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

Details

Stereochemistry ACHIRAL
Molecular Formula C22H23N3O4.ClH
Molecular Weight 429.897
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ERLOTINIB HYDROCHLORIDE

SMILES

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

InChI

InChIKey=GTTBEUCJPZQMDZ-UHFFFAOYSA-N
InChI=1S/C22H23N3O4.ClH/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);1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C22H23N3O4
Molecular Weight 393.4357
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021743s14s16lbl.pdf

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TARCEVA

Approved Use

TARCEVA is a kinase inhibitor indicated for: Maintenance treatment of patients with locally advanced or metastatic non-small cell lung cancer (NSCLC) whose disease has not progressed after four cycles of platinum-based first-line chemotherapy. Treatment of locally advanced or metastatic non-small cell lung cancer after failure of at least one prior chemotherapy regimen. First-line treatment of patients with locally advanced, unresectable or metastatic pancreatic cancer, in combination with gemcitabine.

Launch Date

2004
Primary
TARCEVA

Approved Use

TARCEVA is a kinase inhibitor indicated for: Maintenance treatment of patients with locally advanced or metastatic non-small cell lung cancer (NSCLC) whose disease has not progressed after four cycles of platinum-based first-line chemotherapy. Treatment of locally advanced or metastatic non-small cell lung cancer after failure of at least one prior chemotherapy regimen. First-line treatment of patients with locally advanced, unresectable or metastatic pancreatic cancer, in combination with gemcitabine.

