Abemaciclib

ChemicalBook > CAS DataBase List > Abemaciclib

Product Name: Abemaciclib
CAS No.: 1231929-97-7
Chemical Name: Abemaciclib
Synonyms: N-[5-[(4-Ethyl-1-piperazinyl)methyl]-2-pyridinyl]-5-fluoro-4-[4-fluoro-2-methyl-1-(1-methylethyl)-1H-benzimidazol-6-yl]-2-pyrimidinamine;Abemaciclib (LY2835219);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;CS-814;abecilee;Abemaciclib;Abemaciclib D7;Abemaciclib D10;ABEMACICLIB BASE;Abemaciclib, >=98%
CBNumber: CB72624906
Molecular Formula: C27H32F2N8
Formula Weight: 506.59
MOL File: 1231929-97-7.mol

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Abemaciclib Property

Boiling point:: 689.3±65.0 °C(Predicted)
Density: 1.32±0.1 g/cm3(Predicted)
storage temp.: 4°C, protect from light
solubility: insoluble in H2O; ≥4.83 mg/mL in DMSO with gentle warming and ultrasonic; ≥6.34 mg/mL in EtOH with gentle warming
form: solid
pka: 7.69±0.10(Predicted)
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)
InChIKey: UZWDCWONPYILKI-UHFFFAOYSA-N
SMILES: C1(NC2=NC=C(CN3CCN(CC)CC3)C=C2)=NC=C(F)C(C2C=C3N(C(C)C)C(C)=NC3=C(F)C=2)=N1

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H360May damage fertility or the unborn child

H373May cause damage to organs through prolonged or repeated exposure

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P314Get medical advice/attention if you feel unwell.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 21560
Product name: LY2835219
Purity: ≥98%
Packaging: 1mg
Price: $37
Updated: 2024/03/01

Cayman Chemical

Product number: 21560
Product name: LY2835219
Purity: ≥98%
Packaging: 5mg
Price: $142
Updated: 2024/03/01

Cayman Chemical

Product number: 21560
Product name: LY2835219
Purity: ≥98%
Packaging: 10mg
Price: $231
Updated: 2024/03/01

Cayman Chemical

Product number: 21560
Product name: LY2835219
Purity: ≥98%
Packaging: 25mg
Price: $530
Updated: 2024/03/01

TRC

Product number: A115153
Product name: Abemaciclib
Packaging: 50mg
Price: $95
Updated: 2021/12/16

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Abemaciclib Chemical Properties,Usage,Production

Uses

Abemaciclib is a potent and selective inhibitor of cyclin-dependent kinases, CDK4 and CDK6, as a method to inhibit the proliferation of cancer cells.

Indications

Abemaciclib is used to treat breast cancer that is estrogen receptor-positive (ER-positive) and HER2-negative. It can be taken by both men and women. Patients may be offered abemaciclib if they have:
Early primary breast cancer that the treatment team thinks has a higher risk of coming back (recurrence). Abemaciclib may be provided as an adjuvant treatment, meaning a treatment given after initial treatment, such as surgery;
Breast cancer that has spread to the tissues and lymph nodes around the chest, neck, and under the breastbone (locally advanced breast cancer);
Breast cancer has spread to other parts of the body, such as the bones, lungs, liver, or brain (secondary breast cancer).

Biological Activity

ly2835219 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. cdk4/6 dual inhibitor ly2835219 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.

Biochem/physiol Actions

LY2835219 (abemaciclib) was identified via compound and biochemical screening by scientists at Eli Lilly and Company Research Laboratories and selected for its biological activity and highly selective inhibition of the complexes CDK4/ cyclin D1 (IC50 =2 nmol/L) and CDK6/cyclin D1 (IC50 =10 nmol/L), with no activity against other CDK/cyclin complexes or cell-cycle-related kinases within the nanomolar ranges, except for inhibition of CDK9 at IC50 at least five times higher. The compound was shown to act as a competitive inhibitor of the ATP-binding domain of the CDK4 and CDK6 and to be 14 times more potent against CDK4 than against CDK6. In comparison to palbociclib and ribociclib, abemaciclib shows higher selectivity for the complex CDK4/cyclin D1, with IC50 values five times lower than those of the two other compounds[1].

Synthesis

A concise total synthesis of CDK 4/6 inhibitor abemaciclib is described below. The synthesis uses a Suzuki coupling and a Hartwig–Buchwald amination to join three of the four subunits. The final step is a reductive amination utilizing Leuckart–Wallach conditions. Key to the Leuckart–Wallach reaction was the addition of trimethyl orthoformate to remove water formed during the reaction, allowing the reaction to complete[4].

