ICOTINIB

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Search structure


Synonyms	BPI-2009H Bpi-2009 Icotinib
Status
Molecule Category	Free-form
ATC	L01EB08
UNII	9G6U5L461Q
EPA CompTox	DTXSID20209952


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	QQLKULDARVNMAL-UHFFFAOYSA-N
Smiles	C#Cc1cccc(Nc2ncnc3cc4c(cc23)OCCOCCOCCO4)c1
InChI	InChI=1S/C22H21N3O4/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)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C22H21N3O4
Molecular Weight	391.43
AlogP	3.16
Hydrogen Bond Acceptor	7.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	2.0
Polar Surface Area	74.73
Molecular species	NEUTRAL
Aromatic Rings	3.0
Heavy Atoms	29.0

Bioactivity

Mechanism of Action	Action	Reference
Epidermal growth factor receptor erbB1 inhibitor	INHIBITOR	PubMed PubMed PubMed


Protein: Epidermal growth factor receptor erbB1 Description: Epidermal growth factor receptor Organism : Homo sapiens P00533 ENSG00000146648

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase EGFR family	-	2-45	-	-	-

Assay Description	Organism	Bioactivity	Reference
Inhibition of EGFR using GST-Crk as substrate assessed as phosphorylated Crk level after 20 mins by SDS-PAGE analysis	None	2.0 nM
Inhibition of EGFR-mediated intracellular tyrosine phosphorylation in EGF-stimulated human A431 cells after 2.5 hrs by SDS-PAGE analysis	Homo sapiens	45.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry.	Homo sapiens	652.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry.	Homo sapiens	725.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry.	Homo sapiens	227.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	68.14 %
Inhibition of EGFR (unknown origin) assessed as reduction of phosphorylation of Crk incubated for 10 mins in ice with gamma-ATP followed by incubated for 20 mins in 30 degC by radioactive phosphorylation assay	Homo sapiens	5.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-2.085 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.29 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.29 %

Related Entries

Cross References

Resources	Reference
ChEMBL	CHEMBL2087361
DrugBank	DB11737
DrugCentral	5209
FDA SRS	9G6U5L461Q
Guide to Pharmacology	7641
PharmGKB	PA166114460
PubChem	22024915
SureChEMBL	SCHEMBL5843603
ZINC	ZINC000043207566

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).