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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2D Structure
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Physico-chemical Properties
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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
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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-
1. Burris TP, Solt LA, Wang Y, Crumbley C, Banerjee S, Griffett K, Lundasen T, Hughes T, Kojetin DJ. (2013)
Nuclear receptors and their selective pharmacologic modulators.
Pharmacol Rev, 65 (2): 710-78. [PMID:23457206]
2. Flockhart DA. 
Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007).
Accessed on 18/11/2014. Modified on 18/11/2014. http://medicine.iupui.edu/clinpharm/ddis/clinical-table/
3. Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA. (1997)
Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta.
Endocrinology, 138 (3): 863-70. [PMID:9048584]
4. Thomas P, Pang Y, Filardo EJ, Dong J. (2005)
Identity of an estrogen membrane receptor coupled to a G protein in human breast cancer cells.
Endocrinology, 146 (2): 624-32. [PMID:15539556]