osimertinib   Click here for help

GtoPdb Ligand ID: 7719

Synonyms: AZD 9291 | AZD-9291 | AZD9291 | mereletinib (obsolete INN) | Tagrisso®
Approved drug PDB Ligand
osimertinib is an approved drug (FDA (2015), EMA (2016))
Compound class: Synthetic organic
Comment: Osimertinib (AZD9291) is a third-generation, potent, selective and irreversible inhibitor of the epidermal growth factor receptor (EGFR) tyrosine kinase bearing mutations which either sensitise the receptor, or cause drug resistance (eg the T790M mutation) [2]. The compound is less effective against the wild-type receptor.
This compound is included in AstaZeneca's Open Innovation Pharmacology Toolbox. There are reports of acquired resistance to osimertinib with tumours developing the C797S [6,9] and L718Q mutations [1] .

Third-generation mutant EGFR inhibitors are being developed to circumvent dose-limiting WT EGFR-driven toxicities such as gastrointestinal toxicity and rash. The progress being made in developing advanced generation EGFR inhibitors is discussed by Yu and Riely (2013) [8] and Ou and Soo (2015) [4].
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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: osimertinib

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 7
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 87.55
Molecular weight 499.27
XLogP 3.6
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 C=CC(=O)Nc1cc(Nc2nccc(n2)c2cn(c3c2cccc3)C)c(cc1N(CCN(C)C)C)OC
Isomeric SMILES C=CC(=O)Nc1cc(Nc2nccc(n2)c2cn(c3c2cccc3)C)c(cc1N(CCN(C)C)C)OC
InChI InChI=1S/C28H33N7O2/c1-7-27(36)30-22-16-23(26(37-6)17-25(22)34(4)15-14-33(2)3)32-28-29-13-12-21(31-28)20-18-35(5)24-11-9-8-10-19(20)24/h7-13,16-18H,1,14-15H2,2-6H3,(H,30,36)(H,29,31,32)
InChI Key DUYJMQONPNNFPI-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2015), EMA (2016))
IUPAC Name Click here for help
N-[2-[2-(dimethylamino)ethyl-methylamino]-4-methoxy-5-[[4-(1-methylindol-3-yl)pyrimidin-2-yl]amino]phenyl]prop-2-enamide
International Nonproprietary Names Click here for help
INN number INN
10043 osimertinib
Synonyms Click here for help
AZD 9291 | AZD-9291 | AZD9291 | mereletinib (obsolete INN) | Tagrisso®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9649872
Reactome Reaction Reactome logo R-HSA-9665121, R-HSA-9665280
Other databases
CAS Registry No. 1421373-65-0
DrugCentral Ligand 5062
GtoPdb PubChem SID 223366052
PubChem CID 71496458
RCSB PDB Ligand YY3
Search Google for chemical match using the InChIKey DUYJMQONPNNFPI-UHFFFAOYSA-N
Search Google for chemicals with the same backbone DUYJMQONPNNFPI
Search PubMed clinical trials osimertinib
Search PubMed titles osimertinib
Search PubMed titles/abstracts osimertinib
UniChem Compound Search for chemical match using the InChIKey DUYJMQONPNNFPI-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey DUYJMQONPNNFPI-UHFFFAOYSA-N