Launch Date

2004
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1969.5 ng/mL
85 mg/m^2 1 times / day steady, oral
dose: 85 mg/m^2
route of administration: oral
experiment type: steady
co-administered:
ERLOTINIB plasma
Homo sapiens
population: unhealthy
age: Children
sex: UNKNOWN
food status: UNKNOWN
4.07 μg/mL
100 mg single, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ERLOTINIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.25 μg/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERLOTINIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1108.89 ng/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERLOTINIB HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.09 μg/mL
150 mg 1 times / day multiple, oral
dose: 150 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ERLOTINIB HYDROCHLORIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
26716.7 ng*h/mL
85 mg/m^2 1 times / day steady, oral
dose: 85 mg/m^2
route of administration: oral
experiment type: steady
co-administered:
ERLOTINIB plasma
Homo sapiens
population: unhealthy
age: Children
sex: UNKNOWN
food status: UNKNOWN
32 μg × h/mL
100 mg single, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ERLOTINIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
29.9 μg × h/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERLOTINIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
25489.41 ng × h/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERLOTINIB HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
15.2 μg × h/mL
150 mg 1 times / day multiple, oral
dose: 150 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ERLOTINIB HYDROCHLORIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
12.4 h
100 mg single, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ERLOTINIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
14.4 h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERLOTINIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
36.2 h
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERLOTINIB HYDROCHLORIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
14.33 h
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERLOTINIB HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
14.75 h
150 mg 1 times / day multiple, oral
dose: 150 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ERLOTINIB HYDROCHLORIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
7%
ERLOTINIB plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
7%
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERLOTINIB HYDROCHLORIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
OverviewDrug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major [Km 5.9 uM]
yes (co-administration study)
Comment: Coadministration of erlotinib with ketoconazole, a potent inhibitor of CYP3A4, resulted in a significant (67%) increase in erlotinib exposure (Study NP16612). The CYP3A4 inducer rifampicin has been demonstrated to impact the exposure to erlotinib; in Study NP16638 co-administration led to a 64% reduction in erlotinib AUC.
Page: -
minor
no
no
no
yes [Km 24 uM]
yes
yes
yes
Tox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
Benzamides and benzamidines as specific inhibitors of epidermal growth factor receptor and v-Src protein tyrosine kinases.
2004-07-01
The role of erlotinib (Tarceva, OSI 774) in the treatment of non-small cell lung cancer.
2004-06-15
Epidermal growth factor receptor tyrosine kinase inhibitors.
2004-06-14
Targeting non-small cell lung cancer with epidermal growth factor tyrosine kinase inhibitors: where do we stand, where do we go.
2004-06
EGFR inhibitors square off at ASCO.
2004-06
Antitumor activity of erlotinib (OSI-774, Tarceva) alone or in combination in human non-small cell lung cancer tumor xenograft models.
2004-06
Combination treatment of glioblastoma multiforme cell lines with the anti-malarial artesunate and the epidermal growth factor receptor tyrosine kinase inhibitor OSI-774.
2004-05-01
Current data and ongoing trials in patients with recurrent non-small-cell lung cancer.
2004-05
[Lung cancer: molecular targeting therapy].
2004-05
New cytotoxic and molecular-targeted therapies of head and neck tumors.
2004-05
Identification of epidermal growth factor receptor-derived peptides immunogenic for HLA-A2(+) cancer patients.
2004-04-19
Gateways to clinical trials.
2004-04
Epidermal growth factor receptor inhibitors for the treatment of colorectal cancer: a promise fulfilled?
2004-04
Epidermal growth factor receptor tyrosine kinase inhibitors: evolving role in the treatment of solid tumors.
2004-04
Rationale and clinical validation of epidermal growth factor receptor as a target in the treatment of head and neck cancer.
2004-04
Emerging role of epidermal growth factor receptor inhibition in therapy for advanced malignancy: focus on NSCLC.
2004-03-01
The HER receptor family: a rich target for therapeutic development.
2004-03-01
The role of EGFR inhibitors in nonsmall cell lung cancer.
2004-03
[Bronchioloalveolar carcinoma (BAC)].
2004-03
Inverse correlation of epidermal growth factor receptor messenger RNA induction and suppression of anchorage-independent growth by OSI-774, an epidermal growth factor receptor tyrosine kinase inhibitor, in glioblastoma multiforme cell lines.
2004-03
Gateways to clinical trials.
2004-02-28
Emerging treatments in oncology: focus on tyrosine kinase (erbB) receptor inhibitors.
2004-02-18
Gefitinib ('Iressa', ZD1839) and new epidermal growth factor receptor inhibitors.
2004-02-09
Novel treatments in non-small cell lung cancer.
2004-02
Pharmacology of oral chemotherapy agents.
2004-01-07
Synthesis and SAR of potent EGFR/erbB2 dual inhibitors.
2004-01-05
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.
2004-01-01
Lung cancer: looking ahead in 2004.
2004-01
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
Emerging roles of targeted small molecule protein-tyrosine kinase inhibitors in cancer therapy.
2004
HER1/EGFR targeting: refining the strategy.
2004
Distribution and function of EGFR in human tissue and the effect of EGFR tyrosine kinase inhibition.
2003-12-12
For investigational targeted drugs, combination trials pose challenges.
2003-12-03
Targeting the epidermal growth factor receptor in non-small cell lung cancer.
2003-12-01
Epidermal growth factor receptor tyrosine kinase inhibitors: application in non-small cell lung cancer.
2003-12
Tolerability of gefitinib in patients receiving treatment in everyday clinical practice.
2003-12
[Therapeutic implications of epidermal growth factor receptor in lung cancer].
2003-11
[Inhibitors of epidermal growth factor receptor and colorectal cancer].
2003-11
[Targeting of epidermal growth factor receptor and applications in ORL cancer].
2003-11
Identifying predictive and surrogate markers of erlotinib antitumor activity other than rash.
2003-11
Can rash associated with HER1/EGFR inhibition be used as a marker of treatment outcome?
2003-11
Clinical experience with the HER1/EGFR tyrosine kinase inhibitor erlotinib.
2003-11
Erlotinib: preclinical investigations.
2003-11
Targeting the HER1/EGFR receptor to improve outcomes in non-small-cell lung cancer.
2003-11
Epidermal growth factor receptor tyrosine kinase inhibitors in late stage clinical trials.
2003-11
Defining the role of the epidermal growth factor receptor in pancreatic cancer grown in vitro.
2003-11
Gateways to clinical trials.
2003-10
3D-QSAR and docking studies on 4-anilinoquinazoline and 4-anilinoquinoline epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors.
2003-08
Small-molecule epidermal growth factor receptor tyrosine kinase inhibitors.
2003
Patents

