relugolix   Click here for help

GtoPdb Ligand ID: 5586

Synonyms: Orgovyx® | Ryeqo® (relugolix-estradiol-norethisterone acetate) | TAK 385 | TAK-385
Approved drug
relugolix is an approved drug (FDA (2020), EMA (2021))
Compound class: Synthetic organic
Comment: Relugolix (TAK-385) is a non-peptide, orally active GnRH receptor antagonist [1]. Administration suppresses the hypothalamic-pituitary-gonadal axis. In males this causes chemical castration.
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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
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 7
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 160.33
Molecular weight 623.18
XLogP 4.28
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 CONC(=O)Nc1ccc(cc1)c1sc2c(c1CN(C)C)c(=O)n(c(=O)n2Cc1c(F)cccc1F)c1ccc(nn1)OC
Isomeric SMILES CONC(=O)Nc1ccc(cc1)c1sc2c(c1CN(C)C)c(=O)n(c(=O)n2Cc1c(F)cccc1F)c1ccc(nn1)OC
InChI InChI=1S/C29H27F2N7O5S/c1-36(2)14-19-24-26(39)38(22-12-13-23(42-3)34-33-22)29(41)37(15-18-20(30)6-5-7-21(18)31)27(24)44-25(19)16-8-10-17(11-9-16)32-28(40)35-43-4/h5-13H,14-15H2,1-4H3,(H2,32,35,40)
InChI Key AOMXMOCNKJTRQP-UHFFFAOYSA-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
Relugolix (TAK-385) was evaluated in several Phase 3 clinical trials. In women it was progressed as a therapy for endometriosis related pain and heavy menstrual bleeding associated with uterine fibroids. In males it was evaluated in prostate cancer. Click here to view ClinicalTrials.gov's full list of registered TAK-385 trials. In December 2020, the FDA approved relugolix as the first oral GnRH receptor antagonist-based treatment for advanced prostate cancer. In July 2021 the EMA approved the combination drug Ryeqo® (relugolix+estradiol+norethisterone acetate) as a treatment for leiomyoma. The EMA authorised use of single agent relugolix for treatment of prostatic neoplasms in 2022.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Administration of TAK-385 suppresses the hypothalamic-pituitary-gonadal axis [1]. In males this causes chemical castration (testosterone suppression) and this action has potential for treating hormone sensitive prostate cancer.