenios

    21. Rimidin-2-amine

    22. Verzenio (tn)

    23. 6zv

    24. N-{5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl}-5-fluoro-4-[4-fluoro-2-methyl-1-(propan-2-yl)-1h-benzimidazol-6-yl]py Rimidin-2-amine

    25. Cdk4/6 Dual Inhibitor

    26. Ly2835210

    27. Abemaciclib [mi]

    28. Abemaciclib [inn]

    29. Abemaciclib [jan]

    30. Abemaciclib (jan/usan)

    31. Abemaciclib [usan]

    32. Abemaciclib [who-dd]

    33. Gtpl7382

    34. Schembl2487229

    35. Chembl3301610

    36. Abemaciclib [orange Book]

    37. Dtxsid20673119

    38. Ex-a521

    39. Ly 2835219 (free Base)

    40. Hms3673i05

    41. Bcp13079

    42. Ex-a1588

    43. Bdbm50110183

    44. Mfcd22665744

    45. Nsc768073

    46. Nsc783671

    47. S5716

    48. Zinc72318121

    49. 1231929-97-7, Verzenio,

    50. Akos025404907

    51. Ly2835219 Free Base (abemaciclib)

    52. Ccg-269750

    53. Db12001

    54. Nsc-768073

    55. Nsc-783671

    56. Sb16476

    57. Ncgc00351599-02

    58. Ncgc00351599-06

    59. 5-(4-ethylpiperazin-1-ylmethyl)pyridin-2-yl)-(5-fluoro-4-(7-fluoro-3-isopropyl-2-methyl-3h-benzimidazol-5-yl)pyrimidin-2-yl)amine

    60. 5-(4-ethylpiperazin-1-ylmethyl)pyridin-2-yl)-(5-fluoro-4-(7-fluoro-3-isopropyl-2-methyl-3h-benzoimidazol-5-yl)pyrimidin-2-yl)amine

    61. Ac-30666

    62. As-10230

    63. Da-33422

    64. Ly2835219 Ms Salt, Abemaciclib Ms Salt

    65. Ft-0700134

    66. Ly 2835210

    67. A12989

    68. D10688

    69. J-690083

    70. Q23901483

    71. [5-(4-ethyl-piperazin-1-ylmethyl)-pyridin-2-yl]-[5-fluoro-4-(7-fluoro-3-isopropyl-2-methyl-3h-benzoimidazol-5-yl)-pyrimidin-2-yl]-amine

    72. 2-pyrimidinamine, N-[5-[(4-ethyl-1-piperazinyl)methyl]-2-pyridinyl]-5-fluoro-4-[4-fluoro-2-methyl-1-(1-methylethyl)-1h-benzimidazol-6-yl]-

    73. 2-pyrimidinamine,n-[5-[(4-ethyl-1-piperazinyl)methyl]-2-pyridinyl]-5-fluoro-4-[4-fluoro-2-methyl-1-(1-methylethyl)-1h-benzimidazol-6-yl]-

    74. N-{5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl}-5-fluoro-4-[4-fluoro-2-methyl-1-(propan-2-yl)-1h-benzimidazol-6-yl]py

    2.4 Create Date
    2010-07-06
    3 Chemical and Physical Properties
    Molecular Weight 506.6 g/mol
    Molecular Formula C27H32F2N8
    XLogP33.8
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count7
    Exact Mass506.27179938 g/mol
    Monoisotopic Mass506.27179938 g/mol
    Topological Polar Surface Area75 Ų
    Heavy Atom Count37
    Formal Charge0
    Complexity723
    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 Information
    1 of 1  
    Drug NameVERZENIO
    Active IngredientABEMACICLIB
    CompanyELI LILLY AND CO (Application Number: N208716. Patent: 7855211)

    4.2 Drug Indication

    * Indicated in combination with fulvestrant for the treatment of women with hormone receptor (HR)-positive, human epidermal growth factor receptor 2 (HER2)-negative advanced or metastatic breast cancer with disease progression following endocrine therapy. * Inidicated as monotherapy for the treatment of adult patients with HR-positive, HER2-negative advanced or metastatic breast cancer with disease progression following endocrine therapy and prior chemotherapy in the metastatic setting.

