GEFITINIB

U.S. Department of Health & Human Services Divider Arrow

National Institutes of Health Divider Arrow

NCATS

Details

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

SHOW SMILES / InChI

Structure of GEFITINIB

Structure Search

SMILES

COC1=C(OCCCN2CCOCC2)C=C3C(NC4=CC(Cl)=C(F)C=C4)=NC=NC3=C1

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	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:42:15 UTC 2023` Edited by `admin` on `Fri Dec 15 15:42:15 UTC 2023`
Record UNII	S65743JHBS
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

GEFITINIB

Official Name

English

gefitinib [INN]

Common Name

English

GEFITINIB [USAN]

Common Name

English

NSC-759856

Code

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 [WHO-DD]

Common Name

English

GEFITINIB [JAN]

Common Name

English

GEFITINIB [EP MONOGRAPH]

Common Name

English

GEFITINIB [ORANGE BOOK]

Common Name

English

GEFITINIB [MART.]

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 Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

WHO-ATC

L01XE02

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

NCI_THESAURUS

C129825

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

WHO-VATC

QL01XE02

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

EMA ASSESSMENT REPORTS

IRESSA (AUTHORIZED: CARCINOMA, NON-SMALL-CELL LUNG)

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

NDF-RT

N0000175605

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

NDF-RT

N0000175076

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

NCI_THESAURUS

C1967

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

FDA ORPHAN DRUG

443014

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

LIVERTOX

NBK548839

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

Code System Code Type Description

SMS_ID

100000091738

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

WIKIPEDIA

GEFITINIB

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

ChEMBL

CHEMBL939

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

DAILYMED

S65743JHBS

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

EVMPD

SUB20637

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

DRUG BANK

DB00317

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

EPA CompTox

DTXSID8041034

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

FDA UNII

S65743JHBS

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

NCI_THESAURUS

C1855

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

MERCK INDEX

m5682

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

Merck Index

MESH

C419708

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

INN

8204

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

RXCUI

328134

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

RxNorm

IUPHAR

4941

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

CHEBI

49668

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

USAN

NN-73

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

CAS

184475-35-2

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

NSC

759856

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

PUBCHEM

123631

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

DRUG CENTRAL

1282

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

LACTMED

Gefitinib

Created by admin on Fri Dec 15 15:42:15 UTC 2023 , Edited by admin on Fri Dec 15 15:42:15 UTC 2023

PRIMARY

Related Record Type Details


					UN0FN8L6YG

OFF TARGET->NON-INHIBITOR

Comments:

Overall survival (OS) was significantly shorter among patients with uncommon EGFR mutations (G719X or L861Q) com-pared with OS of those with common EGFR mutations (12 versus 28.4 months; p = 0.002). In the gefitinib group (n = 114), patients with uncommon EGFR mutations had a significantly shorter OS (11.9 versus 29.3 months; p < 0.001). By contrast, OS was similar between patients with uncommon mutations and those with common mutations in the carboplatin-paclitaxel group (n = 111; 22.8 versus 28 months; p = 0.358)

Amount:


					AIN96D6SGL

OATP1B1

TRANSPORTER -> SUBSTRATE


					66DDF797LP

OATP-8

TRANSPORTER -> SUBSTRATE


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Comments:

In vitro binding of gefitinib to human plasma proteins (serum albumin and α1-acid glycoprotein) is 90% and is independent of drug concentrations.

Interaction Type:

BINDING

Amount:


					482M00274D

OCT-2

TRANSPORTER -> INHIBITOR


					RO03J093CP

EPIDERMAL GROWTH FACTOR RECEPTOR

TARGET -> INHIBITOR

Amount:


					4007E25Z4Z

OCT-3

TRANSPORTER -> INHIBITOR


					76UB6O122H

ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2

TRANSPORTER -> INDUCER


					22ES734693

MULTIDRUG RESISTANCE PROTEIN 1

TRANSPORTER -> INHIBITOR

Amount:


					9DX651UO0D

CYTOCHROME P450 1A1

METABOLIC ENZYME -> INHIBITOR

Qualification:

Ki

Amount:


					482M00274D

OCT-2

TRANSPORTER -> SUBSTRATE

Related Record Type Details


					MNV6L4WJV9

GEFITINIB-2,5-CYCLOHEXADIEN-1-ONE, 2-CHLORO-4-IMINO-

METABOLITE -> PARENT

Amount:


					26K9JW7RGU

3-(4-(3-CHLORO-4-FLUORO-ANILINO)-7-METHOXY-QUINAZOLIN-6-YL)OXYPROPANOIC ACID

METABOLITE -> PARENT

Amount:

Related Record Type Details


					R9YH59H93M

7-methoxy-6-[3-(4-morpholinyl)propoxy]-4(3H)-quinazolinone

IMPURITY -> PARENT

Amount:

Related Record Type Details


					S65743JHBS

GEFITINIB

ACTIVE MOIETY

Amount:

Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Tmax	PHARMACOKINETIC				ORAL ADMINISTRATION

Biological Half-life	PHARMACOKINETIC

Volume of Distribution	PHARMACOKINETIC				AT STEADY-STATE INTRAVENOUS ADMINISTRATION

ORAL BIOAVAILABILITY	PHARMACOKINETIC