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Details

Stereochemistry ACHIRAL
Molecular Formula C22H24ClFN4O3
Molecular Weight 446.902
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GEFITINIB

SMILES

COC1=CC2=NC=NC(NC3=CC(Cl)=C(F)C=C3)=C2C=C1OCCCN4CCOCC4

InChI

InChIKey=XGALLCVXEZPNRQ-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C22H24ClFN4O3
Molecular Weight 446.902
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Gefitinib is an anilinoquinazoline with antineoplastic activity. Gefitinib inhibits the epidermal growth factor receptor (EGFR) tyrosine kinase by binding to the adenosine triphosphate (ATP)-binding site of the enzyme. Thus the function of the EGFR tyrosine kinase in activating the Ras signal transduction cascade is inhibited; and malignant cells are inhibited. Gefitinib is the first selective inhibitor of the EGFR tyrosine kinase which is also referred to as Her1 or ErbB-1. EGFR is overexpressed in the cells of certain types of human carcinomas - for example in lung and breast cancers. Overexpression leads to inappropriate activation of the apoptotic Ras signal transduction cascade, eventually leading to uncontrolled cell proliferation. Gefitinib is used for the continued treatment of patients with locally advanced or metastatic non-small cell lung cancer after failure of either platinum-based or docetaxel chemotherapies.

CNS Activity

Originator

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Iressa
PubMed

PubMed

TitleDatePubMed
Prospects for combining hormonal and nonhormonal growth factor inhibition.
2001 Dec
OSI Pharmaceuticals, Genentech and Roche announce data from clinical studies of Tarceva.
2001 Jun
[3rd National Congress of Medical Oncology. Issues in Gynecologic Oncology. Naples, November 7, 2000].
2001 Nov-Dec
Gefitinib.
2002
ZD1839 (Iressa): what's in it for the patient?
2002
ZD1839 (Iressa) in non-small cell lung cancer.
2002
Why the epidermal growth factor receptor? The rationale for cancer therapy.
2002
Cytotoxic agents in the era of molecular targets and genomics.
2002
93rd Annual Meeting of the American Association for Cancer Research, San Francisco, CA, USA, 6-10 April 2002.
2002
Finding the needle in the haystack: why high-throughput screening is good for your health.
2002
ZD1839 (IRESSA): a selective EGFR-TK inhibitor.
2002 Apr
ZD1839 ('Iressa'), a specific oral epidermal growth factor receptor-tyrosine kinase inhibitor, potentiates radiotherapy in a human colorectal cancer xenograft model.
2002 Apr 8
A serum factor after intestinal resection stimulates epidermal growth factor receptor signaling and proliferation in intestinal epithelial cells.
2002 Aug
[New therapeutic targets and strategies in lung cancer].
2002 Aug
Epidermal growth factor receptor tyrosine kinase inhibitors.
2002 Aug
Modulation of radiation response and tumor-induced angiogenesis after epidermal growth factor receptor inhibition by ZD1839 (Iressa).
2002 Aug 1
Activation of BAD by therapeutic inhibition of epidermal growth factor receptor and transactivation by insulin-like growth factor receptor.
2002 Aug 2
Inhibition of apoptosis by amphiregulin via an insulin-like growth factor-1 receptor-dependent pathway in non-small cell lung cancer cell lines.
2002 Dec 20
[Molecular target-based cancer therapy: epidermal growth factor receptor inhibitors].
2002 Feb
[Non surgical new treatment modalities for lung cancer].
2002 Feb
ZD1839, a selective epidermal growth factor receptor tyrosine kinase inhibitor, alone and in combination with radiation and chemotherapy as a new therapeutic strategy in non-small cell lung cancer.
2002 Feb
Targeting the EGF receptor in ovarian cancer with the tyrosine kinase inhibitor ZD 1839 ("Iressa").
2002 Feb 1
ZD1839 (Iressa): preclinical studies and pharmacology.
2002 Jan-Feb
Gateways to Clinical Trials. June 2002.
2002 Jun
HER (erbB) tyrosine kinase inhibitors in the treatment of breast cancer.
2002 Jun
Molecular mechanisms in signal transduction: new targets for the therapy of gynecologic malignancies.
2002 Jun
Modulation of epidermal growth factor receptor in endocrine-resistant, estrogen-receptor-positive breast cancer.
2002 Jun
Selective inhibition of the epidermal growth factor receptor impairs intestinal adaptation after small bowel resection.
2002 Jun 1
A sensitive assay for ZD1839 (Iressa) in human plasma by liquid-liquid extraction and high performance liquid chromatography with mass spectrometric detection: validation and use in Phase I clinical trials.
2002 Jun 20
Cancer medicine hits a target.
2002 Jun 3
Local recurrence in head and neck cancer: relationship to radiation resistance and signal transduction.
2002 Mar
[Progress in diagnosis and treatment of lung cancer].
2002 Mar 20
ZD1839 (IRESSA), an EGFR-selective tyrosine kinase inhibitor, enhances taxane activity in bcl-2 overexpressing, multidrug-resistant MCF-7 ADR human breast cancer cells.
2002 Mar 20
Sequence-dependent effects of ZD1839 ('Iressa') in combination with cytotoxic treatment in human head and neck cancer.
2002 Mar 4
[Future trends in anticancer chemotherapy].
2002 May
[Latest therapeutic strategy for stage IV non-small cell lung cancer].
2002 May
[ZD1839].
2002 May
Bradykinin antagonist dimer, CU201, inhibits the growth of human lung cancer cell lines in vitro and in vivo and produces synergistic growth inhibition in combination with other antitumor agents.
2002 May
Targeting the epidermal growth factor receptor with tyrosine kinase inhibitors: small molecules, big hopes.
2002 May 1
ZD1839 (Iressa) induces antiangiogenic effects through inhibition of epidermal growth factor receptor tyrosine kinase.
2002 May 1
The epidermal growth factor receptor: a new target for anticancer therapy.
2002 May-Jun
Despite concerns, FDA panel backs EGFR inhibitor.
2002 Nov 6
Molecular characterization as a target for cancer therapy in relation to orphan status disorders (Review).
2002 Nov-Dec
Surprise phase III failure for ZD1839.
2002 Oct
The role of EGFR-directed therapy in the treatment of breast cancer.
2002 Oct
Cancer drugs. Smart weapons prove tough to design.
2002 Oct 18
Syntheses and EGFR and HER-2 kinase inhibitory activities of 4-anilinoquinoline-3-carbonitriles: analogues of three important 4-anilinoquinazolines currently undergoing clinical evaluation as therapeutic antitumor agents.
2002 Oct 21
Inhibition of epidermal growth factor receptor signaling in malignant pleural mesothelioma.
2002 Sep 15
Selective oral epidermal growth factor receptor tyrosine kinase inhibitor ZD1839 is generally well-tolerated and has activity in non-small-cell lung cancer and other solid tumors: results of a phase I trial.
2002 Sep 15
Gefitinib (Iressa) for advanced non-small cell lung cancer.
2002 Sep 2
Patents

