4'-Hydroxytamoxifen
Basic information
- CAS
82413-23-8- Standard SMILES
CC/C(=C(\c1ccccc1)c1ccc(OCCN(C)C)cc1)c1ccc(O)cc1- InChIKey
DODQJNMQWMSYGS-QPLCGJKRSA-N- Molecular formula
- C26H29NO2
- Average molar mass
- 387.5 g/mol
- Monoisotopic mass
- 387.21982917
Overview
4-hydroxytamoxifen is a selective estrogen receptor modulator. It is currently in the development process to work as a potential breast hyperplasia treatment.
Names & identifiers
- Preferred name
- 4'-Hydroxytamoxifen
- IUPAC
- 4-[(Z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-1-phenylbut-1-en-2-yl]phenol
- English name
- 4Hydroxy Tamoxifen
- Molecular formula
- C26H29NO2
- Molecular weight
- 387.51
Names & synonyms
4'-hydroxytamoxifen82413-23-8DTXSID00873019RefChem:1069047DTXCID908205324'-Hydroxy tamoxifen4-Hydroxy-tamoxifen4-[(Z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-1-phenylbut-1-en-2-yl]phenol4 inverted exclamation mark -hydroxy Tamoxifen4'-Hydroxy Tamoxifen (contains up to 10% E isomer)trans-HydroxytamoxifenNCGC00091028-01
Show more names
4’-hydroxy TamoxifenTamoxifen Citrate Impurity 18Tamoxifen Citrate Impurity 13 (4'-Hydroxytamoxifen)4-[(1Z)-1-[[4-[2-(Dimethylamino)ethoxy]phenyl]phenylmethylene]propyl]phenolPhenol, 4-[(1Z)-1-[[4-[2-(dimethylamino)ethoxy]phenyl]phenylmethylene]propyl]-
4??-hydroxy Tamoxifen(Z)-4'-hydroxytamoxifenCHEMBL10041GTPL2817orb1704736SCHEMBL21655034'-Hydroxytamoxifen (Standard)CHEBI:231618
Database identifiers
Properties
Computed structural properties
- XLogP
- 6.8
- Topological polar surface area
- 32.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 8
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 493
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Melting point
- 150 · 150-153°C
- Boiling point
- 514.4 · 514.4±50.0 °C(Predicted)
- Density
- 1.092 · 1.092±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Amber Vial, -20°C Freezer, Under Inert Atmosphere
- solubility
- Chloroform (Slightly), Dichloromethane, Methanol (Slightly)
- form
- Solid
- pka
- 10.32 · 10.32±0.15(Predicted)
- color
- White to Off-White
- Stability
- Light Sensitive
Chemistry & industry
Pharmacology
Metabolism/Metabolites4'-Hydroxytamoxifen is a known human metabolite of tamoxifen.
Applications
Description4’-hydroxy Tamoxifen is one of five main phase I metabolites of tamoxifen , a well-known estrogen receptor antagonist in breast but partial estrogen receptor agonist in endometrium. 4’-hydroxy Tamoxifen is a product of cytochrome P450 (CYP)2D6 and CYP2B6 activity. With the addition of a hydroxyl group, 4’-hydroxy tamoxifen has been shown to have a higher affinity for estrogen receptors compared to tamoxifen. At 10-100 μM, 4’-hydroxy tamoxifen is cytotoxic, in a non-apoptotic manner, to HEC-1B and HEC-1A human endometrial adenocarcinoma cell lines.
UsesA metabolite of Tamoxifen (T006000).
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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