brigatinib   Click here for help

GtoPdb Ligand ID: 7741

Synonyms: Alunbrig® | AP-26113 | AP26113 | compound 11q [PMID: 27144831]
Approved drug PDB Ligand
brigatinib is an approved drug (FDA (2017), EMA (2018))
Compound class: Synthetic organic
Comment: Brigatinib (AP26113) is a phosphine oxide-containing drug developed as a treatment for cancers driven by anaplastic lymphoma kinase (ALK) rearrangements [1] or by T790M gatekeeper mutant EGFR. It is an orally available inhibitor.
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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 8
Topological polar surface area 95.67
Molecular weight 583.26
XLogP 5.11
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES COc1cc(ccc1Nc1ncc(c(n1)Nc1ccccc1P(=O)(C)C)Cl)N1CCC(CC1)N1CCN(CC1)C
Isomeric SMILES COc1cc(ccc1Nc1ncc(c(n1)Nc1ccccc1P(=O)(C)C)Cl)N1CCC(CC1)N1CCN(CC1)C
InChI InChI=1S/C29H39ClN7O2P/c1-35-15-17-37(18-16-35)21-11-13-36(14-12-21)22-9-10-24(26(19-22)39-2)33-29-31-20-23(30)28(34-29)32-25-7-5-6-8-27(25)40(3,4)38/h5-10,19-21H,11-18H2,1-4H3,(H2,31,32,33,34)
InChI Key AILRADAXUVEEIR-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2017), EMA (2018))
IUPAC Name Click here for help
5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-[2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]pyrimidine-2,4-diamine
International Nonproprietary Names Click here for help
INN number INN
10085 brigatinib
Synonyms Click here for help
Alunbrig® | AP-26113 | AP26113 | compound 11q [PMID: 27144831]
Database Links Click here for help
BindingDB Ligand 50185140
CAS Registry No. 1197953-54-0 (source: WHO INN record)
ChEMBL Ligand CHEMBL3545311
DrugBank Ligand DB12267
GtoPdb PubChem SID 223366074
PubChem CID 68165256
RCSB PDB Ligand 6GY
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SynPHARM 80282 (in complex with anaplastic lymphoma receptor tyrosine kinase)
80285 (in complex with anaplastic lymphoma receptor tyrosine kinase)