lanabecestat   Click here for help

GtoPdb Ligand ID: 7789

Synonyms: AZD 3293 | AZD-3293 | LY3314814
Compound class: Synthetic organic
Comment: Lanabecestat (AZD3293) is an oral, potent and selective small molecule inhibitor of BACE1 being developed by AstraZeneca and Eli Lilly [4] . It is now proceeding to Phase III trials [3]. Note our initial chemical assignment was based on the crystallisation data in US20140031379 [2] but the name is now attached to two CIDs, the one designated in this entry with correct stereoisomer and the flat form as PubChem CID 57404290
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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

lanabecestat 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 5
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 72.86
Molecular weight 412.23
XLogP 4.24
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 CC#Cc1cncc(c1)c1ccc2c(c1)C1(N=C(C(=N1)C)N)C1(C2)CCC(CC1)OC
Isomeric SMILES CC#Cc1cncc(c1)c1ccc2c(c1)[C@]1(N=C(C(=N1)C)N)C1(C2)CCC(CC1)OC
InChI InChI=1S/C26H28N4O/c1-4-5-18-12-21(16-28-15-18)19-6-7-20-14-25(10-8-22(31-3)9-11-25)26(23(20)13-19)29-17(2)24(27)30-26/h6-7,12-13,15-16,22H,8-11,14H2,1-3H3,(H2,27,30)/t22?,25?,26-/m0/s1
InChI Key WKDNQONLGXOZRG-BOPKNSRXSA-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/)
No information available.
Summary of Clinical Use Click here for help
Results from Phase 1 study NCT01795339 show significantly and dose-dependently reduced levels of amyloid beta in the cerebro-spinal fluid of Alzheimer’s patients and healthy volunteers [5]. Phase II/III study NCT02245737 is underway in patients with early Alzheimer´s disease.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01795339 A Two-part Multiple Dose Study to Assess the Safety and Effects of AZD3293 in Healthy Elderly and Alzheimer's Patients Phase 1 Interventional AstraZeneca
NCT02245737 An Efficacy and Safety Study of Lanabecestat (LY3314814) in Early Alzheimer's Disease Phase 2/Phase 3 Interventional AstraZeneca