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Category Antineoplastic
Catalog number BBF-05853
CAS 571190-30-2
Molecular Weight 447.53
Molecular Formula C24H29N7O2
Purity >95%

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BBF-05853 5 g $298 In stock

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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.


Related CAS 827022-32-2 (HCl) 827022-33-3 (Isethionate)
Synonyms PD 0332991; PD0332991; PD-0332991; Ibrance; 6-Acetyl-8-cyclopentyl-5-methyl-2-[[5-(piperazin-1-yl)pyridin-2-yl]amino]-8H-pyrido[2,3-d]pyrimidin-7-one; 6-Acetyl-8-cyclopentyl-5-methyl-2-((5-(piperazin-1-yl)pyridin-2-yl)amino)pyrido[2,3-d]pyrimidin-7(8H)-one
Storage Store at 2-8°C
IUPAC Name 6-acetyl-8-cyclopentyl-5-methyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one
Canonical SMILES CC1=C(C(=O)N(C2=NC(=NC=C12)NC3=NC=C(C=C3)N4CCNCC4)C5CCCC5)C(=O)C
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)


Appearance Pale Yellow to Green Solid
Antibiotic Activity Spectrum Neoplastics (Tumor)
Boiling Point 711.5±70.0°C at 760 mmHg
Melting Point >244°C (dec.)
Density 1.3±0.1 g/cm3
Solubility Soluble in Chloroform (Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated)

Reference Reading

1.Palbociclib:CDK4/6 inhibition in the treatment of ER-positive breast cancer.
Owsley J1, Jimeno A2, Diamond JR1. Drugs Today (Barc). 2016 Feb;52(2):119-29. doi: 10.1358/dot.2016.52.2.2440528.
Maintaining cell-cycle control has become a mainstay in treatment for many cancers. Cell-cycle manipulation can be especially valuable in breast cancer tumor cells that will often express hormone receptors that are amenable to anti-hormone receptor-targeted therapies. Despite these treatments, patients often progress, leading to other targeted agents being investigated to help promote progression-free survival. Cyclin-dependent kinases (CDKs) have been identified as contributors in the process of cell division. Combining inhibitors of CDKs with traditional endocrine treatments has shown significant progression-free survival in patients with metastatic breast cancer. One such CDK inhibitor, palbociclib, has shown great promise in the treatment of hormone receptor-positive breast cancer. In this article we review the traditional hormonal treatments of breast cancer, how CDK inhibition is beneficial in the treatment of this disease, and the preclinical and clinical data supporting the use of this medication.
2.Isolation and Structural Elucidation of Palbociclib's Eight Process-Related Impurities: Two Identified as New Compounds.
J AOAC Int. 2016 Apr 19. [Epub ahead of print]
Palbociclib is the first U.S. Food and Drug Administration-approved cyclin-dependent kinase inhibitor indicated in combination with letrozole for the treatment of breast cancer. Development of a selective method for the determination of any impurities contained in this drug is significantly important to ensure the quality and safety of palbociclib. In this study, a reliable reversed-phase HPLC method for the separation and determination of eight potential impurities was developed and validated. The structures of two new compounds and six other process-related impurities were characterized and confirmed by MS, NMR, and IR. Based on spectral analysis and available knowledge of the synthetic route of palbociclib, these two new compounds were designated as 6-acetyl-8-cyclopentyl-5-methyl-2-{[3-(piperazin-1-yl)pyridin-2yl]amino}pyrido [2,3-d]pyrimidin-7(8H)-one and 6-acetyl-8-cyclopentyl-5-methyl-2-{[5-(4-t-butyloxycarbonyl-)-(piperazin-1-yl)pyridin-2yl]amino}pyrido [2,3-d]pyrimidin-7(8H)-one.
3.Palbociclib treatment of FLT3-ITD+ AML cells uncovers a kinase-dependent transcriptional regulation of FLT3 and PIM1 by CDK6.
Uras IZ1, Walter GJ2, Scheicher R1, Bellutti F1, Prchal-Murphy M1, Tigan AS1, Valent P3, Heidel FH4, Kubicek S5, Scholl C6, Fröhling S7, Sexl V8. Blood. 2016 Apr 20. pii: blood-2015-11-683581. [Epub ahead of print]
Up to 30% of patients with acute myeloid leukemia (AML) have constitutively activating internal tandem duplications (ITDs) of the FLT3 receptor tyrosine kinase. Such mutations are associated with a poor prognosis and a high propensity to relapse after remission. FLT3 inhibitors are being developed as targeted therapy forFLT3-ITD+AML; however, their use is complicated by rapid development of resistance, illustrating the need for additional therapeutic targets. We show that the FDA-approved CDK4/6 kinase inhibitor palbociclib induces apoptosis of FLT3-ITD leukemic cells. The effect is specific forFLT3-mutant cells and is ascribed to the transcriptional activity of CDK6: CDK6 but not its functional homolog CDK4 is found at the promoters of theFLT3andPIM1genes, another important leukemogenic driver. There CDK6 regulates transcription in a kinase-dependent manner. Of potential clinical relevance combined treatment with palbociclib and FLT3 inhibitors results in synergistic cytotoxicity.
4.Progression-Free Survival Among Patients With Well-Differentiated or Dedifferentiated Liposarcoma Treated With CDK4 Inhibitor Palbociclib: A Phase 2 Clinical Trial.
Dickson MA1, Schwartz GK2, Keohan ML1, D'Angelo SP1, Gounder MM1, Chi P1, Antonescu CR3, Landa J4, Qin LX5, Crago AM6, Singer S6, Koff A7, Tap WD1. JAMA Oncol. 2016 Apr 28. doi: 10.1001/jamaoncol.2016.0264. [Epub ahead of print]
Importance: More than 90% of well-differentiated or dedifferentiated liposarcomas (WD/DDLS) have CDK4 amplification. The selective CDK4 and CDK6 inhibitor palbociclib inhibits growth and induces senescence in liposarcoma cell lines and xenografts. Our prior phase 2 study demonstrated that treatment with palbociclib (200 mg daily for 14 days every 21 days) resulted in clinical benefit in WD/DDLS but moderate hematologic toxic effects. It is important to understand whether palbociclib at a new dose and schedule-125 mg daily for 21 days every 28 days-results in clinical benefit and manageable toxic effects.

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