tamoxifen   

GtoPdb Ligand ID: 1016

Synonyms: ICI-46474 | Nolvadex® | Soltamox®
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.
2D Structure
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Physico-chemical Properties
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
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
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
2-[4-[(Z)-1,2-di(phenyl)but-1-enyl]phenoxy]-N,N-dimethylethanamine
International Nonproprietary Names
INN number INN
3299 tamoxifen
Synonyms
ICI-46474 | Nolvadex® | Soltamox®
Database Links
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
NURSA Ligand 10.1621/84RTZ5I395
PubChem CID 2733526
RCSB PDB Ligand CTX
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Wikipedia Tamoxifen

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Tocris
Tamoxifen
Cat. No. 6342