venetoclax   

GtoPdb Ligand ID: 8318

Synonyms: ABT-199 | GDC-0199 | Venclexta® | Venclyxto®
venetoclax is an approved drug (FDA and EMA (2016))
Compound class: Synthetic organic
Comment: Venetoclax is a BH3 mimetic that selectively targets Bcl-2 [4], utilised for its pro-apoptotic activity. It is noteworthy that venetoclax is the first approved medicine designed to induce a natural process that helps cells self-destruct.
The IUPAC name provided by PubChem matches 'Example 5' claimed in patent US8580794 [1].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 14
Topological polar surface area 180.41
Molecular weight 867.32
XLogP 9.38
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES Clc1ccc(cc1)C1=C(CCC(C1)(C)C)CN1CCN(CC1)c1ccc(c(c1)Oc1cnc2c(c1)cc[nH]2)C(=O)NS(=O)(=O)c1ccc(c(c1)[N+](=O)[O-])NCC1CCOCC1
Isomeric SMILES Clc1ccc(cc1)C1=C(CCC(C1)(C)C)CN1CCN(CC1)c1ccc(c(c1)Oc1cnc2c(c1)cc[nH]2)C(=O)NS(=O)(=O)c1ccc(c(c1)[N+](=O)[O-])NCC1CCOCC1
InChI InChI=1S/C45H50ClN7O7S/c1-45(2)15-11-33(39(26-45)31-3-5-34(46)6-4-31)29-51-17-19-52(20-18-51)35-7-9-38(42(24-35)60-36-23-32-12-16-47-43(32)49-28-36)44(54)50-61(57,58)37-8-10-40(41(25-37)53(55)56)48-27-30-13-21-59-22-14-30/h3-10,12,16,23-25,28,30,48H,11,13-15,17-22,26-27,29H2,1-2H3,(H,47,49)(H,50,54)
InChI Key LQBVNQSMGBZMKD-UHFFFAOYSA-N
Immunopharmacology Comments
Bcl-2, is an antiapoptotic protein that is central to the survival of chronic lymphocytic leukemia cells in which it is often pathologically overexpressed. Venetoclax inhibits this antiapoptotic functionality and restores apoptotic balance, which leads to tumour cell death.
Immunopharmacology Disease
Disease X-Refs Comment References
Asthma Disease Ontology: DOID:2841
OMIM: 600807
Venetoclax (ABT-199) has been shown to induce apoptosis of airway inflammatory cells (eosinophils, neutrophils, Th2, Th17 and dendritic cells) suggesting a potiential role in management of eosinophilic or corticosteroid resistant-neutrophilic airway inflammation. 5
Chronic lymphocytic leukemia Disease Ontology: DOID:1040
OMIM: 151400
Orphanet: ORPHA67038
Approved drug for CLL with or without 17p deletion. 2