| Identification | Back Directory | [Name]
Afimoxifene | [CAS]
68392-35-8 | [Synonyms]
C016601
68392-35-8
AFIMOXIFENE
4-OHT 4-hydroxy
4-Oht hydrotamoxifen
4-Monohydroxytamoxifen
(E/Z)-4-Hydroxy Tamoxifen
Tamoxifen 4-Hydroxy Impurity
Tamoxifen Citrate Impurity 23
4-Hydroxytamoxifen, (E)-isomer
4-Hydroxytamoxifen, (Z)-isomer
Afimoxifene (4-hydroxytamoxifen)
AFIMOXIFENE; 4-OHT 4-HYDROXY; TAMOXIFEN
4-[1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenyl-1-butenyl]phenol
4-[1-[4-[2-(DiMethylaMino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]phenol
Phenol, 4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]- | [Molecular Formula]
C26H29NO2 | [MOL File]
68392-35-8.mol | [Molecular Weight]
387.51 |
| Chemical Properties | Back Directory | [Melting point ]
135-144°C | [Boiling point ]
514.4±50.0 °C(Predicted) | [density ]
1.092 | [storage temp. ]
Refrigerator | [solubility ]
methanol: soluble10mg/mL | [form ]
solution | [pka]
9.38±0.15(Predicted) | [color ]
white to off-white | [Appearance]
white solid | [biological source]
synthetic | [Major Application]
forensics and toxicology
pharmaceutical (small molecule) | [InChI]
1S/2C26H29NO2/c2*1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h2*5-17,28H,4,18-19H2,1-3H3/b26-25+;26-25- | [InChIKey]
ZJLDABGSDWXVGE-BDSXMVAQSA-N | [SMILES]
CC\C(c1ccccc1)=C(/c2ccc(O)cc2)c3ccc(OCCN(C)C)cc3.CC\C(c4ccccc4)=C(\c5ccc(O)cc5)c6ccc(OCCN(C)C)cc6 |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
63-20/21/22 | [Safety Statements ]
22-23-36 | [RIDADR ]
UN1170 - class 3 - PG 2 - Ethanol, solution | [WGK Germany ]
3 | [RTECS ]
SL1210000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Eye Irrit. 2
Repr. 2
Skin Irrit. 2 |
| Hazard Information | Back Directory | [Description]
(E/Z)-4-Hydroxytamoxifen (4-OHT, cis/trans-4-hydroxytamoxifen, afimoxifene) is a selective estrogen receptor (ER) modulator, an active metabolite of tamoxifen. 4-Hydroxytamoxifen is widely used as a research tool for inducible genome manipulation.
4-Hydroxytamoxifen is used in the inducible Cre-LoxP system to control CreER/CreERT2 recombinase activity and trigger tissue-specific gene expression or genome/genetic modification (e.g., gene deletion). 4-Hydroxytamoxifen is a part of the TRAP/TRAP2 (targeted recombination in active populations) systems providing genetic access to neuron activity. It is also used in CRISPR/Cas9 gene editing to activate inactivated Cas9 nuclease.
Also, 4-Hydroxytamoxifen was reported to be an intramembranous lipid peroxidation inhibitor, exhibiting peroxyl radical scavenging activity. | [Chemical Properties]
Off-White Solid | [Uses]
A selective estrogen receptor modulator. | [Definition]
ChEBI: Afimoxifene is a tertiary amino compound that is tamoxifen in which the phenyl group which is in a Z- relationship to the ethyl substituent is hydroxylated at the para- position. It is the active metabolite of tamoxifen. It has a role as an antineoplastic agent, an estrogen receptor antagonist and a metabolite. It is a tertiary amino compound and a member of phenols. It is functionally related to a tamoxifen. | [Brand name]
TamoGel (Ascend Therapeutics). | [General Description]
4-Hydroxytamoxifen is a first generation, selective estrogen receptor modulator (SERM) that functions as an antagonist in breast cancer cells but can display estrogen-like activities in the uterus and bone. | [Biological Activity]
4-hydroxytamoxifen is an estrogen receptor modulator.estrogen receptor can be selectively stimulated or inhibited, providing promising therapeutic opportunities for auto-immune diseases, prostate and breast cancer, as well as depression. | [Biochem/physiol Actions]
Metabolite of the chemotherapeutic drug tamoxifen, exhibiting more potent estrogen agonist/antagonist activity than the parent drug. Also active as intra-membranous inhibitor of lipid peroxidation. | [in vitro]
previous study was conducted to evaluate the effects of tamoxifen and its active metabolite 4-hydroxytamoxifen on isolated rat cardiac myocyte mechanical function and calcium handling. results showed that myocytes treated with 4-hydroxytamoxifen had similarly to tamoxifen-treated cells to both calcium handling and contractility [1]. | [in vivo]
previous animal study compared the extent of dna adduct formation in sd rats treated with seven tamoxifen or 4-hydroxytamoxifen. results showed that the liver weights and microsomal rates were not changed by tamoxifen or 4-hydroxytamoxifen treatment. moreover, the uterine weights were significantly decreased and uterine peroxidase activity was marginally decreased in tamoxifen or 4-hydroxytamoxifen treated rats. in addition, hepatic dna adduct levels in rats treated with 4-hydroxytamoxifen did not differ from control rats. similaryly, the adduct levels in uterus dna from rats treated with tamoxifen or 4-hydroxytamoxifen were not different from those in control rats [2]. | [IC 50]
27 and 18 μm for mcf-7 and mda-mb-231 cell proliferation | [storage]
-20°C | [References]
[1] asp ml,martindale jj,metzger jm. direct, differential effects of tamoxifen, 4-hydroxytamoxifen, and raloxifene on cardiac myocyte contractility and calcium handling. plos one.2013 oct 24;8(10):e78768.
[2] beland fa,mcdaniel lp,marques mm. comparison of the dna adducts formed by tamoxifen and 4-hydroxytamoxifen in vivo. carcinogenesis.1999 mar;20(3):471-7.
[3] lee o et al. a randomized phase ii presurgical trial of transdermal 4-hydroxytamoxifen gel versus oral tamoxifen in women with ductal carcinoma in situ of the breast. clin cancer res.2014 jul 15;20(14):3672-82. |
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