U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C22H23N3O4
Molecular Weight 393.4357
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ERLOTINIB

SMILES

COCCOC1=CC2=NC=NC(NC3=CC=CC(=C3)C#C)=C2C=C1OCCOC

InChI

InChIKey=AAKJLRGGTJKAMG-UHFFFAOYSA-N
InChI=1S/C22H23N3O4/c1-4-16-6-5-7-17(12-16)25-22-18-13-20(28-10-8-26-2)21(29-11-9-27-3)14-19(18)23-15-24-22/h1,5-7,12-15H,8-11H2,2-3H3,(H,23,24,25)

HIDE SMILES / InChI
Molecular Formula C22H23N3O4
Molecular Weight 393.4357
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Erlotinib hydrochloride (trade name Tarceva, Genentech/OSIP, originally coded as OSI-774) is a drug used to treat non-small cell lung cancer, pancreatic cancer and several other types of cancer. Similar to gefitinib, erlotinib specifically targets the epidermal growth factor receptor (EGFR) tyrosine kinase. It binds in a reversible fashion to the adenosine triphosphate (ATP) binding site of the receptor. Erlotinib has recently been shown to be a potent inhibitor of JAK2V617F activity. JAK2V617F is a mutant of tyrosine kinase JAK2, is found in most patients with polycythemia vera (PV) and a substantial proportion of patients with idiopathic myelofibrosis or essential thrombocythemia. The study suggests that erlotinib may be used for treatment of JAK2V617F-positive PV and other myeloproliferative disorders. The mechanism of clinical antitumor action of erlotinib is not fully characterized. Erlotinib inhibits the intracellular phosphorylation of tyrosine kinase associated with the epidermal growth factor receptor (EGFR). Specificity of inhibition with regard to other tyrosine kinase receptors has not been fully characterized. EGFR is expressed on the cell surface of normal cells and cancer cells.

CNS Activity

Originator

Approval Year

2004
75
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2438
Carcinoma, Non-Small-Cell Lung
 1.2 nM [IC50]
Antagonist
2438
Carcinoma, Non-Small-Cell Lung
 0.05 µM [IC50]
Inhibitor
7197
Carcinoma, Non-Small-Cell Lung
 2.23 µM [IC50]
Inhibitor
7197
Pancreatic Neoplasms
 0.02 µM [IC50]
Inhibitor
7197
 0.08 µM [IC50]
Agonist
2314
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Epidermal growth factor receptor
Epidermal growth factor receptor erbB1
PANC-1
Approved
7777
TARCEVA
Primary
Epidermal growth factor receptor
ATP-binding cassette sub-family G member 2
Epidermal growth factor receptor erbB1
Approved
7777
TARCEVA
PubMed