Enzyme inhibitor

This oral cell cycle inhibitor (FWfree-base = 506.61 g/mol; FWmesylate-salt = 602.70 g/mol; CAS 1231930-82-7 (mesylate salt) ), also known as LY2835219 and N-[5-[ (4-ethyl-1-piperazinyl) methyl]-2-pyridinyl]-5- fluoro-4-[4-fluoro-2-methyl-1- (1-methylethyl) -1H-benzimidazol-6-yl]-2- pyrimidinamine, targets the cyclin-dependent kinase CDK4, or cyclin D1 (IC50 = 2 nM) and CDK6, or cyclin D3 (IC50 = 6 nM), inhibiting retinoblastoma (Rb) protein phosphorylation in early G1, thereby arresting the cell cycle in the G1, suppressing DNA synthesis, and inhibiting cancer cell growth. LY2835219 inhibits activation of AKT and ERK, but not mTOR.

References

[1] Silvia Paola Corona, Daniele Generali. “Abemaciclib: a CDK4/6 inhibitor for the treatment of HR+/HER2- advanced breast cancer.” Drug Design, Development and Therapy (2018): 321–330.
[2] “OS Trending Positive for Abemaciclib.” Cancer discovery 13 1 (2023): OF3.
[3] Erin R Scheidemann. “Resistance to abemaciclib is associated with increased metastatic potential and lysosomal protein deregulation in breast cancer cells.” Molecular Carcinogenesis (2024): 209–223.
[4] Michael O. Frederick, Douglas P. Kjell. “A synthesis of abemaciclib utilizing a Leuckart–Wallach reaction.” Tetrahedron Letters 56 7 (2015): Pages 949-951.

Abemaciclib Preparation Products And Raw materials

Raw materials

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View Lastest Price from Abemaciclib manufacturers

Arizest(Shanghai)Pharmatech Co., Ltd

Product: Abemaciclib 1231929-97-7
Price: US $0.00-0.00/g
Min. Order: 50g
Purity: 99%HPLC
Supply Ability: 5Kg
Release date: 2024-05-08

shandong perfect biotechnology co.ltd

Product: Abemaciclib 1231929-97-7
Price: US $0.00/g
Min. Order: 1g
Purity: 98% HPLC
Supply Ability: 1kg
Release date: 2023-08-02

Hebei Yanxi Chemical Co., Ltd.

Product: Abemaciclib 1231929-97-7
Price: US $0.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 20tons
Release date: 2023-10-11

1231929-97-7, AbemaciclibRelated Search:

LY2090314 LY 2874455 LY-2608204 LY2811376 LY 294002 HYDROCHLORIDE LY 2157299 LY-3177833 LY2603618 LY2334737 ZOSUQUIDAR TRIHYSROCHLORIDE LY-3009120 LY2886721 LY-2584702 (tosylate salt) LY2409881 trihydrochloride LY-364947 LY411575 LY 310762

Abemaciclib, >=98%

Abemaciclib

abemaciclib(CDK 4/6 inhibitor)

Abemaciclib (LY2835219)

Bemaciclib(LY2835219, abemaciclib)

CDK4/6 dual inhibitor

LY 2835219 (free base)

LY2835219 (free base)

LY-2835219 (free base)

N-[5-[(4-Ethyl-1-piperazinyl)methyl]-2-pyridinyl]-5-fluoro-4-[4-fluoro-2-methyl-1-(1-methylethyl)-1H-benzimidazol-6-yl]-2-pyrimidinamine

Abemaciclib free base

ABEMACICLIB BASE

Bemaciclib(LY2835219free base

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

LY2835219(Abemaciclib)

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

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]-

ethyl-1-(propan-2-yl)-1H-benzimidazol-6-yl]pyrimidin-2-amine

LY2835219free base,Abemaciclib

Abemaciclib Mesylate (Verzenio)

CS-814

LY2835219;LY-2835219;LY 2835219;ABEMACICLIB;CDK4/6 DUAL INHIBITOR;LY-2835219 FREE BASE

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

Abemaciclib D10

Abemaciclib D7

inhibit,LY-2835219,LY 2835219,Abemaciclib,Inhibitor,Cyclin dependent kinase,CDK

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

Abemaciclib Powder

abecilee

1231929-97-7

C27H32F2N8

Inhibitors

Pharmaceutical

API

1231929-97-7