erlotinib   Click here for help

GtoPdb Ligand ID: 4920

Synonyms: NSC 718781 | OSI 744 | OSI-774 | R 1415 | Tarceva®
Approved drug PDB Ligand
erlotinib is an approved drug (FDA (2004), EMA (2005))
Compound class: Synthetic organic
Comment: Erlotinib is a clinically approved type-1 inhibitor of the epidermal growth factor receptor (EGFR) receptor tyrosine kinase. This drug shows some selectivity for EGFR exon 19 deletion or exon 21 L858R mutations over the wild type receptor.
Subsequent studies have shown erlotinib to be a potent inhibitor of JAK2V617F activity. JAK2V617F, a mutant from 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. Study suggests that erlotinib may be used for treatment of JAK2V617F-positive PV and other myeloproliferative disorders. Specificity of inhibition with regard to other tyrosine kinase receptors remains to be fully characterized. Erlotinib is a Type-1 kinase inhibitor.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: erlotinib

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 10
Topological polar surface area 74.73
Molecular weight 393.17
XLogP 2.7
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES COCCOc1cc2c(ncnc2cc1OCCOC)Nc1cccc(c1)C#C
Isomeric SMILES COCCOc1cc2c(ncnc2cc1OCCOC)Nc1cccc(c1)C#C
InChI 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)
InChI Key AAKJLRGGTJKAMG-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2004), EMA (2005))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine
International Nonproprietary Names Click here for help
INN number INN
8133 erlotinib
Synonyms Click here for help
NSC 718781 | OSI 744 | OSI-774 | R 1415 | Tarceva®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-1173285
Reactome Reaction Reactome logo R-HSA-1220610
Other databases
CAS Registry No. 183321-74-6
ChEBI CHEBI:114785
ChEMBL Ligand CHEMBL553
DrugBank Ligand DB00530
DrugCentral Ligand 1045
GtoPdb PubChem SID 178101619
PubChem CID 176870
RCSB PDB Ligand AQ4
Search Google for chemical match using the InChIKey AAKJLRGGTJKAMG-UHFFFAOYSA-N
Search Google for chemicals with the same backbone AAKJLRGGTJKAMG
Search PubMed clinical trials erlotinib
Search PubMed titles erlotinib
Search PubMed titles/abstracts erlotinib
SynPHARM 81179 (in complex with epidermal growth factor receptor)
79526 (in complex with epidermal growth factor receptor)
UniChem Compound Search for chemical match using the InChIKey AAKJLRGGTJKAMG-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey AAKJLRGGTJKAMG-UHFFFAOYSA-N
Wikipedia Erlotinib