palbociclib   Click here for help

GtoPdb Ligand ID: 7380

Synonyms: Ibrance® | PD-0332991 | PD0332991
Approved drug PDB Ligand
palbociclib is an approved drug (FDA (2015), EMA (2016))
Compound class: Synthetic organic
Comment: Palbociclib is a selective inhibitor of the cyclin-dependent kinases CDK4 and CDK6 [6-7,14]. This kinase inhibitor has anti-tumour activity in several tumour models [6-7,9,15-16].
The pharmaceutical formulation contains palbociclib isethionate (PubChem CID 11478676).
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: palbociclib

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 105.04
Molecular weight 447.24
XLogP 3.29
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES CC(=O)c1c(C)c2cnc(nc2n(c1=O)C1CCCC1)Nc1ccc(cn1)N1CCNCC1
Isomeric SMILES CC(=O)c1c(C)c2cnc(nc2n(c1=O)C1CCCC1)Nc1ccc(cn1)N1CCNCC1
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)
Bioactivity Comments
Palbociclib acts via inhibition of CDK4/6 to dose-dependently reduce phosphorylation of the retinoblastoma protein (Rb) with an IC50 of 30nM [15] in both MV4-11 and MOLM13 acute myelocytic leukemia (AML) cell lines.
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
cyclin dependent kinase 4 Primary target of this compound Hs Inhibitor Inhibition 7.4 – 8.5 pIC50 - 7,12-13
pIC50 8.5 (IC50 3.2x10-9 M) [12]
pIC50 8.0 (IC50 1.1x10-8 M) [7]
pIC50 7.4 (IC50 4.4x10-8 M) [13]
cyclin dependent kinase 6 Primary target of this compound Hs Inhibitor Inhibition 7.4 – 8.0 pIC50 - 7,12-13
pIC50 8.0 (IC50 1.1x10-8 M) [12]
pIC50 7.8 (IC50 1.6x10-8 M) [7]
pIC50 7.4 (IC50 3.6x10-8 M) [13]
Ligand mentioned in the following text fields