tucatinib   Click here for help

GtoPdb Ligand ID: 9922

Synonyms: ARRY-380 | Example 11 [WO2007059257A2] | ONT-380 | Tukysa®
Approved drug
tucatinib is an approved drug (FDA (2020))
Compound class: Synthetic organic
Comment: Tucatinib is an orally bioavailable ERBB2 (HER2) receptor tyrosine kinase inhibitor that was developed as a novel antineoplastic agent by Seattle Genetics [2]. The chemical structure is claimed as Example 11 in Array Biopharma patent WO2007059257A2 [3], and was exemplified as ARRY-380 in the later patent WO2013056183A1 [1]. Tucatinib contains a quinazoline core that is conserved in other tyrosine kinase inhibitors including lapatinib, erlotinib, and gefitinib [2].
The INN tucatinib replaced the earlier INN irbinitinib that was associated with this chemical entity.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 110.85
Molecular weight 480.2
XLogP 3.75
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Cc1cc(ccc1Oc1ccn2c(c1)ncn2)Nc1ncnc2c1cc(cc2)NC1=NC(CO1)(C)C
Isomeric SMILES Cc1cc(ccc1Oc1ccn2c(c1)ncn2)Nc1ncnc2c1cc(cc2)NC1=NC(CO1)(C)C
InChI InChI=1S/C26H24N8O2/c1-16-10-17(5-7-22(16)36-19-8-9-34-23(12-19)28-15-30-34)31-24-20-11-18(4-6-21(20)27-14-29-24)32-25-33-26(2,3)13-35-25/h4-12,14-15H,13H2,1-3H3,(H,32,33)(H,27,29,31)
InChI Key SDEAXTCZPQIFQM-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2020))
International Nonproprietary Names Click here for help
INN number INN
9997 tucatinib
Synonyms Click here for help
ARRY-380 | Example 11 [WO2007059257A2] | ONT-380 | Tukysa®
Database Links Click here for help
CAS Registry No. 937263-43-9 (source: WHO INN record)
DrugCentral Ligand 5389
GtoPdb PubChem SID 363894216
PubChem CID 51039094
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