gefitinib (CHEBI:49668)

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CHEBI:49668 - gefitinib

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ChEBI Name	gefitinib

ChEBI ID	CHEBI:49668

Definition	A member of the class of quinazolines that is quinazoline which is substituted by a (3-chloro-4-fluorophenyl)nitrilo group, 3-(morpholin-4-yl)propoxy group and a methoxy group at positions 4,6 and 7, respectively. An EGFR kinase inhibitor used for the treatment of non-small cell lung cancer.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:38917, CHEBI:49667

Supplier Information	ChemicalBook:CB8120056, eMolecules:876432, Selleckchem:Gefitinib, ZINC000019632614

Download	Molfile XML SDF

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M END): 29 ms

reading 55 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

55 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Gefitinib, sold under the brand name Iressa, is a medication used for certain breast, lung and other cancers. Gefitinib is an EGFR inhibitor, like erlotinib, which interrupts signaling through the epidermal growth factor receptor (EGFR) in target cells. Therefore, it is only effective in cancers with mutated and overactive EGFR, but resistances to gefitinib can arise through other mutations. It is marketed by AstraZeneca and Teva. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.
Read full article at Wikipedia

Formula

C22H24ClFN4O3

Net Charge

Average Mass

446.910

Monoisotopic Mass

446.15210

InChI

InChI=1S/C22H24ClFN4O3/c1-29-20-13-19-16(12-21(20)31-8-2-5-28-6-9-30-10-7-28)22(26-14-25-19)27-15-3-4-18(24)17(23)11-15/h3-4,11-14H,2,5-10H2,1H3,(H,25,26,27)

InChIKey

XGALLCVXEZPNRQ-UHFFFAOYSA-N

SMILES

C1=C(C(=CC=2C1=NC=NC2NC3=CC(=C(C=C3)F)Cl)OCCCN4CCOCC4)OC

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):	epidermal growth factor receptor antagonist An antagonist at the epidermal growth factor receptor.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	gefitinib (CHEBI:49668) has role antineoplastic agent (CHEBI:35610) gefitinib (CHEBI:49668) has role epidermal growth factor receptor antagonist (CHEBI:74440) gefitinib (CHEBI:49668) is a aromatic ether (CHEBI:35618) gefitinib (CHEBI:49668) is a monochlorobenzenes (CHEBI:83403) gefitinib (CHEBI:49668) is a monofluorobenzenes (CHEBI:83575) gefitinib (CHEBI:49668) is a morpholines (CHEBI:38785) gefitinib (CHEBI:49668) is a quinazolines (CHEBI:38530) gefitinib (CHEBI:49668) is a secondary amino compound (CHEBI:50995) gefitinib (CHEBI:49668) is a tertiary amino compound (CHEBI:50996)

Incoming	linkable gefitinib analogue (CHEBI:39084) has functional parent gefitinib (CHEBI:49668)

IUPAC Name

N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine

INNs	Sources
géfitinib	WHO MedNet
gefitinib	WHO MedNet
gefitinib	WHO MedNet
gefitinibum	WHO MedNet

Synonyms	Sources
4-(3'-chloro-4'-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazoline	ChemIDplus
N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-(4-morpholinyl)propoxy)-4-quinazolinamine	ChemIDplus
ZD 1839	ChemIDplus
ZD-1839	DrugBank
ZD1839	DrugCentral

Brand Names	Sources
Iressa	ChemIDplus
Irressat	ChemIDplus

Manual Xrefs	Databases
1282	DrugCentral
D01977	KEGG DRUG
DB00317	DrugBank
Gefitinib	Wikipedia
HMDB0014462	HMDB
IRE	PDBeChem
LSM-1098	LINCS
View more database links

Registry Numbers	Types	Sources
184475-35-2	CAS Registry Number	ChemIDplus
8949523	Reaxys Registry Number	Reaxys

Citations

Last Modified

28 May 2019

CHEBI:49668 - gefitinib

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