toremifene   Click here for help

GtoPdb Ligand ID: 4325

Synonyms: Fareston® | Farestone® | FC-1157a
Approved drug PDB Ligand
toremifene is an approved drug (EMA (1996), FDA (1997))
Compound class: Synthetic organic
Comment: Toremifene is an orally active, selective estrogen receptor modulator (SERM).

toremifene 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 1
Hydrogen bond donors 0
Rotatable bonds 9
Topological polar surface area 12.47
Molecular weight 405.19
XLogP 6.85
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 ClCCC(=C(c1ccccc1)c1ccc(cc1)OCCN(C)C)c1ccccc1
Isomeric SMILES ClCC/C(=C(\c1ccccc1)/c1ccc(cc1)OCCN(C)C)/c1ccccc1
InChI InChI=1S/C26H28ClNO/c1-28(2)19-20-29-24-15-13-23(14-16-24)26(22-11-7-4-8-12-22)25(17-18-27)21-9-5-3-6-10-21/h3-16H,17-20H2,1-2H3/b26-25-
InChI Key XFCLJVABOIYOMF-QPLCGJKRSA-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
Used in the treatment of metastatic breast cancer in post-menopausal women with estrogen-receptor-positive or receptor-unknown tumours. Being investigated for the treatment of prostate cancer [1]. Follow this link to view a list of clinical trials assessing toremifene in prostate cancer, registered with ClinicalTrials.gov.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Estrogen receptor modulator. In its use in breast cancer treatment, the antitumour effect is believed to arise from its antiestrogenic effect.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)