    Early Breast Cancer

    Verzenios in combination with endocrine therapy is indicated for the adjuvant treatment of adult patients with hormone receptor (HR) positive, human epidermal growth factor receptor 2 (HER2) negative, node positive early breast cancer at high risk of recurrence (see section 5. 1).

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

    Advanced or Metastatic Breast Cancer

    Verzenios is indicated for the treatment of women with hormone receptor (HR) positive, human epidermal growth factor receptor 2 (HER2) negative locally advanced or metastatic breast cancer in combination with an aromatase inhibitor or fulvestrant as initial endocrine-based therapy, or in women who have received prior endocrine therapy.

    In pre- or perimenopausal women, the endocrine therapy should be combined with a LHRH agonist.

    Treatment of Ewing sarcoma

    Treatment of breast cancer

    Treatment of high-grade glioma, Treatment of neuroblastoma

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    In combination with fulvestrant, the progression-free survival for patients with HR-positive, HER2-negative breast cancer was 16.4 months compared to 9.3 months for patients taking a placebo with fulvestrant. As a monotherapy, 19.7% of patients taking abemaciclib achieved complete or partial shrinkage of their tumors for a median 8.6 months after treatment. Abemaciclib induces cell cycle arrest and exerts an antitumor activity in human tumor xenograft models. In patient investigations and a healthy volunteer study, abemaciclib is not shown to induce any clinically significant changes in the QTc interval.

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    ABEMACICLIB
    5.2.2 FDA UNII
    60UAB198HK
    5.2.3 Pharmacological Classes
    Kinase Inhibitors [MoA]; Kinase Inhibitor [EPC]
    5.3 ATC Code

    L01EF03

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01E - Protein kinase inhibitors

    L01EF - Cyclin-dependent kinase (cdk) inhibitors

    L01EF03 - Abemaciclib

    5.4 Absorption, Distribution and Excretion

    Absorption

    The plasma concentration of the drug increases in a dose-proportional manner. Following a single oral dose administration of 200 mg abemaciclib, the mean peak plasma concentration (Cmax) of 158 ng/mL is reached after 6 hours. The median time to reach maximum plasma concentration (Tmax) ranges from 4-6 hours following an oral administration of abemaciclib over a range of 50275 mg, but may range up to 24 hours. The absolute bioavailability of the drug is reported to be 45%.

    Route of Elimination

    Following a single oral dose of 150mg radiolabeled abemaciclib, approximately 81% of the total dose was recovered in feces while 3% of the dose was detected in urine. The majority of the drug is exceted as metabolites.

    Volume of Distribution

    The geometric mean systemic volume of distribution is approximately 690.3 L (49% CV).

    Clearance

    The geometric mean hepatic clearance (CL) of abemaciclib in patients was 26.0 L/h (51% CV).

    5.5 Metabolism/Metabolites

    Abemaciclib mainly undergoes hepatic metabolism mediated by CYP3A4. The major metabolite formed is N-desethylabemaciclib (M2), while other metabolites hydroxyabemaciclib (M20), hydroxy-N-desethylabemaciclib (M18), and an oxidative metabolite (M1) are also formed. M2, M18, and M20 are equipotent to abemaciclib and their AUCs accounted for 25%, 13%, and 26% of the total circulating analytes in plasma, respectively.

    5.6 Biological Half-Life

    The mean plasma elimination half-life for abemaciclib in patients was 18.3 hours (72% CV).

