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
SMILES / InChI / InChIKey
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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 Model List of Essential Medicines (21st List, 2019). Access PDF version.
Is prodrug? Yes
Active form 4-hydroxytamoxifennorendoxifenendoxifen
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
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
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Wikipedia Tamoxifen

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Tocris
Tamoxifen
Cat. No. 6342