Sample Use Guides

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
Erlotinib (20 µM) inhibited 33.8% of the growth of T. gondii
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:00:05 GMT 2025
Edited
by admin
on Mon Mar 31 18:00:05 GMT 2025
Record UNII
DA87705X9K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TARCEVA
Preferred Name English
ERLOTINIB HYDROCHLORIDE
JAN   MART.   MI   ORANGE BOOK   USAN   WHO-DD  
USAN  
Official Name English
4-(M-ETHYNYLANILINO)-6,7-BIS(2-METHOXYETHOXY)QUINAZOLINE MONOHYDROCHLORIDE
Systematic Name English
Erlotinib hydrochloride [WHO-DD]
Common Name English
ERLOTINIB HYDROCHLORIDE [MART.]
Common Name English
ERLOTINIB HYDROCHLORIDE [USP-RS]
Common Name English
OSI-774
Code English
N-(3-ETHENYLPHENYL)-6,7-BIS(2-METHOXYETHOXY)-4-QUINAZOLINAMINE HYDROCHLORIDE
Systematic Name English
ERLOTINIB HYDROCHLORIDE [MI]
Common Name English
ERLOTINIB HYDROCHLORIDE [ORANGE BOOK]
Common Name English
ERLOTINIB HYDROCHLORIDE [USAN]
Common Name English
ERLOTINIB HYDROCHLORIDE [JAN]
Common Name English
ERLOTINIB HCL
Common Name English
CP-358774-01
Code English
CP-358,774-01
Code English
4-QUINAZOLINAMINE, N-(3-ETHYNYLPHENYL)-6,7-BIS(2-METHOXYETHOXY)-, MONOHYDROCHLORIDE
Common Name English
CP-358
Code English
Classification Tree Code System Code
NCI_THESAURUS C2167
Created by admin on Mon Mar 31 18:00:05 GMT 2025 , Edited by admin on Mon Mar 31 18:00:05 GMT 2025
EMA ASSESSMENT REPORTS TARCEVA (AUTHORIZED: PANCREATIC NEOPLASMS)
Created by admin on Mon Mar 31 18:00:05 GMT 2025 , Edited by admin on Mon Mar 31 18:00:05 GMT 2025
NCI_THESAURUS C129825
Created by admin on Mon Mar 31 18:00:05 GMT 2025 , Edited by admin on Mon Mar 31 18:00:05 GMT 2025
FDA ORPHAN DRUG 172003
Created by admin on Mon Mar 31 18:00:05 GMT 2025 , Edited by admin on Mon Mar 31 18:00:05 GMT 2025
Code System Code Type Description
CHEBI
53509
Created by admin on Mon Mar 31 18:00:05 GMT 2025 , Edited by admin on Mon Mar 31 18:00:05 GMT 2025
PRIMARY
ChEMBL
CHEMBL553
Created by admin on Mon Mar 31 18:00:05 GMT 2025 , Edited by admin on Mon Mar 31 18:00:05 GMT 2025
PRIMARY
RXCUI
477320
Created by admin on Mon Mar 31 18:00:05 GMT 2025 , Edited by admin on Mon Mar 31 18:00:05 GMT 2025
PRIMARY RxNorm
MERCK INDEX
m5000
Created by admin on Mon Mar 31 18:00:05 GMT 2025 , Edited by admin on Mon Mar 31 18:00:05 GMT 2025
PRIMARY Merck Index
DRUG BANK
DBSALT000064
Created by admin on Mon Mar 31 18:00:05 GMT 2025 , Edited by admin on Mon Mar 31 18:00:05 GMT 2025
PRIMARY
EVMPD
SUB21050
Created by admin on Mon Mar 31 18:00:05 GMT 2025 , Edited by admin on Mon Mar 31 18:00:05 GMT 2025
PRIMARY
EPA CompTox
DTXSID10171412
Created by admin on Mon Mar 31 18:00:05 GMT 2025 , Edited by admin on Mon Mar 31 18:00:05 GMT 2025
PRIMARY
DAILYMED
DA87705X9K
Created by admin on Mon Mar 31 18:00:05 GMT 2025 , Edited by admin on Mon Mar 31 18:00:05 GMT 2025
PRIMARY
SMS_ID
100000092747
Created by admin on Mon Mar 31 18:00:05 GMT 2025 , Edited by admin on Mon Mar 31 18:00:05 GMT 2025
PRIMARY
USAN
MM-14
Created by admin on Mon Mar 31 18:00:05 GMT 2025 , Edited by admin on Mon Mar 31 18:00:05 GMT 2025
PRIMARY
CAS
183319-69-9
Created by admin on Mon Mar 31 18:00:05 GMT 2025 , Edited by admin on Mon Mar 31 18:00:05 GMT 2025
PRIMARY
NCI_THESAURUS
C2693
Created by admin on Mon Mar 31 18:00:05 GMT 2025 , Edited by admin on Mon Mar 31 18:00:05 GMT 2025
PRIMARY
PUBCHEM
176871
Created by admin on Mon Mar 31 18:00:05 GMT 2025 , Edited by admin on Mon Mar 31 18:00:05 GMT 2025
PRIMARY
FDA UNII
DA87705X9K
Created by admin on Mon Mar 31 18:00:05 GMT 2025 , Edited by admin on Mon Mar 31 18:00:05 GMT 2025
PRIMARY
RS_ITEM_NUM
1241608
Created by admin on Mon Mar 31 18:00:05 GMT 2025 , Edited by admin on Mon Mar 31 18:00:05 GMT 2025
PRIMARY
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