Sample Use Guides

In Vivo Use Guide
250 mg orally once a day
Route of Administration: Oral
In Vitro Use Guide
Gefitinib could inhibit highly expressed EGFR cell growth in a dose-dependent manner in the range of dose from 0.10 to 102.4 uM
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:50:03 UTC 2019
Edited
by admin
on Mon Oct 21 20:50:03 UTC 2019
Record UNII
S65743JHBS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GEFITINIB
EMA EPAR   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
GEFITINIB [INN]
Common Name English
GEFITINIB [USAN]
Common Name English
4-QUINAZOLINAMINE, N-(3-CHLORO-4-FLUOROPHENYL)-7-METHOXY-6-(3-4-MORPHOLIN)PROPOXY)-
Common Name English
GEFITINIB [EMA EPAR]
Common Name English
ZD-1839
Code English
GEFITINIB [VANDF]
Common Name English
IRESSA
Brand Name English
GEFITINIB [JAN]
Common Name English
GEFITINIB [ORANGE BOOK]
Common Name English
GEFITINIB [MART.]
Common Name English
GEFITINIB [WHO-DD]
Common Name English
GEFITINIB [MI]
Common Name English
ZD1839
Code English
Classification Tree Code System Code
EU-Orphan Drug EU/3/18/2075
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
WHO-ATC L01XE02
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
NCI_THESAURUS C129825
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
WHO-VATC QL01XE02
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
EMA ASSESSMENT REPORTS IRESSA (AUTHORIZED: CARCINOMA, NON-SMALL-CELL LUNG)
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
NDF-RT N0000175605
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
NDF-RT N0000175076
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
NCI_THESAURUS C1967
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
FDA ORPHAN DRUG 443014
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
LIVERTOX 450
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
Code System Code Type Description
WIKIPEDIA
GEFITINIB
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
PRIMARY
ChEMBL
CHEMBL939
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
PRIMARY
EVMPD
SUB20637
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
PRIMARY
DRUG BANK
DB00317
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
PRIMARY
EPA CompTox
184475-35-2
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
PRIMARY
NCI_THESAURUS
C1855
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
PRIMARY
MERCK INDEX
M5682
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
PRIMARY Merck Index
MESH
C419708
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
PRIMARY
INN
8204
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
PRIMARY
RXCUI
328134
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
PRIMARY RxNorm
IUPHAR
4941
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
PRIMARY
LactMed
184475-35-2
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
PRIMARY
CAS
184475-35-2
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
PRIMARY
PUBCHEM
123631
Created by admin on Mon Oct 21 20:50:03 UTC 2019 , Edited by admin on Mon Oct 21 20:50:03 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
TARGET -> INHIBITOR
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INDUCER
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY