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20 API Suppliers, 3 USDMF, 1 EU WC, 4 NDC API, 17 Listed Suppliers, $ API Reference Price

20 API Suppliers
3 USDMF
1 EU WC
4 NDC API
17 Listed Suppliers
$ API Reference Price

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28 Drugs in Development

28 Drugs in Development

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14 Intermediates Suppliers

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32 FDF Dossiers, 8 FDA Orange Book, 6 Europe, 4 Canada, 6 Australia, 4 South Africa, 4 Listed Dossiers

32 FDF Dossiers
8 FDA Orange Book
6 Europe
4 Canada
6 Australia
4 South Africa
4 Listed Dossiers

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2 DATA COMPILATION #PharmaFlow
2 STOCK RECAP #PipelineProspector
76 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

1 US Medicaid Prescriptions, 6 Finished Drug Prices, 5 Annual Reports

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1 US Medicaid Prescriptions
6 Finished Drug Prices
5 Annual Reports

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2 APIs

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2 APIs

PATENTS & EXCLUSIVITIES

17 US Patents, 8 US Exclusivities

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17 US Patents
8 US Exclusivities

Porton Abemaciclib

Synopsis

ACTIVE PHARMA INGREDIENTS

20

API Suppliers

3

USDMF

0

CEP/COS

CEP/COS Certifications

0

JDMF

1

EU WC

0

KDMF

4

NDC API

0

VMF

17

Listed Suppliers

API REF. PRICE (USD/KG)

$

$ 24,387

MARKET PLACE

2

API

0

FDF

14INTERMEDIATES

FINISHED DOSAGE FORMULATIONS

32

FDF Dossiers

8

FDA Orange Book

FDA (Orange Book)

6

Europe

4

Canada

6

Australia

4

South Africa

4

Listed Dossiers

28DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

0

EDQM

0

USP

0

JP

0

Others

PATENTS & EXCLUSIVITIES

17

US Patents

8

US Exclusivities

0

Health Canada Patents

DIGITAL CONTENT

2

Data Compilation #PharmaFlow

2

Stock Recap #PipelineProspector

0

Weekly News Recap #Phispers

76

News #PharmaBuzz

GLOBAL SALES INFORMATION

US Medicaid (USD)

474,171,738

Annual Reports (USD Million)

9,189

Finished Drug Prices

123 RELATED EXCIPIENT COMPANIES

193EXCIPIENTS BY APPLICATIONS

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 Formula	C₂₇H₃₂F₂N₈
Molecular Weight	506.6 g/mol
XLogP3	3.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	7
Exact Mass	506.27179938 g/mol
Monoisotopic Mass	506.27179938 g/mol
Topological Polar Surface Area	75 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	723
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 1
Drug Name	VERZENIO
Active Ingredient	ABEMACICLIB
Company	ELI 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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