zanubrutinib   Click here for help

GtoPdb Ligand ID: 9861

Synonyms: BGB-3111 | BGB3111 | Brukinsa® | compound 27b [US9447106]
Approved drug Immunopharmacology Ligand
zanubrutinib is an approved drug (FDA (2019), EMA (2021))
Compound class: Synthetic organic
Comment: Zanubrutinib (BGB-3111) is a potent, selective and irreversible BTK inhibitor that was developed by BeiGene for utility in the treatment of B cell cancers, such as non-Hodgkin's lymphoma and chronic lymphocytic leukemia (CLL) [1,4].
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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
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 6
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 102.48
Molecular weight 471.23
XLogP 4.5
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)N1CCC(CC1)[C@@H]1CCNc2n1nc(c2C(=O)N)c1ccc(cc1)Oc1ccccc1
Isomeric SMILES C=CC(=O)N1CCC(CC1)[C@@H]1CCNc2n1nc(c2C(=O)N)c1ccc(cc1)Oc1ccccc1
InChI InChI=1S/C27H29N5O3/c1-2-23(33)31-16-13-18(14-17-31)22-12-15-29-27-24(26(28)34)25(30-32(22)27)19-8-10-21(11-9-19)35-20-6-4-3-5-7-20/h2-11,18,22,29H,1,12-17H2,(H2,28,34)/t22-/m0/s1
InChI Key RNOAOAWBMHREKO-QFIPXVFZSA-N
No information available.
Summary of Clinical Use Click here for help
Zanubrutinib was evaluated for efficacy in a large number of clinical trials, across a range of hematological cancers. Click here to link to ClinicalTrials.gov's full list of zanubrutinib/BGB-3111 studies.
The FDA first approved zanubrutinib in November 2019 for the treatment of mantle cell lymphoma (MCL; in adult patients who have received at least one prior therapy). In June 2020, the drug was approved in China for the treatment of adult patients with CLL/SLL who have received at least one prior therapy, and for patients with MCL who have received at least one prior therapy. In the EU, zanubrutinib holds orphan designation for lymphoplasmacytic lymphoma, which was granted in May 2019. In April 2021, the The FDA accepted a supplemental new drug application (sNDA) for zanubrutinib for the treatment of adults with Waldenström macroglobulinemia, and approval followed in August that year. FDA approval was expanded in early 2023, to include treatment of CLL, based on evidence from the phase 3 SEQUOIA study (NCT03336333) [2-3]. A further expansion by the FDA in March 2024 added the treatment of relapsed/refractory follicular lymphoma to zanubrutinib's indication list.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03053440 A Study Comparing BGB-3111 and Ibrutinib in Participants With Waldenström's Macroglobulinemia (WM) Phase 3 Interventional BeiGene
NCT03332173 Study of BTK Inhibitor BGB-3111 in Chinese Participants With Relapsed/Refractory Waldenström's Macroglobulinemia (WM) Phase 2 Interventional BeiGene
NCT03336333 A Study Comparing Zanubrutinib With Bendamustine Plus Rituximab in Participants With Previously Untreated CLL or SLL Phase 3 Interventional BeiGene