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Details

Stereochemistry ACHIRAL
Molecular Formula C22H23N3O4
Molecular Weight 393.4357
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ERLOTINIB

SMILES

COCCOC1=CC2=C(C=C1OCCOC)C(NC3=CC(=CC=C3)C#C)=NC=N2

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

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

Targets

Primary TargetPharmacologyConditionPotency
1.2 nM [IC50]
2.23 µM [IC50]
0.02 µM [IC50]
0.08 µM [IC50]
0.05 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TARCEVA
Primary
TARCEVA

Cmax

ValueDoseCo-administeredAnalytePopulation
1.25 μg/mL
100 mg single, oral
ERLOTINIB plasma
Homo sapiens
4.07 μg/mL
100 mg single, intravenous
ERLOTINIB plasma
Homo sapiens
1969.5 ng/mL
85 mg/m^2 1 times / day steady, oral
ERLOTINIB plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
29.9 μg × h/mL
100 mg single, oral
ERLOTINIB plasma
Homo sapiens
32 μg × h/mL
100 mg single, intravenous
ERLOTINIB plasma
Homo sapiens
26716.7 ng*h/mL
85 mg/m^2 1 times / day steady, oral
ERLOTINIB plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
14.4 h
100 mg single, oral
ERLOTINIB plasma
Homo sapiens
12.4 h
100 mg single, intravenous
ERLOTINIB plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
7%
ERLOTINIB plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

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