LQQ

6-ACETYL-8-CYCLOPENTYL-5-METHYL-2-[(5-PIPERAZIN-1-YLPYRIDIN-2-YL)AMINO]PYRIDO[2,3-D]PYRIMIDIN-7(8H)-ONE

Created: 2005-11-28
Last modified:  2021-03-01

Help

Find related ligands:

Chemical Details

Formal Charge0
Atom Count62
Chiral Atom Count0
Bond Count66
Aromatic Bond Count17
2D diagram of LQQ
Toggle HydrogenToggle Labels

Chemical Component Summary

Name6-ACETYL-8-CYCLOPENTYL-5-METHYL-2-[(5-PIPERAZIN-1-YLPYRIDIN-2-YL)AMINO]PYRIDO[2,3-D]PYRIMIDIN-7(8H)-ONE
SynonymsPalbociclib
Systematic Name (OpenEye OEToolkits)8-cyclopentyl-6-ethanoyl-5-methyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[6,5-d]pyrimidin-7-one
FormulaC24 H29 N7 O2
Molecular Weight447.533
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C2N(c1nc(ncc1C(=C2C(=O)C)C)Nc3ncc(cc3)N4CCNCC4)C5CCCC5
SMILESCACTVS3.341CC(=O)C1=C(C)c2cnc(Nc3ccc(cn3)N4CCNCC4)nc2N(C5CCCC5)C1=O
SMILESOpenEye OEToolkits1.5.0CC1=C(C(=O)N(c2c1cnc(n2)Nc3ccc(cn3)N4CCNCC4)C5CCCC5)C(=O)C
Canonical SMILESCACTVS3.341 CC(=O)C1=C(C)c2cnc(Nc3ccc(cn3)N4CCNCC4)nc2N(C5CCCC5)C1=O
Canonical SMILESOpenEye OEToolkits1.5.0 CC1=C(C(=O)N(c2c1cnc(n2)Nc3ccc(cn3)N4CCNCC4)C5CCCC5)C(=O)C
InChIInChI1.03 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)
InChIKeyInChI1.03 AHJRHEGDXFFMBM-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB09073 
NamePalbociclib
Groups
  • approved
  • investigational
DescriptionPalbociclib is a piperazine pyridopyrimidine[A176792] that acts in the cell cycle machinery. It is a second generation cyclin-dependent kinase inhibitor[A176798] selected from a group of pyridopyrimidine compounds due to its favorable physical and pharmaceutical properties.[A176810] Palbociclib was developed by Pfizer Inc after the discovery that identified the cyclin-dependent kinases as key regulators of cell growth.[L5867] It was originally FDA approved on March 2015 for the treatment of HR-positive, HER2-negative advanced or metastatic breast cancer and its indications were updated in April 2019 to include male patients based on findings from postmarketing reports and electronic health records demonstrating safety and clinical efficacy.[L4894]
Synonyms
  • 6-acetyl-8-cyclopentyl-5-methyl-2-{[5-(piperazin-1-yl)pyridin-2-yl]amino}pyrido[2,3-d]pyrimidin-7(8H)-one
  • Palbociclib
  • Palbociclib isethionate
Brand NamesIbrance
IndicationPalbociclib is indicated in combination with [letrozole] as initial endocrine-based therapy for the treatment of human epidermal growth factor receptor type 2 (HER2)-negative and hormone receptor(HR)-positive tumors in adult patients with advanced/metastatic breast cancer. It is as well approved in combination with [fulvestrant] in patients with disease progression with prior endocrine therapy.[A176783] In the official labeling, the use of palbociclib should be accompanied with either an aromatase inhibition, no restricted to letrozole, as initial endocrine-based therapy in postmenopausal women or in man.[L48076] The breast cancer starts as a group of cancer cells that grow into and destroy the nearby breast tissue. This growth can spread into other parts of the body which is called metastasis. According to the location of the cancer cells, it can be categorized in ductal carcinoma and lobular carcinoma. However, other types of breast cancer include inflammatory breast cancer, Paget disease of the breast, triple negative breast cancer non-Hodgkin lymphoma and soft tissue sarcoma.[L5870] In males, breast cancer is usually treated as the cases of postmenopausal women and almost all the cases are ductal carcinoma.[L5873]
Categories
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • BCRP/ABCG2 Inhibitors
  • BCRP/ABCG2 Substrates
  • Cyclin-dependent kinase (CDK) inhibitors
ATC-CodeL01EF01
CAS number571190-30-2

Drug Targets

NameTarget SequencePharmacological ActionActions
Cyclin-dependent kinase 4MATSRYEPVAEIGVGAYGTVYKARDPHSGHFVALKSVRVPNGGGGGGGLP...unknowninhibitor
Cyclin-dependent kinase 6MEKDGLCRADQQYECVAEIGEGAYGKVFKARDLKNGGRFVALKRVRVQTG...unknowninhibitor
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inhibitor
Bile salt sulfotransferaseMSDDFLWFEGIAFPTMGFRSETLRKVRDEFVIRDEDVIILTYPKSGTNWL...unknownsubstrate
Serum albuminMKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...unknownbinder
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL189963
PubChem 5330286
ChEMBL CHEMBL189963
ChEBI CHEBI:85993
CCDC/CSD OSUHAO