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T7204

Sigma-Aldrich

Toremifene citrate salt

≥98% (HPLC)

Synonym(s):

(Z)-2-(4-(4-Chloro-1,2-diphenyl-1-butenyl)phenoxy)-N,N-dimethylethanamine, Acapodene, Fareston, GTx 006, Z-Toremifene

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About This Item

Empirical Formula (Hill Notation):
C26H28ClNO · C6H8O7
CAS Number:
89778-27-8
Molecular Weight:
598.08
MDL number:
MFCD01729016
UNSPSC Code:
51111800
PubChem Substance ID:
329826860
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to off-white

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

SMILES string

OC(=O)CC(O)(CC(O)=O)C(O)=O.CN(C)CCOc1ccc(cc1)C(=C(\CCCl)c2ccccc2)\c3ccccc3

InChI

1S/C26H28ClNO.C6H8O7/c1-28(2)19-20-29-24-15-13-23(14-16-24)26(22-11-7-4-8-12-22)25(17-18-27)21-9-5-3-6-10-21;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-16H,17-20H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/b26-25-;

InChI key

IWEQQRMGNVVKQW-OQKDUQJOSA-N

Gene Information

human ... ESR1(2099) , ESR2(2100)

Related Categories

General description

Toremifene is a triphenylethylene derivative. It exhibits antitumor and antiestrogen effects. Toremifene has estrogen-agonist effects on blood lipids and endometrium.

Application

Toremifene citrate salt has been used:
  • in cell-based ELISA
  • as a positive control to detect its antiviral activity against Ebola virus (EBOV)
  • to treat MCF7 and T47D breast cancer cell lines

Biochem/physiol Actions

Toremifene citrate is an oral selective estrogen receptor modulator (SERM). It is used in advanced (metastatic) breast cancer and being evaluated for prevention of prostate cancer. Toremifene citrate is known to increase bone mineral density in prostate cancer patients undergoing androgen deprivation therapy†.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

Toremifene citrate salt is soluble in DMSO at a concentration that is greater than 10 mg/ml.

Signal Word

Danger

Hazard Statements

H302,H318,H410

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

新产品

Certificates of Analysis (COA)

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Comparison of effects of tamoxifen and toremifene on bone biochemistry and bone mineral density in postmenopausal breast cancer patients
Marttunen MB, et al.
The Journal of Clinical Endocrinology and Metabolism, 83(4), 1158-1162 (1998)
Lack of effect of lamivudine on Ebola virus replication
Hensley LE, et al.
Emerging Infectious Diseases, 21(3), 550-550 (2015)
Hideaki Ogata et al.
Gan to kagaku ryoho. Cancer & chemotherapy, 40(6), 749-753 (2013-07-19)
Third-generation aromatase inhibitors(AIs)are now common in adjuvant hormone therapy for breast cancer in postmenopausal women. However, a suitable treatment has yet to be established for patients who develop cancer recurrence during or after adjuvant AI therapy. This prospective study evaluated
L Kangas et al.
Cancer chemotherapy and pharmacology, 17(2), 109-113 (1986-01-01)
The antitumor effects of a new antiestrogen, Fc-1157a have been studied in vitro and in vivo. In vitro the effect of Fc-1157a was comparable to that of tamoxifen. The effect was dose-dependent, and at concentrations higher than 10(-6) mol/1 Fc-1157a
Toremifene: pharmacologic and pharmacokinetic basis of reversing multidrug resistance.
DeGregorio MW, et al.
Journal of Clinical Oncology, 7(9), 1359-1364 (1989)
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