dasatinib   Click here for help

GtoPdb Ligand ID: 5678

Synonyms: BMS 345825 | BMS 354825 | BMS 35482513 | Sprycel®
Approved drug PDB Ligand Immunopharmacology Ligand
dasatinib is an approved drug (FDA & EMA (2006))
Compound class: Synthetic organic
Comment: Dasatinib is a Type-1 kinase inhibitor and was first approved by the FDA in 2006.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: dasatinib

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 134.75
Molecular weight 487.16
XLogP 1.99
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES OCCN1CCN(CC1)c1cc(nc(n1)C)Nc1ncc(s1)C(=O)Nc1c(C)cccc1Cl
Isomeric SMILES OCCN1CCN(CC1)c1cc(nc(n1)C)Nc1ncc(s1)C(=O)Nc1c(C)cccc1Cl
InChI InChI=1S/C22H26ClN7O2S/c1-14-4-3-5-16(23)20(14)28-21(32)17-13-24-22(33-17)27-18-12-19(26-15(2)25-18)30-8-6-29(7-9-30)10-11-31/h3-5,12-13,31H,6-11H2,1-2H3,(H,28,32)(H,24,25,26,27)
Immunopharmacology Comments
Dasatinib is reported as a pan-salt inducible kinase (SIK) inhibitor [7]. Dasatinib-induced inhibition of SIK2 has anti-inflammatory action, mediated via induction of a macrophage phentoype switch to a 'regulatory'-like phenotype [7]. These 'regulatory'-like macrophages produce the anti-inflammatory cytokine IL-10 and promote the resolution of inflammation. Inhibition of SIK2 to promote macrophage switch to a 'regulatory'-like phenotype is considered a potential therapeutic strategy for the treatment of chronic inflammatory diseases.