rilzabrutinib   Click here for help

GtoPdb Ligand ID: 9993

Synonyms: Example 31 [WO2014039899] | PRN-1008 | PRN1008
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Rilzabrutinib (PRN1008) is an oral, reversible covalent inhibitor of Bruton's tyrosine kinase (BTK) [1]. The chemical structure of PRN1008 has not been formally disclosed, and there is some uncertainty of its precise stereochemistry evident in online resources. 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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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(E)-2-[(3R)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile
International Nonproprietary Names Click here for help
INN number INN
10966 rilzabrutinib
Synonyms Click here for help
Example 31 [WO2014039899] | PRN-1008 | PRN1008
Database Links Click here for help
BindingDB Ligand 143212
CAS Registry No. 1575596-29-0 (source: PubChem)
ChEMBL Ligand CHEMBL3702854
GtoPdb PubChem SID 374883880
PubChem CID 73388818
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UniChem Compound Search for chemical match using the InChIKey LCFFREMLXLZNHE-GBOLQPHISA-N
UniChem Connectivity Search for chemical match using the InChIKey LCFFREMLXLZNHE-GBOLQPHISA-N