LB42908   Click here for help

GtoPdb Ligand ID: 8028

Synonyms: LB 42908
Compound class: Synthetic organic
Comment: The discovery of LB42908 is described in [2], where it is compound 2. LB42908 is a highly potent, selective, and non-peptidic farnesyltransferase inhibitor (FTI). LB42908 does not appear to have progressed beyond preclinical investigation.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 64.76
Molecular weight 535.26
XLogP 3.59
No. Lipinski's rules broken 0
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Canonical SMILES CN1CCN(CC1)C(=O)c1cn(cc1c1cccc2c1cccc2)Cc1cncn1CC1=CC2C(C=C1)OCO2
Isomeric SMILES CN1CCN(CC1)C(=O)c1cn(cc1c1cccc2c1cccc2)Cc1cncn1CC1=CC2C(C=C1)OCO2
InChI InChI=1S/C32H33N5O3/c1-34-11-13-36(14-12-34)32(38)29-20-35(19-28(29)27-8-4-6-24-5-2-3-7-26(24)27)18-25-16-33-21-37(25)17-23-9-10-30-31(15-23)40-22-39-30/h2-10,15-16,19-21,30-31H,11-14,17-18,22H2,1H3
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Mechanism Of Action and Pharmacodynamic Effects Click here for help
FTIs inhibit the C-terminal prenylation of many proteins involved in signal transduction, but are being investigated mainly as inhibitors of deregulated RAS activity in transformed cells. Blocking prenylation of RAS oncogenic proteins prevents their correct membrane tethering, and thereby effects reduced RAS signalling activity and increased cancer cell apoptosis. However, the promise of FTIs has not been bourne out in clinical trials [1], perhaps due to redundancy in the system which sees geranylgeranyltransferase taking over the prenylation process, when farnesyltransferase is inhibited.