GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

orteronel   Click here for help

GtoPdb Ligand ID: 13853

Synonyms: compound (+)-3c [PMID: 21978946] | S-TAK-700 | TAK-700 | TAK700
PDB Ligand
Compound class: Synthetic organic
Comment: Orteronel (TAK-700) is a non-steroidal inhibitor of cytochrome P450 17A1 (CYP17A1) [7]. It was designed to target the enzyme's 17,20-lyase activity (crucial for DHEA and testosterone biosynthesis, including extragonadal androgen production) whilst not altering its 17-hydroxylase catalytic activity (required for corticosterone and aldosterone production) [2]. CYP17A1 inhibition is a molecular mechanism that is expoited for the treatment of advanced castration-resistant prostate cancer (CRPC) [4,6]. For CRPC treatment it would be advantageous to selectively inhibit androgen biosynthesis, whilst limiting reductions in corticosterone and aldosterone production.
Click here for help

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.

✖

View interactive charts of activity data across species
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 64.93
Molecular weight 307.35
XLogP 0.49
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
Click here for help

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/)

✖
Canonical SMILES CNC(=O)C1=CC=C2C=C(C=CC2=C1)[C@]3(CCN4C=NC=C34)O
Isomeric SMILES CNC(=O)C1=CC2=C(C=C1)C=C(C=C2)[C@]3(CCN4C3=CN=C4)O
InChI InChI=1S/C18H17N3O2/c1-19-17(22)14-3-2-13-9-15(5-4-12(13)8-14)18(23)6-7-21-11-20-10-16(18)21/h2-5,8-11,23H,6-7H2,1H3,(H,19,22)/t18-/m0/s1
InChI Key OZPFIJIOIVJZMN-SFHVURJKSA-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
Orteronel (TAK-700) was progressed to clinical trials in castration-resistant prostate cancer (CRPC). Development was terminated at phase 3 due to lack of efficacy.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01707966 Orteronel Maintenance Therapy in Patients With Metastatic Castration Resistant Prostate Cancer and Non-progressive Disease After First-line Docetaxel Therapy Phase 3 Interventional Swiss Group for Clinical Cancer Research 1
NCT01193244 Study Comparing Orteronel Plus Prednisone in Participants With Chemotherapy-Naive Metastatic Castration-Resistant Prostate Cancer Phase 3 Interventional Takeda 5