CHEBI:47458 - saracatinib

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ChEBI Name saracatinib
ChEBI ID CHEBI:47458
Definition A member of the class of quinazolines that is quinazoline substituted by (5-chloro-2H-1,3-benzodioxol-4-yl)amino, (oxan-4-yl)oxy and 2-(4-methylpiperazin-1-yl)ethoxy groups at positions 4, 5 and 7, respectively. It is a dual inhibitor of the tyrosine kinases c-Src and Abl (IC50 = 2.7 and 30 nM, respectively). Saracatinib was originally developed by AstraZeneca for the treatment of cancer but in 2019 it was granted orphan drug designation by the US Food and Drug Administration for the treatment of idiopathic pulmonary fibrosis (IPF), a type of lung disease that results in scarring (fibrosis) of the lungs.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C27H32ClN5O5
Net Charge 0
Average Mass 542.030
Monoisotopic Mass 541.20920
InChI InChI=1S/C27H32ClN5O5/c1-32-6-8-33(9-7-32)10-13-35-19-14-21-24(23(15-19)38-18-4-11-34-12-5-18)27(30-16-29-21)31-25-20(28)2-3-22-26(25)37-17-36-22/h2-3,14-16,18H,4-13,17H2,1H3,(H,29,30,31)
InChIKey OUKYUETWWIPKQR-UHFFFAOYSA-N
SMILES CN1CCN(CCOC2=CC(OC3CCOCC3)=C3C(NC4=C(Cl)C=CC5=C4OCO5)=NC=NC3=C2)CC1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
An EC 2.7.10.* (protein-tyrosine kinase) inhibitor that specifically blocks the action of non-specific protein-tyrosine kinase (EC 2.7.10.2).
autophagy inducer
Any compound that induces the process of autophagy (the self-digestion of one or more components of a cell through the action of enzymes originating within the same cell).
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
anticoronaviral agent
Any antiviral agent which inhibits the activity of coronaviruses.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
radiosensitizing agent
A drug that makes increases the sensitivity of tumour cells to radiation therapy.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing saracatinib (CHEBI:47458) has role anticoronaviral agent (CHEBI:149553)
saracatinib (CHEBI:47458) has role antineoplastic agent (CHEBI:35610)
saracatinib (CHEBI:47458) has role apoptosis inducer (CHEBI:68495)
saracatinib (CHEBI:47458) has role autophagy inducer (CHEBI:138880)
saracatinib (CHEBI:47458) has role EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor (CHEBI:76617)
saracatinib (CHEBI:47458) has role radiosensitizing agent (CHEBI:132992)
saracatinib (CHEBI:47458) is a N-methylpiperazine (CHEBI:46920)
saracatinib (CHEBI:47458) is a aromatic ether (CHEBI:35618)
saracatinib (CHEBI:47458) is a benzodioxoles (CHEBI:38298)
saracatinib (CHEBI:47458) is a diether (CHEBI:46786)
saracatinib (CHEBI:47458) is a organochlorine compound (CHEBI:36683)
saracatinib (CHEBI:47458) is a oxanes (CHEBI:46942)
saracatinib (CHEBI:47458) is a quinazolines (CHEBI:38530)
saracatinib (CHEBI:47458) is a secondary amino compound (CHEBI:50995)
IUPAC Name
N-(5-chloro-1,3-benzodioxol-4-yl)-7-[2-(4-methylpiperazin-1-yl)ethoxy]-5-(tetrahydro-2H-pyran-4-yloxy)quinazolin-4-amine
INNs Sources
saracatinib WHO MedNet
saracatinib WHO MedNet
saracatinib WHO MedNet
saracatinibum WHO MedNet
Synonyms Sources
AZ-10353926 LINCS
AZD 0530 ChemIDplus
AZD-0530 LINCS
AZD0530 ChemIDplus
N-(5-chloro-1,3-benzodioxol-4-yl)-7-[2-(4-methyl-1-piperazinyl)ethoxy]-5-[(tetrahydro-2H-pyran-4-yl)oxy]-4-quinazolinamine ChEBI
N-(5-chloro-2H-1,3-benzodioxol-4-yl)-7-[2-(4-methylpiperazin-1-yl)ethoxy]-5-[(oxan-4-yl)oxy]quinazolin-4-amine IUPAC
Manual Xrefs Databases
8477917 ChemSpider
D09664 KEGG DRUG
DB11805 DrugBank
H8H PDBeChem
LSM-1032 LINCS
Saracatinib Wikipedia
View more database links
Registry Number Type Source
379231-04-6 CAS Registry Number ChemIDplus
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Last Modified
16 July 2021