ZANUBRUTINIB

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H29N5O3
Molecular Weight	471.5509
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)C1=C2NCC[C@@H](C3CCN(CC3)C(=O)C=C)N2N=C1C4=CC=C(OC5=CC=CC=C5)C=C4

InChI

InChIKey=RNOAOAWBMHREKO-QFIPXVFZSA-N

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

HIDE SMILES / InChI

Molecular Formula	C27H29N5O3
Molecular Weight	471.5509
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/213217s000lbl.pdf| https://pubmed.ncbi.nlm.nih.gov/31381333

Zanubrutinib (formerly known as BGB-3111) was developed by BeiGene as a small-molecule inhibitor of Bruton's tyrosine kinase (BTK). The drug forms a covalent bond with a cysteine residue in the BTK active site, leading to inhibition of BTK activity. BTK signaling results in activation of pathways necessary for B-cell proliferation, trafficking, chemotaxis, and adhesion, thus Zanubrutinib inhibits malignant B-cell proliferation and reduces tumor growth. Zanubrutinib was granted accelerated approval by the FDA in November 2019 based on clinical trial results that demonstrated an 84% overall response rate from zanubrutinib therapy in patients with mantle cell lymphoma (MCL). On August 31, 2021, the Food and Drug Administration approved zanubrutinib for adult patients with Waldenström’s macroglobulinemia (WM).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tyrosine-protein kinase BTK 24 Target ID: Q06187 Gene ID: 695.0 Gene Symbol: BTK Target Organism: Homo sapiens (Human) Sources: https://pubmed.ncbi.nlm.nih.gov/31381333/	Inhibitor 8297		0.3 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
mantle cell lymphoma 5 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/213217s000lbl.pdf	Primary		Approved 8429	BRUKINSA Approved Use indicated for the treatment of adult patients with mantle cell lymphoma (MCL) who have received at least one prior therapy
Waldenström’s macroglobulinemia 1 Sources: https://www.fda.gov/drugs/resources-information-approved-drugs/fda-approves-zanubrutinib-waldenstroms-macroglobulinemia	Primary		Approved 8429	Brukinsa Approved Use zanubrutinib (Brukinsa, BeiGene) for adult patients with Waldenström’s macroglobulinemia Launch Date 2021

Sample Use Guides

In Vivo Use Guide

160 mg orally twice daily or 320 mg orally once daily; swallow whole with water and with or without food

Route of Administration: Oral

In Vitro Use Guide

The in vitro cell-based activity of zanubrutinib on BTK was evaluated in mantle cell lymphoma (MCL) cell lines and showed that BTK was inhibited with an IC50 of 1.8 nM. In vitro activity was evaluated on a panel of 23 hematologic cancer cell lines. Zanubrutinib demonstrated the most prominent growth inhibitory activity on 3 MCL cell lines and a diffuse large B-cell lymphoma (DLBCL) cell line.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:53:49 GMT 2023` Edited by `admin` on `Sat Dec 16 10:53:49 GMT 2023`
Record UNII	AG9MHG098Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ZANUBRUTINIB

Official Name

English

PYRAZOLO(1,5-A)PYRIMIDINE-3-CARBOXAMIDE, 4,5,6,7-TETRAHYDRO-7-(1-(1-OXO-2-PROPEN-1-YL)-4-PIPERIDINYL)-2-(4-PHENOXYPHENYL)-, (7S)-

Systematic Name

English

ZANUBRUTINIB [USAN]

Common Name

English

BRUKINSA

Brand Name

English

BGB-3111

Code

English

(7S)-2-(4-Phenoxyphenyl)-7-[1-(prop-2-enoyl)piperidin-4-yl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide

Systematic Name

English

ZANUBRUTINIB [MI]

Common Name

English

ZANUBRUTINIB [ORANGE BOOK]

Common Name

English

Zanubrutinib [WHO-DD]

Common Name

English

zanubrutinib [INN]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

757020