    5.7 Mechanism of Action

    Regulation of cell cycle is crucial in maintaining proper cell growth; dysregulated cell cycle signalling pathway is a key component in inducing hyperproliferation of cells and tumor formation in various cancers. G1 to S phase cell cycle progression, or transition through the G1 restriction point (R), is promoted by the retinoblastoma tumor suppressor protein (Rb)-mediated pathway. Activation of Rb-mediated pathway requires the interaction of Cyclin-dependent kinases (CDK) 4 and 6 with D-type cyclins, which drives the formation of active CDK4/CDK6 and subsequent phosphorylation of Rb. Rb is a tumor suppressant protein that inhibits proliferation through binding to and suppressing the activity of the E2F family of transcription factors. However, phosphorylation of Rb relieves suppression of E2F to allow expression of genes required for passage through the restriction point. This leads to increased expression of downstream signalling molecules and activity of protein kinases that promote the cell cycle progression and initiation of DNA replication. Phosphorylation of Rb and other proteins by CDK4/6 additionally leads to transcription of genes involved in cell cycle-independent activities including signal transduction, DNA repair transcriptional control, and mRNA processing. Abemaciclib selectively inhibits CDK4 and CDK6 with low nanomolar potency, inhibits Rb phosphorylation resulting in a G1 arrest and inhibition of proliferation, and its activity is specific for Rb-proficient cells. Unlike other CDK inhibitors such as [DB09073] and [DB11730], abemaciclib exhibits greater selectivity for CDK4 compared to CDK6.

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    MSN Laboratories

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    Antibody Engineering
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    MSN Laboratories

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    Antibody Engineering
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    Abemaciclib IH

    Date of Issue : 2022-09-02

    Valid Till : 2025-05-05

    Written Confirmation Number : WC-0349

    Address of the Firm : MIs. MSN Laboratories Private Limited, Unit-II, sv. No, 50, Kardanur (Village), ...

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    API Reference Price

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    [{"dataSource":"API Export","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1711996200,"product":"ABEMACICLIB","address":"MSN HOUSE, PLOT NO. C-24,","city":"HYDERABAD. AP","supplier":"MSN LABORATORIES","supplierCountry":"INDIA","foreign_port":"AMMAN","customer":"HIKMA PHARMACEUTICALS","customerCountry":"JORDAN","quantity":"0.50","actualQuantity":"0.5","unit":"KGS","unitRateFc":"25000","totalValueFC":"12193.4","currency":"USD","unitRateINR":2036478,"date":"02-Apr-2024","totalValueINR":"1018239","totalValueInUsd":"12193.4","indian_port":"Hyderabad Air","hs_no":"29339990","bill_no":"8837718","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"JORDAN","selfForZScoreResived":"Pharma Grade","supplierPort":"Hyderabad Air","supplierAddress":"MSN HOUSE, PLOT NO. C-24,, HYDERABAD. AP","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1713551400,"product":"ABEMACICLIB","address":"MSN HOUSE, PLOT NO. C-24,","city":"HYDERABAD. AP","supplier":"MSN LABORATORIES","supplierCountry":"INDIA","foreign_port":"SAO PAULO - CONGONHA","customer":"LIBBS FARMACEUTICA","customerCountry":"BRAZIL","quantity":"0.15","actualQuantity":"0.15","unit":"KGS","unitRateFc":"35000","totalValueFC":"5199.2","currency":"USD","unitRateINR":2894500,"date":"20-Apr-2024","totalValueINR":"434175","totalValueInUsd":"5199.2","indian_port":"Hyderabad Air","hs_no":"29339990","bill_no":"9270691","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"BRAZIL","selfForZScoreResived":"Pharma Grade","supplierPort":"Hyderabad Air","supplierAddress":"MSN HOUSE, PLOT NO. C-24,, HYDERABAD. AP","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1716921000,"product":"ABEMACICLIB","address":"MSN HOUSE, PLOT NO. C-24,","city":"HYDERABAD. AP","supplier":"MSN LABORATORIES","supplierCountry":"INDIA","foreign_port":"SAO PAULO - CONGONHA","customer":"LIBBS FARMACEUTICA","customerCountry":"BRAZIL","quantity":"0.15","actualQuantity":"0.15","unit":"KGS","unitRateFc":"35000","totalValueFC":"5205.6","currency":"USD","unitRateINR":2892750,"date":"29-May-2024","totalValueINR":"433912.5","totalValueInUsd":"5205.6","indian_port":"Hyderabad Air","hs_no":"29339990","bill_no":"1256271","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"BRAZIL","selfForZScoreResived":"Pharma Grade","supplierPort":"Hyderabad Air","supplierAddress":"MSN HOUSE, PLOT NO. C-24,, HYDERABAD. AP","customerAddress":""}]
    02-Apr-2024
    29-May-2024
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