osimertinib

Ligand id: 7719

Name: osimertinib

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Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 87.55
Molecular weight 499.27
XLogP 3.44
No. Lipinski's rules broken 1

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2015), EMA (2016))
IUPAC Name
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
INN number INN
10043 osimertinib
Synonyms
AZD 9291 | AZD-9291 | AZD9291 | mereletinib (obsolete INN) | Tagrisso®
Database Links
CAS Registry No. 1421373-65-0
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
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Search UniChem for chemical match using the InChIKey DUYJMQONPNNFPI-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone DUYJMQONPNNFPI
Comments
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 [4,7] 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) [6] and Ou and Soo (2015) [3].