Stereochemistry | ACHIRAL |
Molecular Formula | C22H21N3O4.ClH |
Molecular Weight | 427.881 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.C#CC1=CC(NC2=NC=NC3=C2C=C4OCCOCCOCCOC4=C3)=CC=C1
InChI
InChIKey=PNNGXMJMUUJHAV-UHFFFAOYSA-N
InChI=1S/C22H21N3O4.ClH/c1-2-16-4-3-5-17(12-16)25-22-18-13-20-21(14-19(18)23-15-24-22)29-11-9-27-7-6-26-8-10-28-20;/h1,3-5,12-15H,6-11H2,(H,23,24,25);1H
Icotinib is an orally available quinazoline-based inhibitor of epidermal growth factor receptor. It selectively inhibits the wild-type and several mutated forms of EGFR tyrosine kinase. The major organ of icotinib metabolism is the liver, with the primarily enzymes being CYP2C19 and CYP3A4 from the cytochrome P450 monooxygenase system. Icotinib Hydrochloride was approved for the treatment of patients with advanced stage Nonsmall cell lung cancer by the State Food and Drug Administration (SFDA) of China. The major drug related adverse reactions of the traditional cytotoxic agents include rash, diarrhea, severe bone marrow suppression, neuropathy, hair loss, and gastrointestinal reactions. Icotinib is under investigation as an active agent against other EGFR mutation-positive cancers, like lung adenocarcinoma, oesophageal cancer, nasopharyngeal cancer and others.
CNS Activity
Originator
Approval Year
Doses
AEs
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
PubMed
Patents
Sample Use Guides
Icotinib induces G1 phase cell cycle arrest and apoptosis in HCC827 cells. There was an increase in the number of cells in G1 phase after exposure to 0.01 and 0.1 uM icotinib for 24 h. The percentage of cells in G1 phase increased from 45.41 to 68.41 and 78.30, respectively. Furthermore, the percentages of apoptotic cells were elevated from 4.26% to 6.31% and 18.85%, after treatment with 0.01 and 0.1 uM icotinib.