PubMed

TitleDatePubMed
Small-molecule epidermal growth factor receptor tyrosine kinase inhibitors.
2003
Development of the epidermal growth factor receptor inhibitor Tarceva (OSI-774).
2003
Erlotinib: CP 358774, NSC 718781, OSI 774, R 1415.
2003
3D-QSAR and docking studies on 4-anilinoquinazoline and 4-anilinoquinoline epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors.
2003 Aug
Second-line chemotherapy for non-small cell lung cancer.
2003 Aug
Erlotinib: a new therapeutic approach for non-small cell lung cancer.
2003 Aug
Clinical studies with non-iressa EGFR tyrosine kinase inhibitors.
2003 Aug
The biological and biochemical effects of CP-654577, a selective erbB2 kinase inhibitor, on human breast cancer cells.
2003 Aug 1
Specific method for determination of OSI-774 and its metabolite OSI-420 in human plasma by using liquid chromatography-tandem mass spectrometry.
2003 Aug 15
Tolerability of gefitinib in patients receiving treatment in everyday clinical practice.
2003 Dec
Targeting the epidermal growth factor receptor in non-small cell lung cancer.
2003 Dec 1
For investigational targeted drugs, combination trials pose challenges.
2003 Dec 3
Clinical Trials in Cancer-SMi Conference. 11-12 June 2003, London, UK.
2003 Jul
Pharmacodynamic evaluation of the epidermal growth factor receptor inhibitor OSI-774 in human epidermis of cancer patients.
2003 Jul
Inhibitors of epidermal-growth-factor receptors: a review of clinical research with a focus on non-small-cell lung cancer.
2003 Jul
[Non-small cell lung cancer: 1) Molecular-target therapy].
2003 Jul 10
Research retreat: Pfizer eliminates Sugen, shrinks cancer infrastructure.
2003 Jul 16
Epidermal growth factor receptor inhibitors: an update on their development as cancer therapeutics.
2003 Jun
[Therapeutic implications of epidermal growth factor receptor in lung cancer].
2003 Nov
[Targeting of epidermal growth factor receptor and applications in ORL cancer].
2003 Nov
Identifying predictive and surrogate markers of erlotinib antitumor activity other than rash.
2003 Nov
Can rash associated with HER1/EGFR inhibition be used as a marker of treatment outcome?
2003 Nov
Clinical experience with the HER1/EGFR tyrosine kinase inhibitor erlotinib.
2003 Nov
Erlotinib: preclinical investigations.
2003 Nov
Epidermal growth factor receptor tyrosine kinase inhibitors in late stage clinical trials.
2003 Nov
Pharmacology of oral chemotherapy agents.
2003 Nov-Dec
New targeted therapies in gastrointestinal cancers.
2003 Oct
Receptor-guided alignment-based comparative 3D-QSAR studies of benzylidene malonitrile tyrphostins as EGFR and HER-2 kinase inhibitors.
2003 Oct 23
Liquid-chromatographic determination of erlotinib (OSI-774), an epidermal growth factor receptor tyrosine kinase inhibitor.
2003 Oct 25
Epidermal growth factor receptor inhibitors, gefitinib and erlotinib (Tarceva , OSI-774), in the treatment of bronchioloalveolar carcinoma.
2003 Sep
Gateways to clinical trials.
2003 Sep
Review of epidermal growth factor receptor biology.
2004
Potential role for epidermal growth factor receptor inhibitors in combined-modality therapy for non-small-cell lung cancer.
2004
HER1/EGFR targeting: refining the strategy.
2004
Gateways to clinical trials.
2004 Apr
Epidermal growth factor receptor inhibitors for the treatment of colorectal cancer: a promise fulfilled?
2004 Apr
Epidermal growth factor receptor tyrosine kinase inhibitors: evolving role in the treatment of solid tumors.
2004 Apr
Gefitinib ('Iressa', ZD1839) and new epidermal growth factor receptor inhibitors.
2004 Feb 9
Multicenter phase II study of erlotinib, an oral epidermal growth factor receptor tyrosine kinase inhibitor, in patients with recurrent or metastatic squamous cell cancer of the head and neck.
2004 Jan 1
Synthesis and SAR of potent EGFR/erbB2 dual inhibitors.
2004 Jan 5
Emerging treatments in oncology: focus on tyrosine kinase (erbB) receptor inhibitors.
2004 Jan-Feb
Benzamides and benzamidines as specific inhibitors of epidermal growth factor receptor and v-Src protein tyrosine kinases.
2004 Jul 1
Targeting non-small cell lung cancer with epidermal growth factor tyrosine kinase inhibitors: where do we stand, where do we go.
2004 Jun
EGFR inhibitors square off at ASCO.
2004 Jun
Antitumor activity of erlotinib (OSI-774, Tarceva) alone or in combination in human non-small cell lung cancer tumor xenograft models.
2004 Jun
Epidermal growth factor receptor tyrosine kinase inhibitors.
2004 Jun 14
The role of erlotinib (Tarceva, OSI 774) in the treatment of non-small cell lung cancer.
2004 Jun 15
Emerging role of epidermal growth factor receptor inhibition in therapy for advanced malignancy: focus on NSCLC.
2004 Mar 1
Current data and ongoing trials in patients with recurrent non-small-cell lung cancer.
2004 May
[Lung cancer: molecular targeting therapy].
2004 May
Patents

