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))
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) [1-2].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Immunopharmacology Comments
Zanubrutinib (BGB-3111) is included in GtoImmuPdb as it acts on B cells, and is a clinical anti-lymphoma drug. BTK inhibition is an established therapeutic modality for the treament of B cell malignancies. BTK inhibitors prevent activation of the B cell antigen receptor (BCR) signalling pathway and promote death of malignant B cells. The developers of zanubrutinib (BeiGene) describe it as being better tolerated than the archetypal BTK inhibitor ibrutinib, with an improved duration of action, better oral bioavailability, refined selectivity and better combinability with ADCC-dependent antibodies (such as rituximab).
Immunopharmacology Disease
Disease X-Refs Comment References
Chronic lymphocytic leukemia Disease Ontology: DOID:1040
OMIM: 151400
Orphanet: ORPHA67038
Phase 3 clinical candidate for CLL and SLL- NCT03336333 will compare BGB-3111 with bendamustine + rituximab.
Waldenstrom macroglobulinemia Disease Ontology: DOID:0050747
OMIM: 153600
Orphanet: ORPHA33226
Phase 3 clinical candidate for WM- NCT03332173 will evaluate clinical efficacy of single agent BGB-3111 in patients with relapsed/refractory WM.
Mantle cell lymphoma Disease Ontology: DOID:0050746
Orphanet: ORPHA52416
Approved drug for MCL (FDA 2019)