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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2D Structure
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Physico-chemical Properties
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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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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 Model List of Essential Medicines (21st List, 2019). Access PDF version.
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
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
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SynPHARM 81179 (in complex with epidermal growth factor receptor)
79526 (in complex with epidermal growth factor receptor)
Wikipedia Erlotinib