Patents

20010044451
26
JP2007531525A
6
JP2009519341A
20

Sample Use Guides

In Vivo Use Guide
The dose for NSCLC is 150 mg/day. The dose for pancreatic cancer is 100 mg/day. All doses of TARCEVA should be taken on an empty stomach at least one hour before or two hours after food
Route of Administration: Oral
In Vitro Use Guide
Erlotinib (20 µM) inhibited 33.8% of the growth of T. gondii
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:05:41 UTC 2019
Edited
by admin
on Tue Oct 22 00:05:41 UTC 2019
Record UNII
J4T82NDH7E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ERLOTINIB
EMA EPAR   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
N-(3-ETHYNYLPHENYL)-6,7-BIS(2-METHOXYETHOXY)QUINAZOLIN-4-AMINE
Systematic Name English
CP-358774
Code English
RG-1415
Code English
ERLOTINIB [EMA EPAR]
Common Name English
R-1415
Code English
CP-35877401
Code English
ERLOTINIB [MI]
Common Name English
ERLOTINIB [INN]
Common Name English
ERLOTINIB [VANDF]
Common Name English
4-QUINAZOLINAMINE, N-(3-ETHYNYLPHENYL)-6,7-BIS(2-METHOXYETHOXY)-
Systematic Name English
CP-358,774
Code English
ERLOTINIB [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2167
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
NDF-RT N0000175605
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
WHO-VATC QL01XE03
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
WHO-ATC L01XE03
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
LIVERTOX 365
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
NCI_THESAURUS C129825
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
NDF-RT N0000175076
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
EMA ASSESSMENT REPORTS TARCEVA (AUTHORIZED: PANCREATIC NEOPLASMS)
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
EMA ASSESSMENT REPORTS TARCEVA (AUTHORISED: CARCINOMA, NON-SMALL-CELL LUNG)
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
Code System Code Type Description
DRUG BANK
DB00530
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
PRIMARY
CAS
183321-74-6
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
PRIMARY
ChEMBL
CHEMBL553
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
PRIMARY
IUPHAR
4920
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
PRIMARY
LactMed
183321-74-6
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
PRIMARY
NCI_THESAURUS
C65530
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
PRIMARY
INN
8133
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
PRIMARY
MERCK INDEX
M5000
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
PRIMARY Merck Index
EPA CompTox
183321-74-6
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
PRIMARY
HSDB
183321-74-6
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
PRIMARY
MESH
C400278
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
PRIMARY
WIKIPEDIA
ERLOTINIB
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
PRIMARY
RXCUI
337525
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
PRIMARY RxNorm
EVMPD
SUB16423MIG
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
PRIMARY
PUBCHEM
176870
Created by admin on Tue Oct 22 00:05:41 UTC 2019 , Edited by admin on Tue Oct 22 00:05:41 UTC 2019
PRIMARY
Related Record Type Details
OAT-3
TRANSPORTER -> SUBSTRATE
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> INHIBITOR
Structure of ERLOTINIB HYDROCHLORIDE
SALT/SOLVATE -> PARENT
OAT-2
TRANSPORTER -> SUBSTRATE
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> INHIBITOR
OCT-3
TRANSPORTER -> INHIBITOR
EPIDERMAL GROWTH FACTOR RECEPTOR
TARGET -> INHIBITOR
OCT-1
TRANSPORTER -> SUBSTRATE
OCT-2
TRANSPORTER -> INHIBITOR
OCT-2
TRANSPORTER -> SUBSTRATE
Related Record Type Details
Structure of CP-373413
METABOLITE -> PARENT
MAJOR
FECAL; URINE
Structure of CP-373943
METABOLITE -> PARENT
MAJOR
Structure of CP-457493
METABOLITE -> PARENT
MAJOR
FECAL
Structure of CP-457493
METABOLITE -> PARENT
Structure of CP-373943
METABOLITE -> PARENT
MAJOR
FECAL; URINE
Structure of CP-394356
METABOLITE -> PARENT
Structure of CP-457493
METABOLITE -> PARENT
MAJOR
URINE
Structure of 2-(4-(3-ETHYNYLANILINO)-7-(2-METHOXYETHOXY)QUINAZOLIN-6-YL)OXYACETIC ACID
METABOLITE -> PARENT
MINOR
FECAL; URINE
Structure of CP-394356
METABOLITE -> PARENT
MAJOR
FECAL
Structure of CP-373413
METABOLITE -> PARENT
MAJOR
Related Record Type Details
Structure of ERLOTINIB
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
CSF/PLASMA RATIO BIOLOGICAL SPECIES
BIOLOGICAL
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966