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rilzabrutinib   Click here for help

GtoPdb Ligand ID: 9993

Synonyms: Example 31 [WO2014039899] | PRN-1008 | PRN1008 | Wayrilz®
Approved drug PDB Ligand Immunopharmacology Ligand
rilzabrutinib is an approved drug
Compound class: Synthetic organic
Comment: Rilzabrutinib (PRN1008) is an oral, reversible covalent inhibitor of Bruton's tyrosine kinase (BTK) [1]. One possible structure is claimed as Example 31 in Principia Biopharma patent WO2014039899 [2] and this is depicted in PubChem CID 118325989 as the R form without E/Z specification. We show the (E,R) structure here.
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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

rilzabrutinib is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 10
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 138.66
Molecular weight 665.32
XLogP 3.67
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES N#CC(=CC(N1CCN(CC1)C1COC1)(C)C)C(=O)N1CCCC(C1)n1nc(c2c1ncnc2N)c1ccc(cc1F)Oc1ccccc1
Isomeric SMILES N#C/C(=C\C(N1CCN(CC1)C1COC1)(C)C)/C(=O)N1CCC[C@H](C1)n1nc(c2c1ncnc2N)c1ccc(cc1F)Oc1ccccc1
InChI InChI=1S/C36H40FN9O3/c1-36(2,45-15-13-43(14-16-45)26-21-48-22-26)18-24(19-38)35(47)44-12-6-7-25(20-44)46-34-31(33(39)40-23-41-34)32(42-46)29-11-10-28(17-30(29)37)49-27-8-4-3-5-9-27/h3-5,8-11,17-18,23,25-26H,6-7,12-16,20-22H2,1-2H3,(H2,39,40,41)/b24-18+/t25-/m1/s1
InChI Key LCFFREMLXLZNHE-GBOLQPHISA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Langrish CL, Bradshaw JM, Owens TD, Campbell RL, Francesco MR, Karr DE, Murray SK, Quesenberry RC, Smith PF, Taylor MD et al.. (2017)
PRN1008, a Reversible Covalent BTK Inhibitor in Clinical Development for Immune Thrombocytopenic Purpura.
Blood, 130: 1052 Meeting poster. DOI: 10.1182/blood.V130.Suppl_1.1052.1052
2. Owens T, Verner E. (2014)
PYRAZOLOPYRIMIDINE COMPOUNDS AS KINASE INHIBITORS.
Patent number: WO2014039899. Assignee: Principia Biopharma. Priority date: 06/09/2013. Publication date: 13/03/2014.
3. Smith PF, Krishnarajah J, Nunn PA, Hill RJ, Karr D, Tam D, Masjedizadeh M, Funk JO, Gourlay SG. (2017)
A phase I trial of PRN1008, a novel reversible covalent inhibitor of Bruton's tyrosine kinase, in healthy volunteers.
Br J Clin Pharmacol, 83 (11): 2367-2376. [PMID:28636208]