tamoxifen   Click here for help

GtoPdb Ligand ID: 1016

Synonyms: ICI-46474 | Nolvadex® | Soltamox®
Approved drug PDB Ligand
tamoxifen is an approved drug (FDA (1977))
Compound class: Synthetic organic
Comment: Tamoxifen can be classed as a mixed agonist/antagonist of the estrogen -α and -β receptors, as its activity depends on the tissue in which the receptor is expressed. ChEMBL classify this compound as an ERα modulator, while it is described as a selective estrogen receptor modulator by Burris et al. in their 2013 review [1]. Tamoxifen can be considered as a prodrug as its three main metabolites exhibit higher affinity and specificity than tamoxifen at the ERα and ERβ receptors.
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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

tamoxifen 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 CDK toolkit. 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 8
Topological polar surface area 12.47
Molecular weight 371.22
XLogP 7.14
No. Lipinski's rules broken 1
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.

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Canonical SMILES CCC(=C(c1ccccc1)c1ccc(cc1)OCCN(C)C)c1ccccc1
Isomeric SMILES CC/C(=C(\c1ccccc1)/c1ccc(cc1)OCCN(C)C)/c1ccccc1
InChI InChI=1S/C26H29NO/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3/h5-18H,4,19-20H2,1-3H3/b26-25-
InChI Key NKANXQFJJICGDU-QPLCGJKRSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1977))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
Is prodrug? Yes
Active form 4-hydroxytamoxifen, norendoxifen, endoxifen
IUPAC Name Click here for help
2-[4-[(Z)-1,2-di(phenyl)but-1-enyl]phenoxy]-N,N-dimethylethanamine
International Nonproprietary Names Click here for help
INN number INN
3299 tamoxifen
Synonyms Click here for help
ICI-46474 | Nolvadex® | Soltamox®
Database Links Click here for help
Specialist databases
GPCRdb Ligand tamoxifen
Other databases
BindingDB Ligand 20607
CAS Registry No. 10540-29-1 (source: Scifinder)
ChEBI CHEBI:41774
ChEMBL Ligand CHEMBL83
DrugBank Ligand DB00675
DrugCentral Ligand 2561
GtoPdb PubChem SID 135651233
PubChem CID 2733526
RCSB PDB Ligand CTX
Search Google for chemical match using the InChIKey NKANXQFJJICGDU-QPLCGJKRSA-N
Search Google for chemicals with the same backbone NKANXQFJJICGDU
Search PubMed clinical trials tamoxifen
Search PubMed titles tamoxifen
Search PubMed titles/abstracts tamoxifen
UniChem Compound Search for chemical match using the InChIKey NKANXQFJJICGDU-QPLCGJKRSA-N
UniChem Connectivity Search for chemical match using the InChIKey NKANXQFJJICGDU-QPLCGJKRSA-N
Wikipedia Tamoxifen

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Tocris
Tamoxifen (links to external site)
Cat. No. 6342