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elacestrant   Click here for help

GtoPdb Ligand ID: 12339

Synonyms: ER-306323 | ER306323 | Orserdu® | RAD-1901 | RAD1901
Approved drug PDB Ligand
elacestrant is an approved drug (FDA & EMA (2023))
Compound class: Synthetic organic
Comment: Elacestrant is an orally bioactive, selective, non-steroidal dual estrogen receptor degrader (SERD)/selective estrogen receptor modulator (SERM; with antagonist action) [6]. It was developed primarily for antineoplastic potential (via its SERD action at high concentrations) [3]. It has also demonstrated potential to treat the vasomotor symptoms of the menopause with estrogen-like effects detected at low concentrations (SERM activity), but the pharmacology in this setting is very complex [4]. Elacestrant crosses the blood-brain barrier, so is predicted to provide efficacy against breast cancer metastases in the brain.

elacestrant 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 2
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 44.73
Molecular weight 458.29
XLogP 6.6
No. Lipinski's rules broken 1

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 CCNCCc1ccc(cc1)CN(c1cc(OC)ccc1[C@@H]1CCc2c(C1)ccc(c2)O)CC
Isomeric SMILES CCNCCc1ccc(cc1)CN(CC)c1c(ccc(c1)OC)[C@@H]1CCc2c(C1)ccc(c2)O
InChI InChI=1S/C30H38N2O2/c1-4-31-17-16-22-6-8-23(9-7-22)21-32(5-2)30-20-28(34-3)14-15-29(30)26-11-10-25-19-27(33)13-12-24(25)18-26/h6-9,12-15,19-20,26,31,33H,4-5,10-11,16-18,21H2,1-3H3/t26-/m1/s1
InChI Key SIFNOOUKXBRGGB-AREMUKBSSA-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/)
Bioactivity Comments
Elacestrant inhibits estrogen-induced activation of ERα-mediated gene transcription in vitro and in vivo (SERM action), and downregulates ESR1 expression in MCF-7 cells (SERD action) [6]